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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:38:38 UTC
HMDB IDHMDB0000308
Secondary Accession Numbers
  • HMDB00308
Metabolite Identification
Common Name3b-Hydroxy-5-cholenoic acid
Description3b-Hydroxy-5-cholenoic acid is a monohydroxy bile acid of endogenous origin. It is found in biologic fluids beginning in fetal life. (PMID 5567561 ; 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 ).
Structure
Thumb
Synonyms
ValueSource
3b-Hydroxy-5-cholenoateHMDB
3b-Hydroxy-chol-5-en-24-OateHMDB
3b-Hydroxy-chol-5-en-24-Oic acidHMDB
3b-Hydroxychol-5-en-24-ateHMDB
3b-Hydroxychol-5-en-24-ic acidHMDB
3b-Hydroxychol-5-en-24-OateHMDB
3b-Hydroxychol-5-en-24-Oic acidHMDB
3b-Hydroxychol-5-enoateHMDB
3b-Hydroxychol-5-enoic acidHMDB
3b-HydroxycholenoateHMDB
3b-Hydroxycholenoic acidHMDB
3beta-Hydroxy-5-cholenic acidHMDB
3beta-Hydroxy-5-cholenoateHMDB
3beta-Hydroxy-5-cholenoic acidHMDB
3beta-Hydroxy-chol-5-en-24-OateHMDB
3beta-Hydroxy-chol-5-en-24-Oic acidHMDB
3beta-Hydroxy-delta5-cholenic acidHMDB
3beta-Hydroxychol-5-en-24-OateHMDB
3beta-Hydroxychol-5-en-24-Oic acidHMDB
CholenateHMDB
Cholenic acidHMDB
D5-CholenateHMDB
D5-Cholenic acidHMDB
3 beta-Hydroxy-5-cholenic acidMeSH
3 beta-Hydroxy-delta 5-cholenic acid, sodium saltMeSH
3 beta-Hydroxy-delta 5-cholenic acidMeSH
3 beta-Hydroxy-5-cholenoic acidMeSH
Chemical FormulaC24H38O3
Average Molecular Weight374.5567
Monoisotopic Molecular Weight374.282095082
IUPAC Name(4R)-4-[(1S,2R,5S,10S,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-yl]pentanoic acid
Traditional Namecholenic acid
CAS Registry Number5255-17-4
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 KeyHIAJCGFYHIANNA-QIZZZRFXSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as monohydroxy bile acids, alcohols and derivatives. These are bile acids, alcohols or any of their derivatives bearing a hydroxyl group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentMonohydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Monohydroxy bile acid, alcohol, or derivatives
  • 3-hydroxy-delta-5-steroid
  • 3-hydroxysteroid
  • 3-beta-hydroxysteroid
  • 3-beta-hydroxy-delta-5-steroid
  • Hydroxysteroid
  • Delta-5-steroid
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0035 g/LALOGPS
logP4.54ALOGPS
logP4.62ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.83ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.53 m³·mol⁻¹ChemAxon
Polarizability45.31 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ktb-0119000000-d9c374e9f5f5293a5dcaView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-2115890000-77f8ec28775146b3a80aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4j-9538000000-967e828abd3f3d7ea705View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9800000000-fd3b7c3599b83e132518View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w29-1695000000-3a7e6bdffc7807847034View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-d81080951979776b8851View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvr-0029000000-57d452e5f3215053dec5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-2296000000-bc9371e40f0a8181ee48View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-5f1cbb9d5b0d94fca8aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-0009000000-81084972d3f11745deaaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-cc93a4f9f513c8d5c003View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
Biofluid Locations
  • Blood
  • Saliva
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Both
    Normal
      • Zerihun T. Dame, ...
    details
    SalivaDetected but not Quantified Adult (>18 years old)Both
    Normal
      • Zerihun T. Dame, ...
    details
    UrineDetected and Quantified0.015 (0.004-0.030) umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB021935
    KNApSAcK IDNot Available
    Chemspider ID83950
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID5297
    PubChem Compound92997
    PDB IDNot Available
    ChEBI ID384794
    References
    Synthesis ReferenceBurton, 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 ]
    2. 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 ]
    3. 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 ]
    4. Norman A, Strandvik B: Formation and metabolism of bile acids in extrahepatic biliary atresia. J Lab Clin Med. 1971 Aug;78(2):181-93. [PubMed:5567561 ]
    5. Hernanz A, Codoceo R, Jara P, Diaz C: Unusual serum bile acid pattern in children with the syndrome of hepatic ductular hypoplasia. Clin Chim Acta. 1985 Feb 15;145(3):289-96. [PubMed:3987031 ]

    Enzymes

    General function:
    Involved in binding
    Specific function:
    Ileal protein which stimulates gastric acid and pepsinogen secretion. Seems to be able to bind to bile salts and bilirubins. Isoform 2 is essential for the survival of colon cancer cells to bile acid-induced apoptosis
    Gene Name:
    FABP6
    Uniprot ID:
    P51161
    Molecular weight:
    14371.2
    References
    1. Kurz M, Brachvogel V, Matter H, Stengelin S, Thuring H, Kramer W: Insights into the bile acid transportation system: the human ileal lipid-binding protein-cholyltaurine complex and its comparison with homologous structures. Proteins. 2003 Feb 1;50(2):312-28. [PubMed:12486725 ]

    Transporters

    General function:
    Involved in transporter activity
    Specific function:
    Mediates the Na(+)-independent transport of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotrexate and sulfobromophthalein (BSP)
    Gene Name:
    SLCO1B3
    Uniprot ID:
    Q9NPD5
    Molecular weight:
    77402.2
    General function:
    Involved in transporter activity
    Specific function:
    Mediates the Na(+)-independent transport of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostaglandin E2, thromboxane B2, leukotriene C3, leukotriene E4, thyroxine and triiodothyronine. May play an important role in the clearance of bile acids and organic anions from the liver
    Gene Name:
    SLCO1B1
    Uniprot ID:
    Q9Y6L6
    Molecular weight:
    76448.0
    References
    1. Michalski C, Cui Y, Nies AT, Nuessler AK, Neuhaus P, Zanger UM, Klein K, Eichelbaum M, Keppler D, Konig J: A naturally occurring mutation in the SLC21A6 gene causing impaired membrane localization of the hepatocyte uptake transporter. J Biol Chem. 2002 Nov 8;277(45):43058-63. Epub 2002 Aug 23. [PubMed:12196548 ]
    General function:
    Involved in ATP binding
    Specific function:
    May act as an inducible transporter in the biliary and intestinal excretion of organic anions. Acts as an alternative route for the export of bile acids and glucuronides from cholestatic hepatocytes
    Gene Name:
    ABCC3
    Uniprot ID:
    O15438
    Molecular weight:
    169341.1
    General function:
    Involved in ATP binding
    Specific function:
    Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes
    Gene Name:
    ABCB11
    Uniprot ID:
    O95342
    Molecular weight:
    146405.8
    General function:
    Involved in bile acid:sodium symporter activity
    Specific function:
    Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism
    Gene Name:
    SLC10A2
    Uniprot ID:
    Q12908
    Molecular weight:
    37697.4
    References
    1. Kramer W, Girbig F, Glombik H, Corsiero D, Stengelin S, Weyland C: Identification of a ligand-binding site in the Na+/bile acid cotransporting protein from rabbit ileum. J Biol Chem. 2001 Sep 21;276(38):36020-7. Epub 2001 Jul 10. [PubMed:11447228 ]
    General function:
    Involved in bile acid:sodium symporter activity
    Specific function:
    The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presence of sodium.
    Gene Name:
    SLC10A1
    Uniprot ID:
    Q14973
    Molecular weight:
    38118.64
    General function:
    Involved in transporter activity
    Specific function:
    Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids
    Gene Name:
    SLCO1A2
    Uniprot ID:
    P46721
    Molecular weight:
    74144.1
    General function:
    Involved in transporter activity
    Specific function:
    Mediates the Na(+)-independent transport of organic anions such as the thyroid hormones T3 (triiodo-L-thyronine), T4 (thyroxine) and rT3, and of estrone-3-sulfate and taurocholate
    Gene Name:
    SLCO4A1
    Uniprot ID:
    Q96BD0
    Molecular weight:
    77192.5