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PMC:7784829 / 12424-26386 JSONTXT

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LitCovid-sentences

Id Subject Object Predicate Lexical cue
T101 0-25 Sentence denotes Molecular docking studies
T102 26-137 Sentence denotes The three-dimensional structure of the SARS-CoV spike protein and SARS-CoV-2 Spike protein RBD has been solved.
T103 138-277 Sentence denotes The PDB files of the SARS-CoV spike protein (6CRV) and the Spike protein RBD of the SARS-CoV-2 (6M0J) was downloaded from the PDB databank.
T104 278-423 Sentence denotes These structures were used to predict the ability of the binding of curcumin and its derivatives to the spike proteins of the two corona viruses.
T105 424-529 Sentence denotes Curcumin and 24 of its derivatives (Figure 1 and Supplementary Figure 2) were docked on to 6CRV and 6M0J.
T106 530-748 Sentence denotes Tables 2 and 3 gives the binding energies of curcumin and its derivatives with 6CRV (binding energies ranged from −10.98 to −5.12 kcal/mol) and with 6M0J (binding energies ranged −10.01 to −5.33 kcal/mol) respectively.
T107 749-1134 Sentence denotes Visual examination of the computationally docked optimal binding poses of curcumin and its derivatives on 6CRV and 6MOJ revealed the important role of various types of interactions viz. hydrogen bonding and hydrophobic interactions, including π–π stacking, π–cation, and π–σ interactions in the stability of the binding of the curcumin/derivatives to the spike protein (6CRV and 6M0J).
T108 1135-1215 Sentence denotes All compounds showed one or more hydrogen bonds with 6CRV and 6M0J except a few.
T109 1216-1225 Sentence denotes Figure 2.
T110 1227-1686 Sentence denotes Molecular docking of Bis-demethoxy curcumin on SARS-CoV spike protein (6CRV). (A) 3 D structure of SARS-CoV Spike Glycoprotein Macromolecule (6CRV). (B) Binding Interaction of Bis-demethoxy curcumin with amino acid residues of SARS-CoV Spike glycoprotein (PDB ID-6CRV). (C) Superimposed binding mode of Bis-demethoxy curcumin with SARS-CoV Spike protein. (D) 2 D representation of the binding interaction of Bis-demethoxy curcumin with SARS-CoV Spike protein.
T111 1687-1695 Sentence denotes Table 2.
T112 1697-1790 Sentence denotes Molecular docking results of curcumin and its derivatives with SARS-CoV Spike protein (6CRV).
T113 1791-1857 Sentence denotes The top hits with the binding energy lesser than -8.4 are in bold.
T114 1858-1939 Sentence denotes Compound Binding Energy (ΔG) Ligand Efficiency Intermolecular energy XPH-Bond
T115 1940-1983 Sentence denotes Curcumin –10.1 –0.14 –8.24 –10.9724
T116 1984-2019 Sentence denotes BHBC –8.28 –0.13 –7.87 –3.42239
T117 2020-2054 Sentence denotes MNC –8.01 –0.43 –6.98 –8.01452
T118 2055-2095 Sentence denotes BDMC –10.98 –0.18 –8.94 –14.0467
T119 2096-2121 Sentence denotes 1 –5.12 –0.25 –4.17 0
T120 2122-2158 Sentence denotes 2 –8.55 –0.41 –6.56 –18.4317
T121 2159-2191 Sentence denotes 3 –6.56 –0.21 –4.92 –11.1148
T122 2192-2228 Sentence denotes 4 –8.69 –0.13 –6.94 –19.1539
T123 2229-2261 Sentence denotes 5 –7.03 –0.19 –5.93 –8.47153
T124 2262-2294 Sentence denotes 6 –6.59 –0.36 –5.12 –7.41531
T125 2295-2327 Sentence denotes 7 –7.96 –0.21 –6.14 –7.98548
T126 2328-2360 Sentence denotes 8 –7.55 –0.19 –5.14 –6.14537
T127 2361-2386 Sentence denotes 9 –6.91 –0.21 –5.18 0
T128 2387-2420 Sentence denotes 10 –7.75 –0.21 –6.14 –6.73473
T129 2421-2454 Sentence denotes 11 –8.02 –0.19 –6.19 –17.2465
T130 2455-2488 Sentence denotes 12 –7.85 –0.38 –6.25 –14.6321
T131 2489-2522 Sentence denotes 13 –5.94 –0.29 –4.12 –11.3576
T132 2523-2560 Sentence denotes 14 –8.75 –0.25 –7.19 –21.1412
T133 2561-2595 Sentence denotes 15 –7.87 –0.38 –7.26 –0.473228
T134 2596-2634 Sentence denotes 16 –8.47 –0.25 –6.88 –8.458912
T135 2635-2670 Sentence denotes DMC –7.89 –0.21 –6.41 –10.47057
T136 2671-2705 Sentence denotes FAC –7.17 –0.36 –5.15 –9.14873
T137 2706-2740 Sentence denotes IBC –7.91 –0.23 –7.17 –6.90341
T138 2741-2775 Sentence denotes IVC –7.43 –0.44 –6.67 –19.9864
T139 2776-2810 Sentence denotes SYC –6.82 –0.26 –5.45 –9.44678
T140 2811-2831 Sentence denotes Abbreviations: BHBC:
T141 2832-2886 Sentence denotes 3-5-di-tert-butyl-4-hydroxybenzaldehyde curcumin, MNC:
T142 2887-2929 Sentence denotes 4-methoxy-1-naphthaldehyde curcumin, BDMC:
T143 2930-2958 Sentence denotes Bis-demethoxy curcumin, DMC:
T144 2959-2983 Sentence denotes Demethoxy curcumin, FAC:
T145 2984-3011 Sentence denotes Ferulic-acid curcumin, IBC:
T146 3012-3036 Sentence denotes Ibuprofen curcumin, IVC:
T147 3037-3063 Sentence denotes Isovanillin curcumin, SYC:
T148 3064-3088 Sentence denotes Syringaldehyde curcumin.
T149 3089-3097 Sentence denotes Table 3.
T150 3099-3219 Sentence denotes Molecular docking analysis of curcumin and its derivatives with SARS-CoV-2 Spike protein Receptor binding domain (6M0J).
T151 3220-3286 Sentence denotes The top hits with the binding energy lesser than -8.4 are in bold.
T152 3287-3368 Sentence denotes Compound Binding Energy (ΔG) Ligand Efficiency Intermolecular energy XPH-Bond
T153 3369-3412 Sentence denotes Curcumin –9.81 –0.15 –8.35 –15.1512
T154 3413-3441 Sentence denotes BHBC −5.33 –0.13 –7.96 0
T155 3442-3476 Sentence denotes MNC –7.96 –0.27 –7.38 –4.24687
T156 3477-3517 Sentence denotes BDMC –10.01 –0.12 –9.18 –13.9824
T157 3518-3550 Sentence denotes 1 –7.58 –0.36 –6.19 –18.3489
T158 3551-3585 Sentence denotes 2 –8.81 –0.31 –8.38 1.2654
T159 3586-3618 Sentence denotes 3 –6.14 –0.34 –5.45 –6.95102
T160 3619-3655 Sentence denotes 4 –8.88 –0.18 –7.98 –14.0321
T161 3656-3687 Sentence denotes 5 –6.23 –0.26 –5.88 –3.5891
T162 3688-3720 Sentence denotes 6 –7.16 –0.37 –6.15 –10.1688
T163 3721-3753 Sentence denotes 7 –6.89 –0.25 –5.98 –9.12515
T164 3754-3786 Sentence denotes 8 –5.49 –0.12 –3.90 –5.92265
T165 3787-3819 Sentence denotes 9 –6.92 –0.18 –6.22 –6.96719
T166 3820-3849 Sentence denotes 10 –7.03 –0.24 –6.33 –7.0
T167 3850-3883 Sentence denotes 11 –6.88 –0.27 –6.23 –6.44363
T168 3884-3916 Sentence denotes 12 –7.95 –0.41 –5.70 –2.5581
T169 3917-3950 Sentence denotes 13 –6.11 –0.39 –5.42 –7.34943
T170 3951-3984 Sentence denotes 14 –7.45 –0.19 –6.40 –10.5367
T171 3985-4018 Sentence denotes 15 –5.74 –0.39 –5.51 –2.36748
T172 4019-4052 Sentence denotes 16 –7.83 –0.27 –7.48 –6.64321
T173 4053-4087 Sentence denotes DMC –5.98 –0.19 –5.38 –5.99913
T174 4088-4122 Sentence denotes FAC –5.85 –0.38 –5.25 –6.46613
T175 4123-4157 Sentence denotes IBC –6.65 –0.15 –6.20 –1.52841
T176 4158-4196 Sentence denotes IVC –8.96 –0.43 –7.73 –12.2707
T177 4197-4230 Sentence denotes SYC –5.87 –0.29 –5.43 –4.4411
T178 4231-4251 Sentence denotes Abbreviations: BHBC:
T179 4252-4306 Sentence denotes 3-5-di-tert-butyl-4-hydroxybenzaldehyde curcumin, MNC:
T180 4307-4349 Sentence denotes 4-methoxy-1-naphthaldehyde curcumin, BDMC:
T181 4350-4378 Sentence denotes Bis-demethoxy curcumin, DMC:
T182 4379-4403 Sentence denotes Demethoxy curcumin, FAC:
T183 4404-4431 Sentence denotes Ferulic-acid curcumin, IBC:
T184 4432-4456 Sentence denotes Ibuprofen curcumin, IVC:
T185 4457-4483 Sentence denotes Isovanillin curcumin, SYC:
T186 4484-4508 Sentence denotes Syringaldehyde curcumin.
T187 4509-4798 Sentence denotes In 6CRV, it was found that ARG99, GLY100, TRP 101, ILE116, ILE117, ASN118, VAL123, MET144, SER165, ASP166, PHE168, ARG183, PHE185, LYS198, ILE219, PHE220 were the major amino acids involved in hydrogen bonding, hydrophobic and van der Waals interaction with most of the curcumin compounds.
T188 4799-4921 Sentence denotes However, majority of the curcumin compounds exhibited hydrogen bonding with ARG99, MET144, LYS198 except compound 1 and 9.
T189 4922-5165 Sentence denotes In addition, all the compounds exhibited hydrophobic (π–π stacking, π–cation, and π–σ) interactions with ASP166, VAL123, PHE185 and van der Waals interaction with GLY100, TRP 101, ILE117, ASN118, ARG183, ILE116, PHE168, SER165, PHE220, ILE219.
T190 5166-5325 Sentence denotes All compounds showed one or more hydrogen bonding interactions with spike RBD of the SARS-CoV-2 (6M0J) except 3-5-di-tert-butyl-4-hydroxybenzaldehyde curcumin.
T191 5326-5576 Sentence denotes It was found that ARG355, TYR396, PRO426, ASP428, THR430, GLY431, PHE429, PHE 464, GLU516, SER514, LEU517 and PHE515 were the major amino acids involved in hydrogen bonding hydrophobic and van der Waals interaction with the all of curcumin compounds.
T192 5577-5677 Sentence denotes However, majority of the curcumin compounds exhibit hydrogen bonding with ARG355, LEU517 and THR430.
T193 5678-5871 Sentence denotes In addition, the compounds exhibited hydrophobic (π–π stacking, π–cation, and π–σ) and van der Waals interactions with PHE464, GLY431, GLU516, SER514, PHE515, TYR396, PRO426, ASP428 and PHE429.
T194 5872-6022 Sentence denotes The curcumin derivative with the best binding affinity was Bis-demethoxycurcumin for both 6CRV (ΔG = −10.98 kcal/mol) and 6M0J (ΔG = −10.01 kcal/mol).
T195 6023-6139 Sentence denotes The native compound, curcumin, demonstrated a binding energy of −9.81 kcal/mol for 6M0J and −10.1 kcal/mol for 6CRV.
T196 6140-6280 Sentence denotes Binding mode of Bis-demethoxycurcumin with SARS-CoV Spike protein and SARS-CoV-2 Spike protein RBD is shown in Figure 2 and 3, respectively.
T197 6281-6290 Sentence denotes Figure 3.
T198 6292-6808 Sentence denotes Molecular docking of Bis-demethoxy curcumin on SARS-CoV-2 spike protein receptor binding domain (6M0J). (A) 3D structure of SARS-CoV-2 spike protein RBD bound with ACE2 protein Macromolecule. (B) Binding Interaction of Bis-demethoxy curcumin with amino acid residue of spike protein RBD of SARS-CoV-2 (PDB ID-6M0J). (C) Superimposed binding mode of Bis-demethoxy curcumin, docked with SARS-CoV-2 spike protein RBD. (D) 2D representation of the binding interaction of Bis-demethoxy curcumin with SARS-CoV-2 spike RBD.
T199 6810-6873 Sentence denotes In-silico drug-likeness and pharmacokinetic property prediction
T200 6874-7011 Sentence denotes All the structures used for docking were analysed for in silico drug-likeness based on the Lipinski’s rules using pkCSM server (Table 4).
T201 7012-7168 Sentence denotes The lipophilicity (expressed as LogP) predicted for all the compounds were found to be well above the traditionally cut-off value of 5 used for drug design.
T202 7169-7322 Sentence denotes Curcumin and its derivatives, used in this study, show suitable MW values (MW < 500) essential for a successful penetration through biological membranes.
T203 7323-7449 Sentence denotes The surface area (SA) for all the compounds was observed to be in the range 115.89 − 240.65 Å2 which is well within the limit.
T204 7450-7707 Sentence denotes All compounds, except 5-di-tert-butyl-4-hydroxybenzaldehyde curcumin (BHBC), 4-methoxy-1-naphthaldehyde curcumin (MNC), Syringaldehyde curcumin (SYC) and compound-16, fall into the appropriate range indicating good bioavailability of the candidate molecule.
T205 7708-7852 Sentence denotes The number of hydrogen bond acceptors (HBA, ≤10) and donors (HBD, ≤5) for all the compounds were in accordance with the Lipinski’s rule of five.
T206 7853-7861 Sentence denotes Table 4.
T207 7863-7929 Sentence denotes In-silico prediction of drug-likeness for curcumin derivatives[a].
T208 7930-7992 Sentence denotes Compound MW LogP SA HBA HBD nviolations Rotatable bonds
T209 7993-8030 Sentence denotes BHBC 534.78 8.93 236.0 4 3 1 6
T210 8031-8069 Sentence denotes MNC 538.59 6.14 232.11 7 2 1 11
T211 8070-8108 Sentence denotes BDMC 308.33 3.83 133.51 4 3   5
T212 8109-8145 Sentence denotes 1 270.353 4.21 115.89 3 1   4
T213 8146-8182 Sentence denotes 2 332.739 3.79 136.57 5 4   4
T214 8183-8219 Sentence denotes 3 314.337 3.77 133.64 5 4   4
T215 8220-8255 Sentence denotes 4 322.36 4.36 139.56 3 3   4
T216 8256-8292 Sentence denotes 5 364.441 4.93 159.62 4 0   5
T217 8293-8329 Sentence denotes 6 320.388 4.95 141.45 4 3   1
T218 8330-8365 Sentence denotes 7 325.32 3.60 138.02 5 1   6
T219 8366-8402 Sentence denotes 8 329.193 4.45 125.75 2 1   4
T220 8403-8439 Sentence denotes 9 462.181 5.24 164.71 7 2   0
T221 8440-8477 Sentence denotes 10 351.358 4.13 149.74 4 5   1
T222 8478-8515 Sentence denotes 11 360.375 5.07 149.89 2 1   3
T223 8516-8553 Sentence denotes 12 419.565 6.24 185.40 9 4   1
T224 8554-8591 Sentence denotes 13 389.495 5.22 171.67 4 4   1
T225 8592-8629 Sentence denotes 14 342.778 3.81 143.82 4 2   2
T226 8630-8667 Sentence denotes 15 469.629 4.38 208.20 6 5   1
T227 8668-8706 Sentence denotes 16 486.564 6.19 211.58 11 6 1 0
T228 8707-8745 Sentence denotes DMC 342.391 3.20 146.43 5 2   9
T229 8746-8784 Sentence denotes FAC 550.604 4.7 232.81 9 2   15
T230 8785-8824 Sentence denotes IBC 556.655 5.24 240.62 7 1   15
T231 8825-8864 Sentence denotes IVC 504.535 4.69 214.22 8 3   11
T232 8865-8904 Sentence denotes SYC 430.453 3.77 180.12 10 8 1 3
T233 8905-9120 Sentence denotes [a]  MW = Molecular weight, LogP = octanol-water partition coefficient, SA = Surface Area, HBA = Number of hydrogen bond acceptor, HBD = Number of hydrogen bond donor, nviolations = violations from Lipinski’s rule.
T234 9121-9126 Sentence denotes BHBC:
T235 9127-9181 Sentence denotes 3-5-di-tert-butyl-4-hydroxybenzaldehyde curcumin, MNC:
T236 9182-9224 Sentence denotes 4-methoxy-1-naphthaldehyde curcumin, BDMC:
T237 9225-9253 Sentence denotes Bis-demethoxy curcumin, DMC:
T238 9254-9278 Sentence denotes Demethoxy curcumin, FAC:
T239 9279-9306 Sentence denotes Ferulic-acid curcumin, IBC:
T240 9307-9331 Sentence denotes Ibuprofen curcumin, IVC:
T241 9332-9358 Sentence denotes Isovanillin curcumin, SYC:
T242 9359-9383 Sentence denotes Syringaldehyde curcumin.
T243 9384-9539 Sentence denotes Additionally, a variety of key ADMET (Absorption, Distribution, Metabolism and Excretion) properties have also been calculated with the aid of pkCSMserver.
T244 9540-9574 Sentence denotes The results are listed in Table 5.
T245 9575-9877 Sentence denotes All curcumin derivatives showed moderate to high water solubility ranging from −2.91 log mol/L (BHBC) to −6.99 log mol/L (compound-12), in addition to high Caco-2 permeability (permeation > 0.90) except compound BHBC and MNC (permeation = 0.67 and 0.43 respectively) which showed moderate permeability.
T246 9878-10001 Sentence denotes Intestinal absorption (IA) has been found to be greater than 85% indicating good permeation across the intestinal membrane.
T247 10002-10090 Sentence denotes Further, all curcumin compounds showed good permeation through skin (permeation > −2.5).
T248 10091-10325 Sentence denotes Additionally, all curcumin compounds showed no inhibition towards P-glycoprotein I and P-glycoprotein II, except compounds BHBC, MNC, compound-13 and Ferrulic acid curcumin (FAC) which demonstrated inhibition towards P-glycoprotein I.
T249 10326-10463 Sentence denotes Furthermore, all curcumin compounds showed poor BBB permeability and moderate CNS permeability except Isovanillin curcumin (IVC) and SYC.
T250 10464-10637 Sentence denotes All showed inhibition towards the metabolizing enzyme CYP3A4 except BHBC, compounds-8, -11, -14, -15 and -16, while except compound-15, all showed inhibition towards CYP2C9.
T251 10638-10790 Sentence denotes All curcumin derivatives were found to show the total clearance in the range 0.10 log mL/min/kg (compound-1 and -4) to 1.01 log mL/min/kg (compound-15).
T252 10791-10999 Sentence denotes Further, all curcumin derivatives except compound 15 were found to act as OCT2 substrate, thus indicating that these compounds will not have any adverse interactions and no negative effect on renal clearance.
T253 11000-11008 Sentence denotes Table 5.
T254 11010-11064 Sentence denotes In-silico ADME prediction for curcumin derivatives[a].
T255 11065-11118 Sentence denotes Comp Absorption Distribution Metabolism Excretion
T256 11119-11186 Sentence denotes   WS CP IA SP PI-1 PI-2 VD FU BBB CNS CI-1 CI-2 TC RS
T257 11187-11274 Sentence denotes BHBC –2.91 0.67 88.62 –2.73 Yes Yes –0.39 0.31 –0.67 –0.85 No Yes 0.15 No
T258 11275-11360 Sentence denotes MNC –3.64 0.43 100 –2.73 Yes Yes –1.45 0.33 –0.39 –2.73 Yes Yes 0.26 No
T259 11361-11447 Sentence denotes BDMC –4.43 1.01 95.92 –2.99 No No –0.22 0.08 –0.72 –2.11 Yes Yes 0.12 No
T260 11448-11529 Sentence denotes 1 –4.66 1.25 91.80 –2.51 No No 0.18 0.06 0.01 –1.45 Yes Yes 0.10 No
T261 11530-11613 Sentence denotes 2 –3.23 0.93 89.16 –2.76 No No –0.07 0.12 –1.07 –2.29 Yes Yes 0.05 No
T262 11614-11697 Sentence denotes 3 –3.19 0.94 89.70 –2.76 No No –0.02 0.13 –1.06 –2.27 Yes Yes 0.06 No
T263 11698-11777 Sentence denotes 4 –4.11 0.92 87.64 –3.07 No No 0.09 0 –0.74 –1.85 Yes Yes 0.10 No
T264 11778-11857 Sentence denotes 5 –6.39 1.06 94.85 –2.49 No No 0.25 0 –0.03 –1.30 Yes Yes 0.22 No
T265 11858-11937 Sentence denotes 6 –5.42 1.43 90.49 –2.73 No No 0.05 0 –0.33 –1.29 Yes Yes 0.23 No
T266 11938-12017 Sentence denotes 7 –4.54 1.04 91.97 –2.73 No No –0.37 0 0.28 –2.20 Yes Yes 0.13 No
T267 12018-12095 Sentence denotes 8 –5.09 1.66 90.44 –2.29 No No 0.27 0 0.16 –1.47 No Yes 0.14 No
T268 12096-12174 Sentence denotes 9 –7.03 1.13 93.34 –2.51 No No 0.37 0 0.46 –1.26 Yes Yes 0.26 No
T269 12175-12256 Sentence denotes 10 –4.89 0.94 91.50 –2.74 No No –0.04 0 –0.24 –1.93 Yes Yes 0.11 No
T270 12257-12335 Sentence denotes 11 –5.93 1.28 89.16 –2.59 No No 0.36 0 0.66 –1.40 No Yes 0.13 No
T271 12336-12416 Sentence denotes 12 –6.99 1.02 91.30 –2.75 No No 0.66 0 –0.32 –1.85 Yes Yes 1.04 No
T272 12417-12499 Sentence denotes 13 –5.42 1.27 92.76 –2.80 Yes Yes 0.54 0 –0.02 –1.58 Yes Yes 0.26 No
T273 12500-12583 Sentence denotes 14 –4.20 1.12 90.31 –2.92 No No –0.04 0.01 –0.31 –1.33 No Yes 0.08 No
T274 12584-12666 Sentence denotes 15 –3.76 0.97 88.86 –2.79 No No 1.90 0.16 –0.20 –1.26 No No 1.01 Yes
T275 12667-12750 Sentence denotes 16 –6.92 0.90 94.67 –2.73 No No –0.59 0.07 –0.72 –2.62 No Yes 0.41 No
T276 12751-12836 Sentence denotes DMC –3.95 0.99 92.03 –2.74 No No –0.06 0.12 –0.23 –2.66 Yes Yes 0.32 No
T277 12837-12924 Sentence denotes FAC –4.02 1.41 83.68 –2.76 Yes Yes –0.58 0.24 –0.91 –3.26 Yes Yes 0.55 No
T278 12925-13010 Sentence denotes IBC –4.36 0.91 91.72 –2.73 No No –0.88 0.18 –0.53 –2.77 Yes Yes 0.62 No
T279 13011-13096 Sentence denotes IVC –3.95 0.96 89.31 –2.73 No No –0.60 0.24 –1.37 –3.02 Yes Yes 0.16 No
T280 13097-13181 Sentence denotes SYC –3.89 1.01 89.15 –2.73 No No 0.28 0.17 –1.47 –3.14 Yes Yes 0.23 No
T281 13182-13699 Sentence denotes [a]  Abbreviations: WS—Water solubility (log mol/L), CP—Caco2 permeability (log Papp in 10-6 cm/s), IA—Human intestinal absorption (% Absorbed), SP—Skin permeability (log Kp),PI-1—P-glycoprotein I inhibitor, PI-2—P-glycoprotein II inhibitor, VD—Human volume ofdistribution (log L/kg), FU—Fraction unbound (human) (Fu), BBB—BBB permeability (logBB), CNS—CNS permeability (log PS), CI-1—CYP3A4 inhibitor, CI-2—CYP2C9 inhibitor,TC—Total clearance (log mL/min/kg), RS—Renal OCT2 (organic cation transporter 2) substrate.
T282 13700-13705 Sentence denotes BHBC:
T283 13706-13760 Sentence denotes 3-5-di-tert-butyl-4-hydroxybenzaldehyde curcumin, MNC:
T284 13761-13803 Sentence denotes 4-methoxy-1-naphthaldehyde curcumin, BDMC:
T285 13804-13832 Sentence denotes Bis-demethoxy curcumin, DMC:
T286 13833-13857 Sentence denotes Demethoxy curcumin, FAC:
T287 13858-13885 Sentence denotes Ferulic-acid curcumin, IBC:
T288 13886-13910 Sentence denotes Ibuprofen curcumin, IVC:
T289 13911-13937 Sentence denotes Isovanillin curcumin, SYC:
T290 13938-13962 Sentence denotes Syringaldehyde curcumin.

LitCovid-PubTator

Id Subject Object Predicate Lexical cue tao:has_database_id
297 103-108 Gene denotes Spike Gene:43740568
298 197-202 Gene denotes Spike Gene:43740568
299 1104-1109 Gene denotes spike Gene:43740568
300 74-79 Gene denotes spike Gene:43740568
301 382-387 Gene denotes spike Gene:43740568
302 168-173 Gene denotes spike Gene:43740568
303 65-73 Species denotes SARS-CoV Tax:694009
304 92-102 Species denotes SARS-CoV-2 Tax:2697049
305 159-167 Species denotes SARS-CoV Tax:694009
306 222-232 Species denotes SARS-CoV-2 Tax:2697049
307 346-354 Chemical denotes curcumin MESH:D003474
308 424-432 Chemical denotes Curcumin MESH:D003474
309 575-583 Chemical denotes curcumin MESH:D003474
310 823-831 Chemical denotes curcumin MESH:D003474
311 935-943 Chemical denotes hydrogen MESH:D006859
312 1076-1084 Chemical denotes curcumin MESH:D003474
313 1168-1176 Chemical denotes hydrogen MESH:D006859
328 1672-1677 Gene denotes Spike Gene:43740568
329 1463-1468 Gene denotes Spike Gene:43740568
330 1335-1340 Gene denotes Spike Gene:43740568
331 1283-1288 Gene denotes spike Gene:43740568
332 1274-1282 Species denotes SARS-CoV Tax:694009
333 1326-1334 Species denotes SARS-CoV Tax:694009
334 1454-1462 Species denotes SARS-CoV Tax:694009
335 1558-1566 Species denotes SARS-CoV Tax:694009
336 1663-1671 Species denotes SARS-CoV Tax:694009
337 1567-1572 Gene denotes Spike Gene:43740568
338 1248-1270 Chemical denotes Bis-demethoxy curcumin MESH:C034786
339 1403-1425 Chemical denotes Bis-demethoxy curcumin MESH:C034786
340 1530-1552 Chemical denotes Bis-demethoxy curcumin MESH:C034786
341 1635-1657 Chemical denotes Bis-demethoxy curcumin MESH:C034786
345 1769-1774 Gene denotes Spike Gene:43740568
346 1760-1768 Species denotes SARS-CoV Tax:694009
347 1726-1734 Chemical denotes curcumin MESH:D003474
351 3163-3173 Species denotes SARS-CoV-2 Tax:2697049
352 3174-3179 Gene denotes Spike Gene:43740568
353 3129-3137 Chemical denotes curcumin MESH:D003474
390 4536-4541 Gene denotes ARG99 Gene:83857
391 4875-4880 Gene denotes ARG99 Gene:83857
392 4543-4549 Chemical denotes GLY100
393 4551-4554 Chemical denotes TRP MESH:D014364
394 4560-4566 Chemical denotes ILE116
395 4568-4574 Chemical denotes ILE117
396 4576-4582 Chemical denotes ASN118
397 4584-4590 Chemical denotes VAL123
398 4592-4598 Chemical denotes MET144
399 4600-4606 Chemical denotes SER165
400 4608-4614 Chemical denotes ASP166
401 4616-4622 Chemical denotes PHE168
402 4624-4630 Chemical denotes ARG183
403 4632-4638 Chemical denotes PHE185
404 4640-4646 Chemical denotes LYS198
405 4648-4654 Chemical denotes ILE219
406 4656-4662 Chemical denotes PHE220
407 4702-4710 Chemical denotes hydrogen MESH:D006859
408 4779-4787 Chemical denotes curcumin MESH:D003474
409 4824-4832 Chemical denotes curcumin MESH:D003474
410 4853-4861 Chemical denotes hydrogen MESH:D006859
411 4882-4888 Chemical denotes MET144
412 4890-4896 Chemical denotes LYS198
413 5027-5033 Chemical denotes ASP166
414 5035-5041 Chemical denotes VAL123
415 5043-5049 Chemical denotes PHE185
416 5085-5091 Chemical denotes GLY100
417 5093-5096 Chemical denotes TRP MESH:D014364
418 5102-5108 Chemical denotes ILE117
419 5110-5116 Chemical denotes ASN118
420 5118-5124 Chemical denotes ARG183
421 5126-5132 Chemical denotes ILE116
422 5134-5140 Chemical denotes PHE168
423 5142-5148 Chemical denotes SER165
424 5150-5156 Chemical denotes PHE220
425 5158-5164 Chemical denotes ILE219
457 5234-5239 Gene denotes spike Gene:43740568
458 5251-5261 Species denotes SARS-CoV-2 Tax:2697049
459 5199-5207 Chemical denotes hydrogen MESH:D006859
460 5276-5315 Chemical denotes 3-5-di-tert-butyl-4-hydroxybenzaldehyde MESH:C513957
461 5316-5324 Chemical denotes curcumin MESH:D003474
462 5344-5350 Chemical denotes ARG355
463 5352-5358 Chemical denotes TYR396
464 5360-5366 Chemical denotes PRO426
465 5368-5374 Chemical denotes ASP428
466 5376-5382 Chemical denotes THR430
467 5392-5398 Chemical denotes PHE429
468 5400-5403 Chemical denotes PHE MESH:D010649
469 5409-5415 Chemical denotes GLU516
470 5417-5423 Chemical denotes SER514
471 5425-5431 Chemical denotes LEU517
472 5436-5442 Chemical denotes PHE515
473 5482-5490 Chemical denotes hydrogen MESH:D006859
474 5557-5565 Chemical denotes curcumin MESH:D003474
475 5602-5610 Chemical denotes curcumin MESH:D003474
476 5629-5637 Chemical denotes hydrogen MESH:D006859
477 5651-5657 Chemical denotes ARG355
478 5659-5665 Chemical denotes LEU517
479 5670-5676 Chemical denotes THR430
480 5797-5803 Chemical denotes PHE464
481 5813-5819 Chemical denotes GLU516
482 5821-5827 Chemical denotes SER514
483 5829-5835 Chemical denotes PHE515
484 5837-5843 Chemical denotes TYR396
485 5845-5851 Chemical denotes PRO426
486 5853-5859 Chemical denotes ASP428
487 5864-5870 Chemical denotes PHE429
496 6192-6197 Gene denotes Spike Gene:43740568
497 6221-6226 Gene denotes Spike Gene:43740568
498 6183-6191 Species denotes SARS-CoV Tax:694009
499 6210-6220 Species denotes SARS-CoV-2 Tax:2697049
500 5876-5884 Chemical denotes curcumin MESH:D003474
501 5931-5952 Chemical denotes Bis-demethoxycurcumin MESH:C034786
502 6044-6052 Chemical denotes curcumin MESH:D003474
503 6156-6177 Chemical denotes Bis-demethoxycurcumin MESH:C034786
519 6427-6432 Gene denotes spike Gene:43740568
520 6456-6460 Gene denotes ACE2 Gene:59272
521 6561-6566 Gene denotes spike Gene:43740568
522 6688-6693 Gene denotes spike Gene:43740568
523 6798-6803 Gene denotes spike Gene:43740568
524 6339-6349 Species denotes SARS-CoV-2 Tax:2697049
525 6416-6426 Species denotes SARS-CoV-2 Tax:2697049
526 6582-6592 Species denotes SARS-CoV-2 Tax:2697049
527 6677-6687 Species denotes SARS-CoV-2 Tax:2697049
528 6787-6797 Species denotes SARS-CoV-2 Tax:2697049
529 6350-6355 Gene denotes spike Gene:43740568
530 6313-6335 Chemical denotes Bis-demethoxy curcumin MESH:C034786
531 6511-6533 Chemical denotes Bis-demethoxy curcumin MESH:C034786
532 6641-6663 Chemical denotes Bis-demethoxy curcumin MESH:C034786
533 6759-6781 Chemical denotes Bis-demethoxy curcumin MESH:C034786
543 7169-7177 Chemical denotes Curcumin MESH:D003474
544 7472-7518 Chemical denotes 5-di-tert-butyl-4-hydroxybenzaldehyde curcumin
545 7520-7524 Chemical denotes BHBC
546 7527-7553 Chemical denotes 4-methoxy-1-naphthaldehyde
547 7554-7562 Chemical denotes curcumin MESH:D003474
548 7564-7567 Chemical denotes MNC
549 7570-7593 Chemical denotes Syringaldehyde curcumin
550 7722-7730 Chemical denotes hydrogen MESH:D006859
551 7769-7772 Disease denotes HBD MESH:C564145
553 7905-7913 Chemical denotes curcumin MESH:D003474
557 7993-7997 Chemical denotes BHBC
558 8070-8074 Chemical denotes BDMC
559 7959-7962 Disease denotes HBD MESH:C564145
581 8941-8948 Chemical denotes octanol MESH:D000442
582 8949-8954 Chemical denotes water MESH:D014867
583 9013-9021 Chemical denotes hydrogen MESH:D006859
584 9053-9061 Chemical denotes hydrogen MESH:D006859
585 9121-9125 Chemical denotes BHBC
586 9127-9166 Chemical denotes 3-5-di-tert-butyl-4-hydroxybenzaldehyde MESH:C513957
587 9167-9175 Chemical denotes curcumin MESH:D003474
588 9177-9180 Chemical denotes MNC
589 9182-9208 Chemical denotes 4-methoxy-1-naphthaldehyde
590 9209-9217 Chemical denotes curcumin MESH:D003474
591 9219-9223 Chemical denotes BDMC
592 9225-9247 Chemical denotes Bis-demethoxy curcumin MESH:C034786
593 9254-9272 Chemical denotes Demethoxy curcumin MESH:C050229
594 9279-9291 Chemical denotes Ferulic-acid MESH:C004999
595 9292-9300 Chemical denotes curcumin MESH:D003474
596 9302-9305 Chemical denotes IBC MESH:D002015
597 9307-9325 Chemical denotes Ibuprofen curcumin
598 9332-9352 Chemical denotes Isovanillin curcumin
599 9359-9373 Chemical denotes Syringaldehyde MESH:C069665
600 9374-9382 Chemical denotes curcumin MESH:D003474
601 9037-9040 Disease denotes HBD MESH:C564145
625 10157-10171 Gene denotes P-glycoprotein Gene:5243
626 10178-10192 Gene denotes P-glycoprotein Gene:5243
627 10518-10524 Gene denotes CYP3A4 Gene:1576
628 10538-10572 Gene denotes compounds-8, -11, -14, -15 and -16
629 10630-10636 Gene denotes CYP2C9 Gene:1559
630 10734-10752 Gene denotes (compound-1 and -4
631 10865-10869 Gene denotes OCT2 Gene:6582
632 9415-9420 Chemical denotes ADMET
633 9579-9587 Chemical denotes curcumin MESH:D003474
634 9624-9629 Chemical denotes water MESH:D014867
635 9671-9675 Chemical denotes BHBC
636 9731-9737 Chemical denotes Caco-2
637 9787-9791 Chemical denotes BHBC
638 10015-10023 Chemical denotes curcumin MESH:D003474
639 10109-10117 Chemical denotes curcumin MESH:D003474
640 10214-10218 Chemical denotes BHBC
641 10241-10263 Chemical denotes Ferrulic acid curcumin
642 10343-10351 Chemical denotes curcumin MESH:D003474
643 10428-10448 Chemical denotes Isovanillin curcumin
644 10450-10453 Chemical denotes IVC
645 10532-10536 Chemical denotes BHBC
646 10642-10650 Chemical denotes curcumin MESH:D003474
647 10804-10812 Chemical denotes curcumin MESH:D003474
649 11040-11048 Chemical denotes curcumin MESH:D003474
653 11187-11191 Chemical denotes BHBC
654 11361-11365 Chemical denotes BDMC
655 11097-11132 Disease denotes Metabolism Excretion   WS CP IA MESH:D018980
683 13363-13377 Gene denotes P-glycoprotein Gene:5243
684 13568-13574 Gene denotes CYP3A4 Gene:1576
685 13591-13597 Gene denotes CYP2C9 Gene:1559
686 13653-13657 Gene denotes OCT2 Gene:6582
687 13659-13687 Gene denotes organic cation transporter 2 Gene:6582
688 13286-13291 Species denotes Human Tax:9606
689 13391-13395 Species denotes PI-2 Tax:1214577
690 13428-13433 Species denotes Human Tax:9606
691 13489-13494 Species denotes human Tax:9606
692 13396-13410 Gene denotes P-glycoprotein Gene:5243
693 13206-13211 Chemical denotes Water MESH:D014867
694 13700-13704 Chemical denotes BHBC
695 13706-13745 Chemical denotes 3-5-di-tert-butyl-4-hydroxybenzaldehyde MESH:C513957
696 13746-13754 Chemical denotes curcumin MESH:D003474
697 13756-13759 Chemical denotes MNC
698 13761-13787 Chemical denotes 4-methoxy-1-naphthaldehyde
699 13788-13796 Chemical denotes curcumin MESH:D003474
700 13798-13802 Chemical denotes BDMC
701 13804-13826 Chemical denotes Bis-demethoxy curcumin MESH:C034786
702 13833-13851 Chemical denotes Demethoxy curcumin MESH:C050229
703 13858-13870 Chemical denotes Ferulic-acid MESH:C004999
704 13871-13879 Chemical denotes curcumin MESH:D003474
705 13881-13884 Chemical denotes IBC MESH:D002015
706 13886-13904 Chemical denotes Ibuprofen curcumin
707 13911-13931 Chemical denotes Isovanillin curcumin
708 13938-13952 Chemical denotes Syringaldehyde MESH:C069665
709 13953-13961 Chemical denotes curcumin MESH:D003474