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Human Metabolome Database Version 2.5

 

Showing metabocard for (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol (HMDB11644)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2009-02-02 11:59:47
Update Date 2009-05-05 21:07:38
Accession Number HMDB11644
Secondary Accession Numbers Not Available
Common Name (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol
Description (24R)-Cholest-5-ene-3-beta,7-alpha,24-triol is a hydroxysterol and a bile acid intermediate. It is produced from the reaction of 24(R)-Hydroxycholesterol with the enzyme CYP39A, which is also known as 24-hydroxycholesterol 7alpha-hydroxylase (EC 1.14.13.99). This enzyme catalyzes the following reaction: (24R)-cholest-5-ene-3beta,24-diol + NADPH + H+ O2 = (24R)-cholest-5-ene-3beta,7alpha,24-triol + NADP+ + H2O. This leads to the 7-alpha hydroxylation of 24(R)-hydroxycholesterol. This enzyme can act on both the 24R and 24S isomers.
Synonyms
  1. 5a-cholesta-7,24-dien-3-b-ol
  2. (24R)-cholest-5-ene 3-b,7-a,24-triol
  3. (24R)-cholest-5-ene-3beta,7alpha,24-triol
  4. 5a-cholesta-7,24-dien-3-beta-ol
Chemical IUPAC Name Not Available
Chemical Formula C27H46O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
—
Class
—
Sub Class
—
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 418.652
Monoisotopic Molecular Weight 418.344696
Isomeric SMILES CC(C)[C@H](O)CC[C@@H](C)C1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC(C)C(O)CCC(C)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID Not Available
BioCyc ID 5-ALPHA-CHOLESTA-724-DIEN-3-BETA-OL Link Image
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB11644 Link Image
Metagene Link HMDB11644 Link Image
METLIN ID Not Available
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/C27H46O3/c1-16(2)23(29)9-6-17(3)20-7-8-21-25-22(11-13-27(20,21)5)26(4)12-10-19(28)14-18(26)15-24(25)30/h15-17,19-25,28-30H,6-14H2,1-5H3/t17-,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 8.49e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 4.28 [Predicted by ALOGPS] 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 Not Available
Not Available
Predicted 13C NMR Spectrum Not Available
Not Available
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
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. Cytochrome P450 39A1
Enzyme 1 [top]
Enzyme 1 ID 11444
Enzyme 1 Name Cytochrome P450 39A1
Enzyme 1 Synonyms
  1. 24-hydroxycholesterol 7-alpha- hydroxylase
  2. Oxysterol 7-alpha-hydroxylase
  3. hCYP39A1
Enzyme 1 Gene Name CYP39A1
Enzyme 1 Protein Sequence >Cytochrome P450 39A1 
MELISPTVIIILGCLALFLLLQRKNLRRPPCIKGWIPWIGVGFEFGKAPLEFIEKARIKY
GPIFTVFAMGNRMTFVTEEEGINVFLKSKKVDFELAVQNIVYRTASIPKNVFLALHEKLY
IMLKGKMGTVNLHQFTGQLTEELHEQLENLGTHGTMDLNNLVRHLLYPVTVNMLFNKSLF
STNKKKIKEFHQYFQVYDEDFEYGSQLPECLLRNWSKSKKWFLELFEKNIPDIKACKSAK
DNSMTLLQATLDIVETETSKENSPNYGLLLLWASLSNAVPVAFWTLAYVLSHPDIHKAIM
EGISSVFGKAGKDKIKVSEDDLENLLLIKWCVLETIRLKAPGVITRKVVKPVEILNYIIP
SGDLLMLSPFWLHRNPKYFPEPELFKPERWKKANLEKHSFLDCFMAFGSGKFQCPARWFA
LLEVQMCIILILYKYDCSLLDPLPKQSYLHLVGVPQPEGQCRIEYKQRI
Enzyme 1 Number of Residues 469
Enzyme 1 Molecular Weight 54116
Enzyme 1 Theoretical pI Not Available
Enzyme 1 GO Classification
Function
  • binding
  • catalytic activity
  • cation binding
  • heme binding
  • ion binding
  • iron ion binding
  • monooxygenase activity
  • oxidoreductase activity
  • tetrapyrrole binding
  • transition metal ion binding
Process
  • cellular metabolism
  • electron transport
  • generation of precursor metabolites and energy
  • metabolism
  • physiological process
Component
—
Enzyme 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Enzyme 1 Specific Function Involved in the bile acid metabolism. Has a preference for 24-hydroxycholesterol, and converts it into a 7-alpha- hydroxylated product
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions
  • H+ + Nicotinamide adenine dinucleotide phosphate - reduced + O2 + 24-Hydroxycholesterol --> H2O + Nicotinamide adenine dinucleotide phosphate + 7-alpha,24(S)-Dihydroxycholesterol
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 7533024 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q9NYL5 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name CP39A_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 AF237982 Link Image
Enzyme 1 GeneCard ID Not Available
Enzyme 1 GenAtlas ID CYP39A1 Link Image
Enzyme 1 HGNC ID HGNC:17449 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Li-Hawkins J, Lund EG, Bronson AD, Russell DW: Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol. J Biol Chem. 2000 Jun 2;275(22):16543-9. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available