TOI

(1~{R},2~{S},5~{S},6~{S})-2-[(1~{S})-1-[3-[(4-azanylidene-2-methyl-1~{H}-pyrimidin-5-yl)methyl]-4-methyl-5-[2-[oxidanyl (phosphonooxy)phosphoryl]oxyethyl]-1,3-thiazol-3-ium-2-yl]-1,4-bis(oxidanyl)-4-oxidanylidene-butyl]-6-oxidanyl-5-(3-oxid anyl-3-oxidanylidene-prop-1-en-2-yl)oxy-cyclohex-3-ene-1-carboxylic acid

Created:	2015-11-17
Last modified:	2020-06-05

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2 entries where TOI is found as a standalone ligand

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Chemical Details
Formal Charge	1
Atom Count	84
Chiral Atom Count	5
Bond Count	86
Aromatic Bond Count	5

2D diagram of TOI

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Chemical Component Summary
Name	(1~{R},2~{S},5~{S},6~{S})-2-[(1~{S})-1-[3-[(4-azanylidene-2-methyl-1~{H}-pyrimidin-5-yl)methyl]-4-methyl-5-[2-[oxidanyl (phosphonooxy)phosphoryl]oxyethyl]-1,3-thiazol-3-ium-2-yl]-1,4-bis(oxidanyl)-4-oxidanylidene-butyl]-6-oxidanyl-5-(3-oxid anyl-3-oxidanylidene-prop-1-en-2-yl)oxy-cyclohex-3-ene-1-carboxylic acid
Synonyms	ThDP, decarboxylated 2-oxoglutarate and isochorismate adduct, covalent intermediate II
Systematic Name (OpenEye OEToolkits)	(1~{R},2~{S},5~{S},6~{S})-2-[(1~{S})-1-[3-[(4-azanylidene-2-methyl-1~{H}-pyrimidin-5-yl)methyl]-4-methyl-5-[2-[oxidanyl(phosphonooxy)phosphoryl]oxyethyl]-1,3-thiazol-3-ium-2-yl]-1,4-bis(oxidanyl)-4-oxidanylidene-butyl]-6-oxidanyl-5-(3-oxidanyl-3-oxidanylidene-prop-1-en-2-yl)oxy-cyclohex-3-ene-1-carboxylic acid
Formula	C₂₆ H₃₅ N₄ O₁₆ P₂ S
Molecular Weight	753.586
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	CACTVS	3.385	CC1=NC(=N)C(=CN1)C[n+]2c(C)c(CCO[P](O)(=O)O[P](O)(O)=O)sc2[C](O)(CCC(O)=O)[CH]3C=C[CH](OC(=C)C(O)=O)[CH](O)[CH]3C(O)=O
SMILES	OpenEye OEToolkits	2.0.4	Cc1c(sc([n+]1CC2=CNC(=NC2=N)C)C(CCC(=O)O)(C3C=CC(C(C3C(=O)O)O)OC(=C)C(=O)O)O)CCOP(=O)(O)OP(=O)(O)O
Canonical SMILES	CACTVS	3.385	CC1=NC(=N)C(=CN1)C[n+]2c(C)c(CCO[P](O)(=O)O[P](O)(O)=O)sc2[C@](O)(CCC(O)=O)[C@H]3C=C[C@H](OC(=C)C(O)=O)[C@@H](O)[C@@H]3C(O)=O
Canonical SMILES	OpenEye OEToolkits	2.0.4	[H]/N=C/1\C(=CNC(=N1)C)C[n+]2c(c(sc2[C@](CCC(=O)O)([C@H]3C=C[C@@H]([C@H]([C@@H]3C(=O)O)O)OC(=C)C(=O)O)O)CCOP(=O)(O)OP(=O)(O)O)C
InChI	InChI	1.03	InChI=1S/C26H34N4O16P2S/c1-12-18(7-9-44-48(42,43)46-47(39,40)41)49-25(30(12)11-15-10-28-14(3)29-22(15)27)26(38,8-6-19(31)32)16-4-5-17(45-13(2)23(34)35)21(33)20(16)24(36)37/h4-5,10,16-17,20-21,33,38H,2,6-9,11H2,1,3H3,(H7-,27,28,29,31,32,34,35,36,37,39,40,41,42,43)/p+1/t16-,17-,20+,21+,26-/m0/s1
InChIKey	InChI	1.03	AJVZCJMDQDMTBE-BLORIJLWSA-O

Related Resource References

Resource Name	Reference
PubChem	121225429

RCSB PDB Core Operations are funded by the U.S. National Science Foundation (DBI-2321666), the US Department of Energy (DE-SC0019749), and the National Cancer Institute, National Institute of Allergy and Infectious Diseases, and National Institute of General Medical Sciences of the National Institutes of Health under grant R01GM157729.