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Human Metabolome Database Version 3.5

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Showing metabocard for Delta 8,14 -Sterol (HMDB06928)

Record Information
Version 3.5
Creation Date 2008-09-05 09:29:19 -0600
Update Date 2013-05-13 15:57:57 -0600
HMDB ID HMDB06928
Secondary Accession Numbers
  • HMDB06844
  • HMDB11607
Metabolite Identification
Common Name Delta 8,14 -Sterol
Description Delta 8,14 -Sterol is an intermediate in the biosynthesis of steroids (KEGG ID C11508), and is converted from O butusifoliol via the enzyme cytochrome P450, family 51, subfamily A (sterol 14-demethylase) [EC:1.14.13.70]. It is then converted to 4-alpha-methylfecosterol via the enzyme delta14-sterol reductase [EC:1.3.1.70].
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 4-alpha-Methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol
  2. 4a-Methyl-5a-ergosta-8,14,24(28)-trien-3b-ol
  3. 4a-Methylergosta-8,14,24(241)-trien-3b-ol
  4. 4alpha-Methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol
  5. delta 8,14 -Sterol
Chemical Formula C29H46O
Average Molecular Weight 410.6749
Monoisotopic Molecular Weight 410.354866094
IUPAC Name (2S,5S,6S,7S,14R,15R)-2,6,15-trimethyl-14-[(2R)-6-methyl-5-methylideneheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol
Traditional IUPAC Name delta 8,14 -sterol
CAS Registry Number 74635-33-9
SMILES [H][C@@]1(CC=C2C3=C(CC[C@]12C)[C@@]1(C)CC[C@H](O)[C@@H](C)[C@]1([H])CC3)[C@H](C)CCC(=C)C(C)C
InChI Identifier InChI=1S/C29H46O/c1-18(2)19(3)8-9-20(4)23-12-13-25-22-10-11-24-21(5)27(30)15-17-29(24,7)26(22)14-16-28(23,25)6/h13,18,20-21,23-24,27,30H,3,8-12,14-17H2,1-2,4-7H3/t20-,21+,23-,24+,27+,28-,29+/m1/s1
InChI Key HLAWVOWADPNAGN-BAHZUFOISA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Ergosterols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Triterpenes
  • a steroid(Cyc)
Substituents
  • 3 Hydroxy Steroid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Isoprene
  • Secondary Alcohol
Direct Parent Ergosterols and Derivatives
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0016 g/L ALOGPS
LogP 7.00 ALOGPS
LogP 6.97 ChemAxon
LogS -5.42 ALOGPS
pKa (strongest acidic) 18.96 ChemAxon
pKa (strongest basic) -1.1 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 20.23 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 130 ChemAxon
Polarizability 53.07 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB011216
KNApSAcK ID C00007523 Link_out
Chemspider ID 391501 Link_out
KEGG Compound ID C11508 Link_out
BioCyc ID CPD-9523 Link_out
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06928 Link_out
Metagene Link HMDB06928 Link_out
METLIN ID Not Available
PubChem Compound 443237 Link_out
PDB ID Not Available
ChEBI ID 30109 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Delta(14)-sterol reductase
Reactions:
  • 4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol + NADP+ = 4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + NADPH + H+ [RN:R05639]
Gene Name: TM7SF2
Uniprot ID: O76062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lanosterol 14-alpha demethylase
Reactions:
  • obtusifoliol + 3 O2 + 3 NADPH + 3 H+ = 4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + 3 NADP+ + 4 H2O [RN:R05731]
Gene Name: CYP51A1
Uniprot ID: Q16850 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA