Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for 5-Dehydroavenasterol (HMDB06852)

Record Information
Version 3.5
Creation Date 2008-08-13 07:49:58 -0600
Update Date 2013-02-08 17:15:26 -0700
HMDB ID HMDB06852
Secondary Accession Numbers None
Metabolite Identification
Common Name 5-Dehydroavenasterol
Description 5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids (KEGG ID C15783). It is the third to last step in the synthesis of Stigmasterol and is converted from delta 7-Avenasterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. It is then converted to Isofucosterol via the enzyme 7-dehydrocholesterol reductase [EC:1.3.1.21].
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
    Chemical Formula C29H46O
    Average Molecular Weight 410.6749
    Monoisotopic Molecular Weight 410.354866094
    IUPAC Name (2R,5S,15R)-2,15-dimethyl-14-[(2R,5Z)-5-(propan-2-yl)hept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
    Traditional IUPAC Name (2R,5S,15R)-14-[(2R,5Z)-5-isopropylhept-5-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
    CAS Registry Number Not Available
    SMILES C\C=C(/C(C)C)CC[C@@H](C)C1CCC2C3=CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
    InChI Identifier InChI=1S/C29H46O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,10-11,19-20,23,25-27,30H,8-9,12-18H2,1-6H3/b21-7-/t20-,23+,25?,26?,27?,28+,29-/m1/s1
    InChI Key XPRWWANUPMYKMF-UUHDPGOWSA-N
    Chemical Taxonomy
    Kingdom Organic Compounds
    Super Class Lipids
    Class Steroids and Steroid Derivatives
    Sub Class Stigmastanes and Derivatives
    Other Descriptors
    • Aliphatic Homopolycyclic Compounds
    • Triterpenes
    Substituents
    • 3 Hydroxy Steroid
    • Bicyclohexane
    • Cyclic Alcohol
    • Cyclohexane
    • Isoprene
    • Secondary Alcohol
    Direct Parent Stigmastanes 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 2.620E-04 g/L ALOGPS
    LogP 8.24 ALOGPS
    LogP 7.03 ChemAxon
    LogS -6.20 ALOGPS
    pKa (strongest acidic) 18.27 ChemAxon
    pKa (strongest basic) -1.4 ChemAxon
    Hydrogen Acceptor Count 1 ChemAxon
    Hydrogen Donor Count 1 ChemAxon
    Polar Surface Area 20.23 A2 ChemAxon
    Rotatable Bond Count 5 ChemAxon
    Refractivity 131.47 ChemAxon
    Polarizability 51.98 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 FDB024118
    KNApSAcK ID Not Available
    Chemspider ID Not Available
    KEGG Compound ID C15783 Link_out
    BioCyc ID CPD-4126 Link_out
    BiGG ID Not Available
    Wikipedia Link Not Available
    NuGOwiki Link HMDB06852 Link_out
    Metagene Link HMDB06852 Link_out
    METLIN ID Not Available
    PubChem Compound 23724575 Link_out
    PDB ID Not Available
    ChEBI ID Not Available
    References
    Synthesis Reference Not Available
    Material Safety Data Sheet (MSDS) Not Available
    General References Not Available
    Enzymes
    Name: Lathosterol oxidase
    Reactions:
    • 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 = cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O [RN:R03310 R07215]
    Gene Name: SC5DL
    Uniprot ID: O75845 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 7-dehydrocholesterol reductase
    Reactions:
    • cholesterol + NADP+ = cholesta-5,7-dien-3beta-ol + NADPH + H+ [RN:R01456]
    Gene Name: DHCR7
    Uniprot ID: Q9UBM7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA