Cocarboxylase

Identification

Name
Cocarboxylase
Accession Number
DB01987  (EXPT03031, EXPT03093)
Type
Small Molecule
Groups
Approved, Experimental
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.

Structure
Thumb
Synonyms
  • Thiamine diphosphate
  • Thiamine pyrophosphate
Product Ingredients
IngredientUNIICASInChI Key
Cocarboxylase chlorideXMK8K8EVIU154-87-0YXVCLPJQTZXJLH-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
EnBrace HRCocarboxylase (25 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Cobamamide (50 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic Acid (1 mg/1) + Glycine betaine (500 ug/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (5.23 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal Phosphate (25 ug/1) + Magnesium L-threonate (1 mg/1) + Magnesium ascorbate (24 mg/1) + Zinc ascorbate (1 mg/1)Capsule, delayed release pelletsOralJaymac Pharmaceuticals, Llc2015-04-08Not applicableUs
EnLyteCocarboxylase (25 ug/1) + 1,2-docosahexanoyl-sn-glycero-3-phosphoserine calcium (6.4 mg/1) + 1,2-icosapentoyl-sn-glycero-3-phosphoserine calcium (800 ug/1) + Citric acid monohydrate (1.83 mg/1) + Cobamamide (50 ug/1) + Ferrous cysteine glycinate (13.6 mg/1) + Flavin adenine dinucleotide (25 ug/1) + Folic Acid (1 mg/1) + Glycine betaine (500 ug/1) + Leucovorin (2.5 mg/1) + Levomefolate magnesium (7 mg/1) + NADH (25 ug/1) + Phosphatidyl serine (12 mg/1) + Pyridoxal Phosphate (25 ug/1) + Sodium Citrate (3.67 mg/1) + Magnesium L-threonate (1 mg/1) + Magnesium ascorbate (24 mg/1) + Zinc ascorbate (1 mg/1)Capsule, delayed release pelletsOralJaymac Pharmaceuticals Llc2011-10-01Not applicableUs
Categories
Not Available
UNII
Q57971654Y
CAS number
136-08-3
Weight
Average: 424.306
Monoisotopic: 424.037142664
Chemical Formula
C12H18N4O7P2S
InChI Key
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[[email protected]](O)(=O)O[[email protected]](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UBenzoylformate decarboxylaseNot AvailablePseudomonas putida
UPyruvate oxidaseNot AvailableLactobacillus plantarum (strain ATCC BAA-793 / NCIMB 8826 / WCFS1)
UDNANot AvailableHuman
UAcetolactate synthase, catabolicNot AvailableKlebsiella pneumoniae
UPyruvate dehydrogenase E1 componentNot AvailableEscherichia coli (strain K12)
UPyruvate-flavodoxin oxidoreductaseNot AvailableDesulfovibrio africanus
UIndole-3-pyruvate decarboxylaseNot AvailableEnterobacter cloacae
UCarboxyethylarginine synthaseNot AvailableStreptomyces clavuligerus
UTransketolase 1Not AvailableEscherichia coli (strain K12)
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB62636
KEGG Compound
C00068
PubChem Compound
5431
PubChem Substance
46504577
ChemSpider
5238
ChEBI
45931
ChEMBL
CHEMBL1236235
HET
TDP
Wikipedia
Thiamine_pyrophosphate
PDB Entries
1dtw / 1l8a / 1mcz / 1ols / 1olu / 1olx / 1pyd / 1qs0 / 1u5b / 1umb
show 38 more

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Capsule, delayed release pelletsOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-03di-2590000000-3b56b15f83f1eb31bbd6

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Thiamine phosphates
Alternative Parents
Organic pyrophosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives / 4,5-disubstituted thiazoles / Imidolactams / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Organopnictogen compounds / Organooxygen compounds
show 3 more
Substituents
Thiamine-phosphate / Organic pyrophosphate / 4,5-disubstituted 1,3-thiazole / Aminopyrimidine / Monoalkyl phosphate / Organic phosphoric acid derivative / Phosphoric acid ester / Alkyl phosphate / Imidolactam / Azole
show 14 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
thiamine phosphate (CHEBI:45931)

Targets

Kind
Protein
Organism
Pseudomonas putida
Pharmacological action
Unknown
General Function
Thiamine pyrophosphate binding
Specific Function
Not Available
Gene Name
mdlC
Uniprot ID
P20906
Uniprot Name
Benzoylformate decarboxylase
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
Uniprot Name
Pyruvate oxidase
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
Uniprot Name
Acetolactate synthase, catabolic
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
Uniprot Name
Pyruvate dehydrogenase E1 component
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 ferre...
Gene Name
por
Uniprot ID
P94692
Uniprot Name
Pyruvate synthase
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
Uniprot Name
Indole-3-pyruvate decarboxylase
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-argini...
Gene Name
ceaS
Uniprot ID
Q9LCV9
Uniprot Name
N(2)-(2-carboxyethyl)arginine synthase
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 tran...
Gene Name
tktA
Uniprot ID
P27302
Uniprot Name
Transketolase 1
Molecular Weight
72211.14 Da

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 17:37