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Bovine Metabolome Database



Showing metabocard for 7a-Hydroxy-3-oxo-5b-cholanoic acid (BMDB00503)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-06-20 11:02:41
Accession Number BMDB00503
Common Name 7a-Hydroxy-3-oxo-5b-cholanoic acid
Description Glycine- and taurine-conjugated 7 alpha-hydroxy-3-oxo-5 beta-cholanoic acid has been identified in normal human serum (PMID 1939467) and as a cholesterol metabolite in bile acids produced in HepG2 cells -a well-differentiated human hepatoblastoma cell line. (PMID 1655725)
Synonyms
  1. (5b,7a)-7-hydroxy-3-oxo-Cholan-24-oate
  2. (5b,7a)-7-hydroxy-3-oxo-Cholan-24-oic acid
  3. 7a-Hydroxy-3-oxo-5b-cholanoate
  4. 7a-hydroxy-3-oxo-5b-cholanoic acid
Chemical IUPAC Name Not Available
Chemical Formula C24H38O4
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Bile Acids
Sub Class
  • Monohydroxy bile acids
Family
  • Mammalian_Metabolite
Species
  • ketone; secondary alcohol; carboxylic acid
Biofunction
  • Fat solubilization and Waste products
Application
Source
  • Endogenous
Average Molecular Weight 390.556
Monoisotopic Molecular Weight 390.277008
Isomeric SMILES C[C@H](CCC(O)=O)C1CC[C@H]2[C@@H]3[C@H](O)C[C@@H]4CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC(CCC(O)=O)C1CCC2C3C(O)CC4CC(=O)CCC4(C)C3CCC12C
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID 5489 Link Image
PubChem Compound Not Available
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number 4185-00-6
InChI Identifier InChI=1/C24H38O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-15,17-20,22,26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,17?,18+,19+,20?,22+,23+,24-/m1/s1
Synthesis Reference Riva, Sergio; Bovara, Roberto; Zetta, Lucia; Pasta, Piero; Ottolina, Gianluca; Carrea, Giacomo. Enzymic a/b inversion of C-3 hydroxyl of bile acids and study of the effects of organic solvents on reaction rates. Journal of Organic Chemistry (1988), 53(1), 88-92.
Melting Point (Experimental) 88-90 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 0.0152 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.11 [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 Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location
Tissue References
Liver
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available