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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-08-13 11:06:51 UTC
Update Date2020-02-26 21:26:49 UTC
HMDB IDHMDB0006840
Secondary Accession Numbers
  • HMDB06840
Metabolite Identification
Common Name4,4-Dimethyl-5a-cholesta-8-en-3b-ol
DescriptionTetrahydrofolyl-[Glu](n), also known as THF-L-glutamic acid or THF-polyglutamate, belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) . Tetrahydrofolyl-[Glu](n) is a strong basic compound (based on its pKa). Within humans, tetrahydrofolyl-[glu](N) participates in a number of enzymatic reactions. In particular, tetrahydrofolyl-[glu](N) can be biosynthesized from tetrahydrofolyl-[glu](2) and L-glutamic acid; which is mediated by the enzyme folylpolyglutamate synthase. In addition, tetrahydrofolyl-[glu](N) can be converted into tetrahydrofolyl-[glu](2) and L-glutamic acid through its interaction with the enzyme Gamma-glutamyl hydrolase. In humans, tetrahydrofolyl-[glu](N) is involved in the metabolic disorder called the methylenetetrahydrofolate reductase deficiency (mthfrd) pathway. Sample structure image shows the case when n=3.
Structure
Data?1582752409
Synonyms
ValueSource
Tetrahydrofolyl-[glu](n+1)HMDB
Tetrahydropteroyl-[gamma-glu]NHMDB
Tetrahydropteroyl-[gamma-glu]n+1HMDB
THF-L-Glutamic acidHMDB
THF-PolyglutamateHMDB
3beta-Hydroxy-4,4-dimethyl-8(9)-cholesteneHMDB
3beta-Hydroxy-4,4-dimethylcholest-8(9)-eneHMDB
4,4-Dimethyl-3beta-hydroxy-8(9)-cholesteneHMDB
4,4-Dimethyl-3beta-hydroxycholest-8(9)-eneHMDB
4,4-Dimethyl-5alpha-cholesta-8-en-3beta-olHMDB
4,4-Dimethylcholest-8(9)-en-3beta-olHMDB
4,4-Dimethylcholesta-8(9)-en-3beta-olHMDB
Chemical FormulaC29H50O
Average Molecular Weight414.7067
Monoisotopic Molecular Weight414.386166222
IUPAC Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
Traditional Name(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-ol
CAS Registry NumberNot Available
SMILES
[H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)[C@]1([H])CC3
InChI Identifier
InChI=1S/C29H50O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h19-20,22-23,25-26,30H,8-18H2,1-7H3/t20-,22-,23?,25+,26+,28-,29-/m1/s1
InChI KeyFYHRVINOXYETMN-HFPXORMNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydrofolic acids and derivatives. These are heterocyclic compounds based on the 5,6,7,8-tetrahydropteroic acid skeleton conjugated with at least one L-glutamic acid unit (or a derivative thereof) .
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentTetrahydrofolic acids and derivatives
Alternative Parents
Substituents
  • Tetrahydrofolic acid or derivatives
  • Alpha-oligopeptide
  • Gamma-glutamyl alpha-amino acid
  • Glutamic acid or derivatives
  • Glutamine or derivatives
  • Tetracarboxylic acid or derivatives
  • Hippuric acid or derivatives
  • Hippuric acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-alpha-amino acid
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Alpha-amino acid or derivatives
  • Benzoic acid or derivatives
  • Benzamide
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Benzoyl
  • Aminopyrimidine
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • N-acyl-amine
  • Pyrimidine
  • Fatty acyl
  • Monocyclic benzene moiety
  • Fatty amide
  • Benzenoid
  • Vinylogous amide
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid
  • Carboxylic acid derivative
  • Azacycle
  • Secondary amine
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility0.00015 g/LALOGPS
logP7.16ALOGPS
logP7.81ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)19.55ChemAxon
pKa (Strongest Basic)-0.81ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity129.22 m³·mol⁻¹ChemAxon
Polarizability53.69 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pa-1009000000-a33746936424d40177c0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-3003900000-9e0d5f3612356977101cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0009500000-485fd160c5195d04d4d4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mt-4029100000-580315d3fda0dfb48c7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a70-4229000000-7d9d791bb7b2786a3c80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0001900000-158617c2e43f1a46b58aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0004900000-fdb687d0f9f704a35555Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000t-1009000000-fd10933f1f8d4206aeb3Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified<0.000121 uMNewborn (0-30 days old)Not Specified
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024106
KNApSAcK IDNot Available
Chemspider ID21231977
KEGG Compound IDC03541
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound45479706
PDB IDNot Available
ChEBI ID27650
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Energy production and conversion
Specific function:
Catalyzes the reduction of the delta-24 double bond of sterol intermediates. Protects cells from oxidative stress by reducing caspase 3 activity during apoptosis induced by oxidative stress. Also protects against amyloid-beta peptide-induced apoptosis.
Gene Name:
DHCR24
Uniprot ID:
Q15392
Molecular weight:
60100.805
Reactions
4,4-Dimethyl-5a-cholesta-8,24-dien-3-b-ol + NADPH + Hydrogen Ion → 4,4-Dimethyl-5a-cholesta-8-en-3b-ol + NADPdetails