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Record Information
Version3.6
Creation Date2008-08-13 17:09:17 UTC
Update Date2016-02-11 01:08:02 UTC
HMDB IDHMDB06866
Secondary Accession NumbersNone
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
Thumb
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
2-Methyl-1-hydroxypropylthiamine diphosphoric acidGenerator
1-Hydroxy-2-methylpropyl-thiamine pyrophosphoric acidGenerator
2-Methyl-1-hydroxypropyl-thiamine diphosphoric acidGenerator
2-Methyl-1-hydroxypropyl-thiamine pyrophosphoric acidGenerator
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 KeyInChIKey=SSYCSHKTIOHFEZ-UHFFFAOYSA-O
Chemical 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
  • 2,4,5-trisubstituted 1,3-thiazole
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Secondary alcohol
  • Azacycle
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity125.58 m3·mol-1ChemAxon
Polarizability46.15 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase DeficiencySMP00137Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase DeficiencySMP00138Not Available
3-hydroxyisobutyric acid dehydrogenase deficiencySMP00521Not Available
3-hydroxyisobutyric aciduriaSMP00522Not Available
3-Methylcrotonyl Coa Carboxylase Deficiency Type ISMP00237Not Available
3-Methylglutaconic Aciduria Type ISMP00139Not Available
3-Methylglutaconic Aciduria Type IIISMP00140Not Available
3-Methylglutaconic Aciduria Type IVSMP00141Not Available
Beta-Ketothiolase DeficiencySMP00173Not Available
Isobutyryl-coa dehydrogenase deficiencySMP00523Not Available
Isovaleric acidemiaSMP00524Not Available
Isovaleric AciduriaSMP00238Not Available
Maple Syrup Urine DiseaseSMP00199Not Available
Methylmalonate Semialdehyde Dehydrogenase DeficiencySMP00384Not Available
Methylmalonic AciduriaSMP00200Not Available
Propionic AcidemiaSMP00236Not Available
Valine, Leucine and Isoleucine DegradationSMP00032map00280
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024122
KNApSAcK IDNot Available
Chemspider ID26333171
KEGG Compound IDC15976
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB06866
Metagene LinkHMDB06866
METLIN IDNot Available
PubChem Compound23724626
PDB IDNot Available
ChEBI ID48522
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

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
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