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Showing metabocard for 2-Methyl-1-hydroxypropyl-ThPP (HMDB0006866)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-08-13 17:09:17 UTC
Update Date2020-02-26 21:26:51 UTC
HMDB IDHMDB0006866
Secondary Accession Numbers
  • HMDB06866
Metabolite Identification
Common Name2-Methyl-1-hydroxypropyl-ThPP
Description2-Methyl-1-hydroxypropyl-ThPP is an intermediate in valine, leucine and isoleucine degradation(KEGG ID C15976). It is the second to last step in the synthesis of isobutyryl-CoA and is converted from 3-methyl-2-oxobutanoate via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]. It is then converted to S-(2-methylpropanoyl)-dihydrolipoamide-E via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]].
Structure
Data?1582752411
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hydroxy-2-methylpropyl-thiamine diphosphateChEBI
1-Hydroxy-2-methylpropyl-thiamine pyrophosphateChEBI
2-Methyl-1-hydroxypropyl-thiamine diphosphateChEBI
2-Methyl-1-hydroxypropyl-thiamine pyrophosphateChEBI
2-Methyl-1-hydroxypropyl-TPPChEBI
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-(2-diphosphoethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-iumChEBI
1-Hydroxy-2-methylpropyl-thiamine diphosphoric acidGenerator
1-Hydroxy-2-methylpropyl-thiamine pyrophosphoric acidGenerator
2-Methyl-1-hydroxypropyl-thiamine diphosphoric acidGenerator
2-Methyl-1-hydroxypropyl-thiamine pyrophosphoric acidGenerator
2-Methyl-1-hydroxypropyl-THPPChEBI
Chemical FormulaC16H27N4O8P2S
Average Molecular Weight497.42
Monoisotopic Molecular Weight497.102482574
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium
Traditional Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-2-methylpropyl)-4-methyl-1,3-thiazol-3-ium
CAS Registry NumberNot Available
SMILES
CC(C)C(O)C1=[N+](CC2=C(N)N=C(C)N=C2)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1
InChI Identifier
InChI=1S/C16H26N4O8P2S/c1-9(2)14(21)16-20(8-12-7-18-11(4)19-15(12)17)10(3)13(31-16)5-6-27-30(25,26)28-29(22,23)24/h7,9,14,21H,5-6,8H2,1-4H3,(H4-,17,18,19,22,23,24,25,26)/p+1
InChI KeySSYCSHKTIOHFEZ-UHFFFAOYSA-O
Chemical Taxonomy
Description 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
  • 2,4,5-trisubstituted 1,3-thiazole
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Heteroaromatic compound
  • Azole
  • Thiazole
  • Secondary alcohol
  • Azacycle
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Primary amine
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic alcohol
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.086 g/LALOGPS
logP-0.43ALOGPS
logP-6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area189.2 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity125.58 m³·mol⁻¹ChemAxon
Polarizability46.15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-9813800000-be6335483cae172e16a9Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-7911440000-4b658ddfc94358dd1ffaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xs-1368900000-1e4eff19f9ce5ce0973dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00xs-4419100000-89ecb98fc9c3156fe1c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-3941000000-528910db0245fc831976Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024122
KNApSAcK IDNot Available
Chemspider ID26333171
KEGG Compound IDC15976
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23724626
PDB IDNot Available
ChEBI ID48522
Food Biomarker OntologyNot Available
VMH ID2M1HPTPP
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
General function:
Involved in catalytic activity
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHB
Uniprot ID:
P21953
Molecular weight:
43122.065
Reactions
alpha-Ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxypropyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails
Enzyme Details
2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
General function:
Involved in oxidoreductase activity, acting on the aldehyde or oxo group of donors, disulfide as acceptor
Specific function:
The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:
BCKDHA
Uniprot ID:
P12694
Molecular weight:
50470.58
Reactions
alpha-Ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxidedetails
2-Methyl-1-hydroxypropyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails