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Identification
NameThiamin Diphosphate
Accession NumberDB01987  (EXPT03031, EXPT03093)
TypeSmall Molecule
GroupsExperimental
Description

The coenzyme form of Vitamin B1 present in many animal tissues. It is a required intermediate in the pyruvate dehydrogenase complex and the ketoglutarate dehydrogenase complex. [PubChem]

Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIIXMK8K8EVIU
CAS number154-87-0
WeightAverage: 424.306
Monoisotopic: 424.037142664
Chemical FormulaC12H18N4O7P2S
InChI KeyInChIKey=AYEKOFBPNLCAJY-UHFFFAOYSA-N
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)
IUPAC Name
3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(hydrogen phosphonatooxy)(hydroxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
SMILES
CC1=C(CCO[P@](O)(=O)O[P@](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • Organic pyrophosphate
  • Monoalkyl phosphate
  • Aminopyrimidine
  • 4,5-disubstituted 1,3-thiazole
  • Imidolactam
  • Alkyl phosphate
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Organic salt
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9991
Blood Brain Barrier+0.9185
Caco-2 permeable-0.5574
P-glycoprotein substrateNon-substrate0.5425
P-glycoprotein inhibitor INon-inhibitor0.9236
P-glycoprotein inhibitor IINon-inhibitor0.9453
Renal organic cation transporterNon-inhibitor0.8564
CYP450 2C9 substrateNon-substrate0.8308
CYP450 2D6 substrateNon-substrate0.8148
CYP450 3A4 substrateNon-substrate0.6365
CYP450 1A2 substrateNon-inhibitor0.7333
CYP450 2C9 inhibitorNon-inhibitor0.7484
CYP450 2D6 inhibitorNon-inhibitor0.8677
CYP450 2C19 inhibitorNon-inhibitor0.7037
CYP450 3A4 inhibitorNon-inhibitor0.9729
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8603
Ames testNon AMES toxic0.6085
CarcinogenicityNon-carcinogens0.908
BiodegradationNot ready biodegradable0.7694
Rat acute toxicity2.6182 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8781
hERG inhibition (predictor II)Non-inhibitor0.5906
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.372 mg/mLALOGPS
logP-1.2ALOGPS
logP-5.8ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area171.8 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity94.02 m3·mol-1ChemAxon
Polarizability35.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
unknown
General Function:
Thiamine pyrophosphate binding
Specific Function:
Not Available
Gene Name:
mdlC
Uniprot ID:
P20906
Molecular Weight:
56354.475 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Lactobacillus plantarum (strain ATCC BAA-793 / NCIMB 8826 / WCFS1)
Pharmacological action
unknown
General Function:
Thiamine pyrophosphate binding
Specific Function:
Important for the aerobic growth. Decarboxylates pyruvate in four steps. The energy released is partially stored in acetyl phosphate.
Gene Name:
pox5
Uniprot ID:
P37063
Molecular Weight:
66110.5 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
3. DNA
Kind
Nucleotide
Organism
Human
Pharmacological action
unknown
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Klebsiella pneumoniae
Pharmacological action
unknown
General Function:
Thiamine pyrophosphate binding
Specific Function:
Not Available
Gene Name:
budB
Uniprot ID:
P27696
Molecular Weight:
60337.52 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Pyruvate dehydrogenase activity
Specific Function:
Component of the pyruvate dehydrogenase (PDH) complex, that catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2).
Gene Name:
aceE
Uniprot ID:
P0AFG8
Molecular Weight:
99667.78 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Desulfovibrio africanus
Pharmacological action
unknown
General Function:
Thiamine pyrophosphate binding
Specific Function:
Catalyzes the ferredoxin-dependent oxidative decarboxylation of pyruvate. Required for the transfer of electrons from pyruvate to ferredoxin (PubMed:9294422, PubMed:7612653). Ferredoxin I and ferredoxin II, which are single 4Fe-4S cluster ferredoxins are the most effective electron carriers of POR (PubMed:7612653).
Gene Name:
por
Uniprot ID:
P94692
Molecular Weight:
133679.405 Da
Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
unknown
General Function:
Thiamine pyrophosphate binding
Specific Function:
Not Available
Gene Name:
ipdC
Uniprot ID:
P23234
Molecular Weight:
60022.965 Da
Kind
Protein
Organism
Streptomyces clavuligerus
Pharmacological action
unknown
General Function:
Thiamine pyrophosphate binding
Specific Function:
Involved in the biosynthesis of the beta-lactamase inhibitor, clavulanic acid. Catalyzes the thiamine diphosphate (ThDP) dependent condensation of D-glyceraldehyde-3-phosphate (D-G3P) with L-arginine to yield the beta-amino acid, N2-(2-carboxyethyl)arginine (CEA) via a beta-elimination resulting in the formation of an enol which undergoes a second elimination to generate the alpha,beta-unsatura...
Gene Name:
ceaS
Uniprot ID:
Q9LCV9
Molecular Weight:
60906.59 Da
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Transketolase activity
Specific Function:
Catalyzes the reversible transfer of a two-carbon ketol group from sedoheptulose-7-phosphate to glyceraldehyde-3-phosphate, producing xylulose-5-phosphate and ribose-5-phosphate. Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:
tktA
Uniprot ID:
P27302
Molecular Weight:
72211.14 Da
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23