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Human Metabolome Database Version 2.5

 

Showing metabocard for 3 beta,7 alpha-Dihydroxy-5-cholestenoate (HMDB12454)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2009-07-13 13:46:54
Update Date 2009-07-27 15:23:59
Accession Number HMDB12454
Secondary Accession Numbers Not Available
Common Name 3 beta,7 alpha-Dihydroxy-5-cholestenoate
Description 3 beta,7 alpha-Dihydroxy-5-cholestenoate is found in the primary bile acid biosynthesis pathway. 3 beta,7 alpha-Dihydroxy-5-cholestenoate is created from 3 beta-Hydroxy-5-cholestenoate through the action of CYP7B (E1.14.13.100). 3 beta,7 alpha-Dihydroxy-5-cholestenoate is then converted to 7 alpha-Hydroxy-3-oxo-4-cholestenoate by the action of HSD3B7 (EC:1.1.1.181).
Synonyms
  1. 3 beta,7 alpha-Dihydroxy-5-cholesten-26-oic acid
  2. 3,7-dihydroxy-5-cholestenoic acid
  3. 3beta,7alpha-Dihydroxy-5-cholesten-26-oic acid
  4. (3beta,7alpha)-3,7-dihydroxy-Cholest-5-en-26-oic acid
  5. 3 beta,7 alpha-Dihydroxy-5-cholesten-26-oate
  6. 3,7-dihydroxy-5-cholestenoate
  7. 3beta,7alpha-Dihydroxy-5-cholesten-26-oate
  8. (3beta,7alpha)-3,7-dihydroxy-Cholest-5-en-26-oate
Chemical IUPAC Name (6R)-6-[(3S,7S,8S,9S,10R,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylheptanoic acid
Chemical Formula C27H44O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
—
Class
—
Sub Class
—
Family
  • Mammalian Metabolite
Species
  • secondary alcohol
  • carboxylic acid
  • alkene
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 432.636
Monoisotopic Molecular Weight 432.323975
Isomeric SMILES C[C@H](CCCC(C)C(O)=O)C1CCC2C3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)C3CC[C@]12C
Canonical SMILES CC(CCCC(C)C(O)=O)C1CCC2C3C(O)C=C4CC(O)CCC4(C)C3CCC12C
KEGG Compound ID C17335 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12454 Link Image
Metagene Link HMDB12454 Link Image
METLIN ID Not Available
PubChem Compound 3081084 Link Image
PubChem Substance 36411955 Link Image
ChEBI ID Not Available
CAS Registry Number 115538-84-6
InChI Identifier InChI=1/C27H44O4/c1-16(6-5-7-17(2)25(30)31)20-8-9-21-24-22(11-13-27(20,21)4)26(3)12-10-19(28)14-18(26)15-23(24)29/h15-17,19-24,28-29H,5-14H2,1-4H3,(H,30,31)/t16-,17?,19+,20?,21?,22?,23-,24?,26+,27-/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 6.90e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.92 [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 7B1
Enzyme 1 [top]
Enzyme 1 ID 6952
Enzyme 1 Name Cytochrome P450 7B1
Enzyme 1 Synonyms
  1. 25-hydroxycholesterol 7-alpha- hydroxylase
  2. Oxysterol 7-alpha-hydroxylase
Enzyme 1 Gene Name CYP7B1
Enzyme 1 Protein Sequence >Cytochrome P450 7B1 
MAGEVSAATGRFSLERLGLPGLALAAALLLLALCLLVRRTRRPGEPPLIKGWLPYLGVVL
NLRKDPLRFMKTLQKQHGDTFTVLLGGKYITFILDPFQYQLVIKNHKQLSFRVFSNKLLE
KAFSISQLQKNHDMNDELHLCYQFLQGKSLDILLESMMQNLKQVFEPQLLKTTSWDTAEL
YPFCSSIIFEITFTTIYGKVIVCDNNKFISELRDDFLKFDDKFAYLVSNIPIELLGNVKS
IREKIIKCFSSEKLAKMQGWSEVFQSRQDVLEKYYVHEDLEIGAHHLGFLWASVANTIPT
MFWAMYYLLRHPEAMAAVRDEIDRLLQSTGQKKGSGFPIHLTREQLDSLICLESSIFEAL
RLSSYSTTIRFVEEDLTLSSETGDYCVRKGDLVAIFPPVLHGDPEIFEAPEEFRYDRFIE
DGKKKTTFFKRGKKLKCYLMPFGTGTSKCPGRFFALMEIKQLLVILLTYFDLEIIDDKPI
GLNYSRLLFGIQYPDSDVLFRYKVKS
Enzyme 1 Number of Residues 506
Enzyme 1 Molecular Weight 58257
Enzyme 1 Theoretical pI 8.13
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 Cholest-5-ene-3-beta,25-diol + NADPH + O(2) = cholest-5-ene-3-beta,7-alpha,25-triol + NADP(+) + H(2)O
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • 1-40
Enzyme 1 Transmembrane Regions
  • 287-309
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 3702794 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID O75881 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name CP7B1_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1521 bp 
ATGGCAGGAGAAGTGTCCGCGGCCACGGGCCGCTTTTCGCTGGAGCGGTTGGGCCTCCCG
GGCCTGGCCCTCGCCGCGGCCCTGCTGCTCCTGGCCCTCTGCTTGCTTGTCCGGCGCACC
AGGAGACCCGGTGAGCCTCCATTGATAAAAGGTTGGCTTCCTTATCTTGGAGTGGTCCTG
AACTTACGAAAAGACCCCTTAAGGTTCATGAAAACACTTCAAAAGCAACATGGTGACACT
TTCACAGTTCTTCTTGGTGGAAAGTACATAACATTTATCCTGGACCCCTTCCAGTACCAG
CTAGTGATAAAAAATCATAAACAATTAAGCTTTCGAGTATTTTCTAATAAATTATTAGAG
AAAGCATTTAGCATCAGTCAGTTGCAAAAAAATCATGACATGAATGATGAGCTTCACCTC
TGCTATCAATTTTTGCAAGGCAAATCTTTGGACATACTCTTGGAAAGCATGATGCAGAAT
CTAAAACAAGTTTTTGAACCCCAGCTGTTAAAAACCACAAGTTGGGACACGGCAGAACTG
TATCCATTCTGCAGCTCAATAATATTTGAGATCACATTTACAACTATATATGGAAAAGTT
ATTGTTTGTGACAACAACAAATTTATTAGTGAGCTAAGAGATGATTTTTTAAAATTTGAT
GACAAGTTTGCATATTTAGTATCCAACATACCCATTGAGCTTCTAGGAAATGTCAAGTCT
ATTAGAGAGAAAATTATAAAATGCTTCTCATCAGAAAAGTTAGCCAAGATGCAAGGATGG
TCAGAAGTTTTTCAAAGCAGGCAAGATGTCCTGGAGAAATATTATGTGCACGAGGACCTT
GAAATAGGAGCACATCATTTAGGCTTTCTCTGGGCCTCTGTGGCAAACACTATTCCAACT
ATGTTCTGGGCAATGTATTATCTTCTGCGGCACCCAGAAGCTATGGCAGCAGTGCGTGAC
GAAATTGACCATTTGCTGCAGTCAACAGGTCAAAAGAAAGGGTCTGGATTTCCCATCCAC
CTCACCAGAGAACAATTGGACAGCCTAATCTGCCTAGAAAGCAGCATTTTTGAAGCTTTA
CGACTGTCCTCATATTCAACCACCATTCGTTTTGTTGAGGAGGATTTGACTCTCAGTTCA
GAGACCGGGGACTACTGTGTGCGAAAGGGAGACTTGGTAGCCATCTTTCCTCCAGTCCTA
CATGGTGACCCTGAAATCTTTGAAGCTCCAGAGGAGTTTAGATATGATCGTTTTATAGAA
GATGGTAAGAAGAAAACCACCTTTTTCAAAAGAGGGAAAAAGCTGAAGTGTTACCTAATG
CCGTTTGGAACTGGAACCAGCAAATGTCCAGGCCGATTTTTTGCACTTATGGAAATAAAA
CAATTGTTGGTTATACTTTTAACTTATTTTGATTTAGAAATAATTGATGATAAGCCCATA
GGACTAAACTACAGCCGCTTGTTGTTTGGTATTCAGTATCCAGATTCTGATGTTTTATTT
AGATACAAAGTGAAATCTTAG
Enzyme 1 GenBank Gene ID AF029403 Link Image
Enzyme 1 GeneCard ID CYP7B1 Link Image
Enzyme 1 GenAtlas ID CYP7B1 Link Image
Enzyme 1 HGNC ID HGNC:2652 Link Image
Enzyme 1 Chromosome Location 8
Enzyme 1 Locus 8q21.3
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Setchell KD, Schwarz M, O'Connell NC, Lund EG, Davis DL, Lathe R, Thompson HR, Weslie Tyson R, Sokol RJ, Russell DW: Identification of a new inborn error in bile acid synthesis: mutation of the oxysterol 7alpha-hydroxylase gene causes severe neonatal liver disease. J Clin Invest. 1998 Nov 1;102(9):1690-703. [PubMed Link Image]
  2. Wu Z, Martin KO, Javitt NB, Chiang JY: Structure and functions of human oxysterol 7alpha-hydroxylase cDNAs and gene CYP7B1. J Lipid Res. 1999 Dec;40(12):2195-203. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available