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Human Metabolome Database Version 2.5

 

Showing metabocard for 27-Deoxy-5b-cyprinol (HMDB01231)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2005-11-16 15:48:42
Update Date 2009-06-23 13:49:03
Accession Number HMDB01231
Secondary Accession Numbers HMDB06264
Common Name 27-Deoxy-5b-cyprinol
Description 27-Deoxy-5b-cyprinol is an intermediate in Bile acid synthesis pathway, in a sequence of reactions catalyzed by sterol 27-hydroxylase (CYP27) in the oxidation of 5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol into 3 alpha,7 alpha,12 alpha-trihydroxy-5 beta-cholestanoic acid (PMID: 8496170). 5 beta-cholestane-3 alpha,7 alpha,12 alpha,25-tetrol 3-glucuronide, a metabolite of 27-Deoxy-5b-cyprinol, is the major bile alcohol component in serum from cerebrotendinous xanthomatosis patients (PMID: 7920441)
Synonyms
  1. 5-beta-cholestane-3-alpha-7-alpha-12-alpha-26-tetraol
  2. 5b-Cholestane-3a,7a,12a,26-tetrol
  3. 5-b-Cholestane-3a-7-tetraol
  4. 3a,7a,12a,26-Tetrahydroxy-5b-cholestane
  5. 5-beta-Cholestane-3a-7-tetraol
  6. (25R)-5-beta-cholestane-3-alpha,7-alpha,12-alpha,26-tetraol;5beta-cholestane-3alpha,7alpha,12alpha,27-tetraol
  7. 5beta-cholestane-3alpha,7alpha,12alpha,27-tetrol
  8. 5beta-cholestane-3alpha,7alpha,12alpha,27alpha-tetrol
Chemical IUPAC Name 17-(7-hydroxy-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triol
Chemical Formula C27H48O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Miscellaneous steroids
Family
  • Mammalian Metabolite
Species
  • primary alcohol
  • secondary alcohol
Biofunction
  • Hormones, Membrane component
Application
—
Source
  • Endogenous
Average Molecular Weight 436.668
Monoisotopic Molecular Weight 436.355255
Isomeric SMILES CC(CO)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4C[C@H](O)CC[C@]4(C)[C@H]3C[C@H](O)[C@]12C
Canonical SMILES CC(CO)CCCC(C)C1CCC2C3C(O)CC4CC(O)CCC4(C)C3CC(O)C12C
KEGG Compound ID Not Available
BioCyc ID 5-BETA-CHOLESTANE-3-ALPHA7-TETRAOL Link Image
BiGG ID 45828 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB01231 Link Image
Metagene Link HMDB01231 Link Image
METLIN ID 6095 Link Image
PubChem Compound 140 Link Image
PubChem Substance 6821725 Link Image
ChEBI ID Not Available
CAS Registry Number 862-53-3
InChI Identifier InChI=1/C27H48O4/c1-16(15-28)6-5-7-17(2)20-8-9-21-25-22(14-24(31)27(20,21)4)26(3)11-10-19(29)12-18(26)13-23(25)30/h16-25,28-31H,5-15H2,1-4H3/t16?,17-,18+,19-,20-,21+,22+,23?,24+,25+,26+,27-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0211 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.77 [Predicted by ALOGPS]; 5.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Membrane
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Bile Acid Biosynthesis SMP00035 Link Image map00120 Link Image
General References Not Available
Metabolic Enzymes
  1. cDNA FLJ76781, highly similar to Homo sapiens cytochrome P450, family 27, subfamily A, polypeptide 1
Enzyme 1 [top]
Enzyme 1 ID 13003
Enzyme 1 Name cDNA FLJ76781, highly similar to Homo sapiens cytochrome P450, family 27, subfamily A, polypeptide 1
Enzyme 1 Synonyms
  1. CYP27A1, mRNA
  2. Cytochrome P450, family 27, subfamily A, polypeptide 1, isoform CRA_b
Enzyme 1 Gene Name CYP27A1
Enzyme 1 Protein Sequence >cDNA FLJ76781, highly similar to Homo sapiens cytochrome P450, family 27, subfamily A, polypeptide 1 
MAALGCARLRWALRGAGRGLCPHGARAKAAIPAALPSDKATGAPGAGPGVRRRQRSLEEI
PRLGQLRFFFQLFVQGYALQLHQLQVLYKAKYGPMWMSYLGPQMHVNLASAPLLEQVMRQ
EGKYPVRNDMELWKEHRDQHDLTYGPFTTEGHHWYQLRQALNQRLLKPAEAALYTDAFNE
VIDDFMTRLDQLRAESASGNQVSDMAQLFYYFALEAICYILFEKRIGCLQRSIPEDTVTF
VRSIGLMFQNSLYATFLPKWTRPVLPFWKRYLDGWNAIFSFGKKLIDEKLEDMEAQLQAA
GPDGIQVSGYLHFLLASGQLSPREAMGSLPELLMAGVDTTSNTLTWALYHLSKDPEIQEA
LHEEVVGVVPAGQVPQHKDFAHMPLLKAVLKETLRLYPVVPTNSRIIEKEIEVDGFLFPK
NTQFVFCHYVVSRDPTAFSEPESFQPHRWLRNSQPATPRIQHPFGSVPFGYGVRACLGRR
IAELEMQLLLARLIQKYKVVLAPETGELKSVARIVLVPNKKVGLQFLQRQC
Enzyme 1 Number of Residues 531
Enzyme 1 Molecular Weight 60236
Enzyme 1 Theoretical pI 9.16
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 1 Specific Function Not Available
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function Not Available
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 158261859 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID A8K303 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name A8K303_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence Not Available
Enzyme 1 GenBank Gene ID AK290418 Link Image
Enzyme 1 GeneCard ID A8K303 Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available