3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate

C125H125BBr4F5N9O17 — CID 159342576

IUPAC3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
SMILESBrC1CCOCC1.CCC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(-c3cccc(OC4CCOCC4)c3F)cc12.COC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(-c3cccc(OC4CCOCC4)c3F)cc12.COC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(B(O)O)cc12.Fc1c(Br)cccc1OC1CCOCC1.Fc1c(Br)cccc1OC1CCOCC1.Oc1cccc(Br)c1F
InChIInChI=1S/C35H34FN3O3.C34H32FN3O4.C23H22BN3O4.2C11H12BrFO2.C6H4BrFO.C5H9BrO/c1-2-31(40)29-21-37-35(39(22-24-10-5-3-6-11-24)23-25-12-7-4-8-13-25)34-28(29)20-30(38-34)27-14-9-15-32(33(27)36)42-26-16-18-41-19-17-26;1-40-34(39)28-20-36-33(38(21-23-9-4-2-5-10-23)22-24-11-6-3-7-12-24)32-27(28)19-29(37-32)26-13-8-14-30(31(26)35)42-25-15-17-41-18-16-25;1-31-23(28)19-13-25-22(21-18(19)12-20(26-21)24(29)30)27(14-16-8-4-2-5-9-16)15-17-10-6-3-7-11-17;2*12-9-2-1-3-10(11(9)13)15-8-4-6-14-7-5-8;7-4-2-1-3-5(9)6(4)8;6-5-1-3-7-4-2-5/h3-15,20-21,26,38H,2,16-19,22-23H2,1H3;2-14,19-20,25,37H,15-18,21-22H2,1H3;2-13,26,29-30H,14-15H2,1H3;2*1-3,8H,4-7H2;1-3,9H;5H,1-4H2
InChIKeyLGHVAYVBOAVPIU-UHFFFAOYSA-N
MW2450.84 g/mol
LogP27.03
Rot. Bonds30

About 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate

3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate (PubChem CID 159342576) has the molecular formula C125H125BBr4F5N9O17 and a molecular weight of 2450.84 g/mol. Its IUPAC name is 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate.

Molecular Properties

Compound Name3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
PubChem CID159342576
Molecular FormulaC125H125BBr4F5N9O17
Molecular Weight2450.84 g/mol
Exact Mass2445.59
IUPAC Name3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
SMILESBrC1CCOCC1.CCC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(-c3cccc(OC4CCOCC4)c3F)cc12.COC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(-c3cccc(OC4CCOCC4)c3F)cc12.COC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(B(O)O)cc12.Fc1c(Br)cccc1OC1CCOCC1.Fc1c(Br)cccc1OC1CCOCC1.Oc1cccc(Br)c1F
InChIInChI=1S/C35H34FN3O3.C34H32FN3O4.C23H22BN3O4.2C11H12BrFO2.C6H4BrFO.C5H9BrO/c1-2-31(40)29-21-37-35(39(22-24-10-5-3-6-11-24)23-25-12-7-4-8-13-25)34-28(29)20-30(38-34)27-14-9-15-32(33(27)36)42-26-16-18-41-19-17-26;1-40-34(39)28-20-36-33(38(21-23-9-4-2-5-10-23)22-24-11-6-3-7-12-24)32-27(28)19-29(37-32)26-13-8-14-30(31(26)35)42-25-15-17-41-18-16-25;1-31-23(28)19-13-25-22(21-18(19)12-20(26-21)24(29)30)27(14-16-8-4-2-5-9-16)15-17-10-6-3-7-11-17;2*12-9-2-1-3-10(11(9)13)15-8-4-6-14-7-5-8;7-4-2-1-3-5(9)6(4)8;6-5-1-3-7-4-2-5/h3-15,20-21,26,38H,2,16-19,22-23H2,1H3;2-14,19-20,25,37H,15-18,21-22H2,1H3;2-13,26,29-30H,14-15H2,1H3;2*1-3,8H,4-7H2;1-3,9H;5H,1-4H2
InChIKeyLGHVAYVBOAVPIU-UHFFFAOYSA-N
XLogP27.03
TPSA309.19 Ų
H-Bond Donors6
H-Bond Acceptors23
Rotatable Bonds30
Heavy Atoms161
Complexity—

Lipinski Rule of Five

4 violations

RuleValue
MW ≤ 5002450.84
LogP ≤ 527.03
H-Bond Donors ≤ 56
H-Bond Acceptors ≤ 1023

Computed Properties (RDKit)

Structural Alerts{'alert_name': 'alkyl_halide', 'substructure': 'N/A'}, {'alert_name': 'heavy_metal', 'substructure': 'N/A'}

Analyze 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate with MolForge

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Related Compounds

CID 159389762
CID 159389762
bis(2-(4-bromo-3-methoxyphenyl)-1,4-dioxane);[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;(3-methoxyphenyl)boronic acid;2-(3-methoxyphenyl)-1,4-dioxane;methyl 7-(dibenzylamino)-2-[4-(1,4-dioxan-2-yl)-2-methoxyphenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 159026626
bis(6-bromo-5-fluoro-N,N-dimethylpyridine-3-carboxamide);6-bromo-5-fluoropyridine-3-carboxylic acid;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[5-(dimethylcarbamoyl)-3-fluoro-2-pyridinyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 159185553
(4-bromo-3-fluorophenyl)boronic acid;bis(2-(4-bromo-3-fluorophenyl)pyrazine);2-bromopyrazine;7-(dibenzylamino)-2-(2-fluoro-4-pyrazin-2-ylphenyl)-N-methyl-1H-pyrrolo[2,3-c]pyridine-4-carboxamide;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-(2-fluoro-4-pyrazin-2-ylphenyl)-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 159544893
2-amino-2-methylpropan-1-ol;3-bromo-2-fluorobenzoyl chloride;bis(2-(3-bromo-2-fluorophenyl)-4,4-dimethyl-5H-1,3-oxazole);1-[7-(dibenzylamino)-2-[3-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-2-fluorophenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[3-(4,4-dimethyl-5H-1,3-oxazol-2-yl)-2-fluorophenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 159867109
1-bromo-2-fluoro-3-nitrobenzene;bis(2-(3-bromo-2-fluorophenyl)oxolane);1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxolan-2-yl)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;2,3-dihydrofuran;2-(2-fluoro-3-nitrophenyl)-2,5-dihydrofuran;2-fluoro-3-(oxolan-2-yl)aniline;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxolan-2-yl)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 160364669
4-bromo-3-methoxybenzaldehyde;4-bromo-3-methoxybenzonitrile;bis(2-(4-bromo-3-methoxyphenyl)-1,4-dioxane);2-(4-bromo-3-methoxyphenyl)oxirane;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[4-(1,4-dioxan-2-yl)-2-methoxyphenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 160976664
4-bromo-3-fluorophenol;bis((2S)-2-[(4-bromo-3-fluorophenoxy)methyl]oxolane);[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-4-[[(2S)-oxolan-2-yl]methoxy]phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate;[(2S)-oxolan-2-yl]methanol
CID 161018321
2-(4-bromo-3-cyclopropyloxyphenyl)-1-methylimidazole;2-[2-cyclopropyloxy-4-(1-methylimidazol-2-yl)phenyl]-7-(dibenzylamino)-N-methyl-1H-pyrrolo[2,3-c]pyridine-4-carboxamide;2-[2-cyclopropyloxy-4-(1-methylimidazol-2-yl)phenyl]-7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 2-[2-cyclopropyloxy-4-(1-methylimidazol-2-yl)phenyl]-7-(dibenzylamino)-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 161082875
1-[3-bromo-1-(5-fluoropyrimidin-2-yl)pyrrolo[3,2-b]pyridin-6-yl]ethanone;3-[3-(difluoromethoxy)phenyl]-1-(5-fluoropyrimidin-2-yl)pyrrolo[3,2-b]pyridine-6-carboxylic acid;1-[3-[3-(difluoromethoxy)phenyl]-1-(5-fluoropyrimidin-2-yl)pyrrolo[3,2-b]pyridin-6-yl]ethanone;1-[1-(5-fluoropyrimidin-2-yl)pyrrolo[3,2-b]pyridin-6-yl]ethanone;1-(1H-pyrrolo[3,2-b]pyridin-6-yl)ethanone
CID 164045978
(4-bromo-3-fluorophenyl)boronic acid;bis(2-(4-bromo-3-fluorophenyl)pyrazine);2-bromopyrazine;7-(dibenzylamino)-2-(2-fluoro-4-pyrazin-2-ylphenyl)-1H-pyrrolo[2,3-c]pyridine-4-carboxylic acid;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-(2-fluoro-4-pyrazin-2-ylphenyl)-1H-pyrrolo[2,3-c]pyridine-4-carboxylate
CID 164949247

Frequently Asked Questions

What is the IUPAC name of 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate?
The IUPAC name of 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate (CID 159342576) is 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate.
What is the SMILES notation for 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate?
The canonical SMILES for 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate is BrC1CCOCC1.CCC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(-c3cccc(OC4CCOCC4)c3F)cc12.COC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(-c3cccc(OC4CCOCC4)c3F)cc12.COC(=O)c1cnc(N(Cc2ccccc2)Cc2ccccc2)c2[nH]c(B(O)O)cc12.Fc1c(Br)cccc1OC1CCOCC1.Fc1c(Br)cccc1OC1CCOCC1.Oc1cccc(Br)c1F.
What is the InChIKey of 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate?
The InChIKey is LGHVAYVBOAVPIU-UHFFFAOYSA-N. The full InChI is InChI=1S/C35H34FN3O3.C34H32FN3O4.C23H22BN3O4.2C11H12BrFO2.C6H4BrFO.C5H9BrO/c1-2-31(40)29-21-37-35(39(22-24-10-5-3-6-11-24)23-25-12-7-4-8-13-25)34-28(29)20-30(38-34)27-14-9-15-32(33(27)36)42-26-16-18-41-19-17-26;1-40-34(39)28-20-36-33(38(21-23-9-4-2-5-10-23)22-24-11-6-3-7-12-24)32-27(28)19-29(37-32)26-13-8-14-30(31(26)35)42-25-15-17-41-18-16-25;1-31-23(28)19-13-25-22(21-18(19)12-20(26-21)24(29)30)27(14-16-8-4-2-5-9-16)15-17-10-6-3-7-11-17;2*12-9-2-1-3-10(11(9)13)15-8-4-6-14-7-5-8;7-4-2-1-3-5(9)6(4)8;6-5-1-3-7-4-2-5/h3-15,20-21,26,38H,2,16-19,22-23H2,1H3;2-14,19-20,25,37H,15-18,21-22H2,1H3;2-13,26,29-30H,14-15H2,1H3;2*1-3,8H,4-7H2;1-3,9H;5H,1-4H2.
What are the key properties of 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate?
3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate has a molecular weight of 2450.84 g/mol, XLogP of 27.03, 30 rotatable bonds, 6 hydrogen bond donors, and 23 hydrogen bond acceptors.
Where does this data come from?
All data for 3-bromo-2-fluorophenol;bis(4-(3-bromo-2-fluorophenoxy)oxane);4-bromooxane;1-[7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridin-4-yl]propan-1-one;[7-(dibenzylamino)-4-methoxycarbonyl-1H-pyrrolo[2,3-c]pyridin-2-yl]boronic acid;methyl 7-(dibenzylamino)-2-[2-fluoro-3-(oxan-4-yloxy)phenyl]-1H-pyrrolo[2,3-c]pyridine-4-carboxylate is sourced from PubChem (CID 159342576), the world's largest open chemistry database maintained by the National Library of Medicine (NIH).