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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-08-13 17:05:33 UTC
Update Date2021-09-14 15:45:46 UTC
HMDB IDHMDB0006865
Secondary Accession Numbers
  • HMDB0006946
  • HMDB06865
  • HMDB06946
Metabolite Identification
Common Name3-Methyl-1-hydroxybutyl-ThPP
Description3-Methyl-1-hydroxybutyl-ThPP 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. 3-Methyl-1-hydroxybutyl-ThPP exists in all living organisms, ranging from bacteria to humans. In humans, 3-methyl-1-hydroxybutyl-THPP is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway. 3-Methyl-1-hydroxybutyl-ThPP has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-methyl-1-hydroxybutyl-THPP a potential biomarker for the consumption of these foods. 3-Methyl-1-hydroxybutyl-ThPP is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 3-Methyl-1-hydroxybutyl-ThPP.
Structure
Data?1582752410
Synonyms
ValueSource
3-Methyl-1-hydroxybutyl-TPPKegg
Chemical FormulaC17H29N4O8P2S
Average Molecular Weight511.447
Monoisotopic Molecular Weight511.118132638
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxy-3-methylbutyl)-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-3-methylbutyl)-4-methyl-1,3-thiazol-3-ium
CAS Registry NumberNot Available
SMILES
CC(C)CC(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/C17H28N4O8P2S/c1-10(2)7-14(22)17-21(9-13-8-19-12(4)20-16(13)18)11(3)15(32-17)5-6-28-31(26,27)29-30(23,24)25/h8,10,14,22H,5-7,9H2,1-4H3,(H4-,18,19,20,23,24,25,26,27)/p+1
InChI KeyOZAWOYZVNPQFFO-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
Physiological effect

Adverse health effect

Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.077 g/LALOGPS
logP10(-0.29) g/LALOGPS
logP10(-5.7) g/LChemAxon
logS10(-3.8) g/LALOGPS
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 Count11ChemAxon
Refractivity130.25 m³·mol⁻¹ChemAxon
Polarizability48.36 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+215.91831661259
DarkChem[M-H]-209.89931661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#1CC1=NC=C(C[N+]2=C(C(CC(C)C)O[Si](C)(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N)=N13944.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#2CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)O)=C2C)C(N)=N13974.7Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#3CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C)=C2C)C(N)=N13959.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TMS,#4CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C)=N13976.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#1CC1=NC=C(C[N+]2=C(C(CC(C)C)O[Si](C)(C)C(C)(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N)=N14167.3Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#2CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)O)=C2C)C(N)=N14172.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#3CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O[Si](C)(C)C(C)(C)C)=C2C)C(N)=N14160.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
3-Methyl-1-hydroxybutyl-ThPP,1TBDMS,#4CC1=NC=C(C[N+]2=C(C(O)CC(C)C)SC(CCOP(=O)(O)OP(=O)(O)O)=C2C)C(N[Si](C)(C)C(C)(C)C)=N14178.8Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-8712900000-44639cddf5ac88be9b052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP GC-MS (1 TMS) - 70eV, Positivesplash10-014j-6262390000-db7a22cbb385f200f0fd2017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 10V, Positive-QTOFsplash10-01qi-1378940000-15be0e4fc27c59d8eb152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 20V, Positive-QTOFsplash10-0541-4309200000-c17630fd91cf03a198a92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 40V, Positive-QTOFsplash10-00dj-3952000000-1c97b66ad8638eecd4452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 10V, Positive-QTOFsplash10-03di-0200790000-01564e480d3ab339187c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 20V, Positive-QTOFsplash10-007k-1409710000-76598bfc6e49c4250a332021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Methyl-1-hydroxybutyl-ThPP 40V, Positive-QTOFsplash10-00di-3932000000-aa3b8e91eab38ba117e92021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
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 IDFDB024121
KNApSAcK IDNot Available
Chemspider ID22378483
KEGG Compound IDC15974
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23724625
PDB IDNot Available
ChEBI ID80220
Food Biomarker OntologyNot Available
VMH ID3M1HBTPP
MarkerDB IDNot Available
Good Scents IDNot Available
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
Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxidedetails
3-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(3-methylbutanoyl)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
Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxidedetails
3-Methyl-1-hydroxybutyl-ThPP + Enzyme N6-(lipoyl)lysine → [Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(3-methylbutanoyl)dihydrolipoyllysine + Thiamine pyrophosphatedetails