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Thiamine; O-Diphosphate 

AlkaPlorer ID: AK315929

Synonym: Thiamine diphosphate, Cocarboxylase, Diphosphothiamine, Pyruvodehydrase, Thiamine pyrophosphate, Aneurin diphosphate, Coxylase, Cozymase II, Interacton, Nutrase, Many other names

IUPAC Name: 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono phosphate

Structure

SMILES: CC1=NC=C(C[N+]2=CSC(CCOP(=O)([O-])OP(=O)(O)O)=C2C)C(=N)N1

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InChI: InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)

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InChIKey: AYEKOFBPNLCAJY-UHFFFAOYSA-N

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Properties Information

Molecule Weight: 424.31200000000007

TPSA？: 172.53

MolLogP？: 0.0401099999999996

Number of H-Donors: 4

Number of H-Acceptors: 8

RingCount: 2

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Homo sapiens Histone deacetylase 6 Inhibition -1.72 % 10.6019/CHEMBL4808148
Homo sapiens Histone deacetylase 6 Inhibition 37.77 % 10.6019/CHEMBL4808148
Homo sapiens Prelamin-A/C Potency 2818.4 nM None
Lactococcus lactis subsp. cremoris (strain MG1363) Thiamine transporter ThiT Kd 1.6 nM 10.1039/C7MD00079K
Photinus pyralis Luciferin 4-monooxygenase Potency 28695.4 nM None
Severe acute respiratory syndrome coronavirus 2 Replicase polyprotein 1ab Inhibition 8.63 % 10.6019/CHEMBL4495564
Severe acute respiratory syndrome coronavirus 2 SARS-CoV-2 Inhibition -0.13 % 10.6019/CHEMBL4495565

Metabolism Information

AKRT ID Reaction Reaction Link ID
AKRT000544 *NC(=O)CCCCC(S)CCSC(=O)C(C)C.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2c(C(O)C(C)C)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 MNXR183199
AKRT000545 *NC(=O)CCCCC(S)CCSC(=O)CC(C)C.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2c(C(O)CC(C)C)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 MNXR183200
AKRT000546 *NC(=O)CCCCC(S)CCSC(=O)CCC(=O)O.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2c(C(O)CCC(=O)O)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 MNXR179708
AKRT000547 *NC(=O)CCCCC(S)CCSC(=O)[C@@H](C)CC.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>CC[C@H](C)C(O)c1sc(CCOP(=O)(O)OP(=O)(O)O)c(C)[n+]1Cc1cnc(C)nc1N MNXR183201
AKRT002055 CC(=O)C(=O)O.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2c(C(C)O)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R00014
AKRT004481 CC(=O)[C@](C)(O)C(=O)O.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2c(C(C)O)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 RXN-14037
AKRT005357 CC(C)C(=O)C(=O)O.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2c(C(O)C(C)C)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R07599
AKRT005433 CC(C)CC(=O)C(=O)O.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2c(C(O)CC(C)C)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R07601
AKRT007087 CCC(=O)C(=O)O.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>CCC(O)c1sc(CCOP(=O)(O)OP(=O)(O)O)c(C)[n+]1Cc1cnc(C)nc1N R10996
AKRT007303 CCC(O)c1sc(CCOP(=O)(O)OP(=O)(O)O)c(C)[n+]1Cc1cnc(C)nc1N>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R10997
AKRT009882 CC[C@H](C)C(=O)C(=O)O.Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>CC[C@H](C)C(O)c1sc(CCOP(=O)(O)OP(=O)(O)O)c(C)[n+]1Cc1cnc(C)nc1N R07603
AKRT009900 CC[C@H](C)C(O)c1sc(CCOP(=O)(O)OP(=O)(O)O)c(C)[n+]1Cc1cnc(C)nc1N>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R07604
AKRT015382 Cc1ncc(C[n+]2c(C(C)O)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R00755
AKRT015384 Cc1ncc(C[n+]2c(C(O)C(C)C)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R07600
AKRT015387 Cc1ncc(C[n+]2c(C(O)CC(C)C)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R07602
AKRT015390 Cc1ncc(C[n+]2c(C(O)CCC(=O)O)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R03316
AKRT015414 Cc1ncc(C[n+]2csc(CCO)c2C)c(=N)[nH]1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1 enzymemap_48317
AKRT015437 Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 THIAMIN-PYROPHOSPHOKINASE-RXN
AKRT015444 Cc1ncc(C[n+]2csc(CCOP(=O)(O)O)c2C)c(=N)[nH]1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1 enzymemap_47974
AKRT015450 Cc1ncc(C[n+]2csc(CCOP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 THI-P-KIN-RXN
AKRT015452 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1>>Cc1ncc(C[n+]2csc(CCO)c2C)c(=N)[nH]1 enzymemap_55785
AKRT015453 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)O)c2C)c(=N)[nH]1 enzymemap_55236
AKRT015454 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1 enzymemap_47972
AKRT015455 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1.Nc1ncnc2c1ncn2[C@@H]1O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]1O>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)c2C)c(N)n1 RXN0-5291
AKRT015456 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1.O=C(O)CCC(=O)C(=O)O>>Cc1ncc(C[n+]2c(C(O)CCC(=O)O)sc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 R00621
AKRT015457 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCO)c2C)c(N)n1 enzymemap_55785
AKRT015458 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)O)c2C)c(N)n1 R00615
AKRT015459 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 THIAMIN-DIPHOSPHATE-KINASE-RXN
AKRT015460 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(=N)[nH]1 enzymemap_80283
AKRT015461 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)(O)O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 THIAMIN-TRIPHOSPHATASE-RXN
AKRT015462 Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@H]3O[C@@H](n4cnc5c(N)ncnc54)[C@H](O)[C@@H]3O)c2C)c(N)n1>>Cc1ncc(C[n+]2csc(CCOP(=O)(O)OP(=O)(O)O)c2C)c(N)n1 RXN0-5291