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Human Metabolome Database Version 3.5

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Showing metabocard for 3b-Hydroxy-5-cholenoic acid (HMDB00308)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:17 -0700
HMDB ID HMDB00308
Secondary Accession Numbers None
Metabolite Identification
Common Name 3b-Hydroxy-5-cholenoic acid
Description 3b-Hydroxy-5-cholenoic acid is a monohydroxy bile acid of endogenous origin. It is found in biologic fluids beginning in fetal life. (PMID 5567561 Link_out; 4803245; 93138) Large amounts of 3 beta-hydroxy-5-cholenoic acid could be found in children with the syndrome of hepatic ductular hypoplasia (PMID 3987031 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 3b-Hydroxy-5-cholenoate
  2. 3b-Hydroxy-5-cholenoic acid
  3. 3b-Hydroxy-chol-5-en-24-oate
  4. 3b-Hydroxy-chol-5-en-24-oic acid
  5. 3b-Hydroxychol-5-en-24-ate
  6. 3b-Hydroxychol-5-en-24-ic acid
  7. 3b-Hydroxychol-5-en-24-oate
  8. 3b-Hydroxychol-5-en-24-oic acid
  9. 3b-Hydroxychol-5-enoate
  10. 3b-Hydroxychol-5-enoic acid
  11. 3b-Hydroxycholenoate
  12. 3b-Hydroxycholenoic acid
  13. 3beta-Hydroxy-5-cholenic acid
  14. 3beta-Hydroxy-5-cholenoate
  15. 3beta-Hydroxy-5-cholenoic acid
  16. 3beta-Hydroxy-chol-5-en-24-oate
  17. 3beta-Hydroxy-chol-5-en-24-oic acid
  18. 3beta-Hydroxy-delta5-cholenic acid
  19. 3beta-Hydroxychol-5-en-24-oate
  20. 3beta-Hydroxychol-5-en-24-oic acid
  21. Cholenate
  22. Cholenic acid
  23. D5-Cholenate
  24. D5-Cholenic acid
Chemical Formula C24H38O3
Average Molecular Weight 374.5567
Monoisotopic Molecular Weight 374.282095082
IUPAC Name (4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid
Traditional IUPAC Name (4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]pentanoic acid
CAS Registry Number 5255-17-4
SMILES [H][C@@]12CC[C@H]([C@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C
InChI Identifier InChI=1S/C24H38O3/c1-15(4-9-22(26)27)19-7-8-20-18-6-5-16-14-17(25)10-12-23(16,2)21(18)11-13-24(19,20)3/h5,15,17-21,25H,4,6-14H2,1-3H3,(H,26,27)/t15-,17+,18+,19-,20+,21+,23+,24-/m1/s1
InChI Key HIAJCGFYHIANNA-QIZZZRFXSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Steroids and Steroid Derivatives
Sub Class Bile Acids, Alcohols and Derivatives
Other Descriptors
  • Aliphatic Homopolycyclic Compounds
  • Bile Acids, Alcohols and Derivatives
  • C24 bile acids, alcohols, and derivatives(Lipidmaps)
  • Monohydroxy Bile Acids, Alcohols and Derivatives
Substituents
  • 3 Hydroxy Steroid
  • Bicyclohexane
  • Carboxylic Acid
  • Cyclic Alcohol
  • Cyclohexane
  • Cyclohexene
  • Secondary Alcohol
Direct Parent Hydroxy Bile Acids, Alcohols and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fat solubilization and Waste products
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
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 0.0035 g/L ALOGPS
LogP 4.54 ALOGPS
LogP 4.62 ChemAxon
LogS -5.02 ALOGPS
pKa (strongest acidic) 4.83 ChemAxon
pKa (strongest basic) -1.4 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 57.53 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 108.53 ChemAxon
Polarizability 45.31 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Expected and not Quantified
Not Applicable Not Available Not Available Normal Inferred from detection in urine
Urine Detected and Quantified
Article_icon
0.015 (0.004-0.030) umol/mmol creatinine Adult (>18 years old) Both Normal by GC-MS
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 FDB021935
KNApSAcK ID Not Available
Chemspider ID 83950 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00308 Link_out
Metagene Link HMDB00308 Link_out
METLIN ID 5297 Link_out
PubChem Compound 92997 Link_out
PDB ID Not Available
ChEBI ID 384794 Link_out
References
Synthesis Reference Burton, Gerardo; Gros, Eduardo G. Synthesis of 3b-hydroxy-5-cholenic acid from 3b-hydroxy-5-pregnen-20-one aimed at the preparation of labeled steroid compounds. Journal of Steroid Biochemistry (1977), 8(1), 69-72.
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005 Link_out
  2. Vanderpas JB, Koopman BJ, Cadranel S, Vandenbergen C, Rickaert F, Quenon M, Wolthers BG, Brauherz G, Vertongen F, Tondeur M: Malabsorption of liposoluble vitamins in a child with bile acid deficiency. J Pediatr Gastroenterol Nutr. 1987 Jan-Feb;6(1):33-41. Pubmed: 3794931 Link_out
  3. Kimura A, Mahara R, Inoue T, Nomura Y, Murai T, Kurosawa T, Tohma M, Noguchi K, Hoshiyama A, Fujisawa T, Kato H: Profile of urinary bile acids in infants and children: developmental pattern of excretion of unsaturated ketonic bile acids and 7beta-hydroxylated bile acids. Pediatr Res. 1999 Apr;45(4 Pt 1):603-9. Pubmed: 10203155 Link_out
Enzymes
Name: Gastrotropin
Reactions:
    Gene Name: FABP6
    Uniprot ID: P51161 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Transporters
    Name: Solute carrier organic anion transporter family member 1B3
    Reactions:
    • --- []
    Gene Name: SLCO1B3
    Uniprot ID: Q9NPD5 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Solute carrier organic anion transporter family member 1B1
    Reactions:
    • --- []
    Gene Name: SLCO1B1
    Uniprot ID: Q9Y6L6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Canalicular multispecific organic anion transporter 2
    Reactions:
    • --- []
    Gene Name: ABCC3
    Uniprot ID: O15438 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Bile salt export pump
    Reactions:
    • --- []
    Gene Name: ABCB11
    Uniprot ID: O95342 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ileal sodium/bile acid cotransporter
    Reactions:
    • --- []
    Gene Name: SLC10A2
    Uniprot ID: Q12908 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Sodium/bile acid cotransporter
    Reactions:
    • --- []
    Gene Name: SLC10A1
    Uniprot ID: Q14973 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Solute carrier organic anion transporter family member 1A2
    Reactions:
    • --- []
    Gene Name: SLCO1A2
    Uniprot ID: P46721 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Solute carrier organic anion transporter family member 4A1
    Reactions:
    • --- []
    Gene Name: SLCO4A1
    Uniprot ID: Q96BD0 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA