3b-Hydroxy-5-cholenoic acid (CHEM022408)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:31:43 UTC
Update Date2016-11-09 01:17:30 UTC
Accession NumberCHEM022408
Identification
Common Name3b-Hydroxy-5-cholenoic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3b-Hydroxy-5-cholenoateGenerator
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, MeSH
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, HMDB
3 beta-Hydroxy-delta 5-cholenic acid, sodium saltMeSH, HMDB
3 beta-Hydroxy-delta 5-cholenic acidMeSH, HMDB
3 beta-Hydroxy-5-cholenoic acidMeSH, HMDB
(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]pentanoateGenerator, HMDB
Chemical FormulaC24H38O3
Average Molecular Mass374.557 g/mol
Monoisotopic Mass374.282 g/mol
CAS Registry Number5255-17-4
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 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
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 IdentifierInChI=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
Description 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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Polarizability45.29 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ktb-0119000000-d9c374e9f5f5293a5dcaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udi-2115890000-77f8ec28775146b3a80aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4j-9538000000-967e828abd3f3d7ea705Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00kf-9800000000-fd3b7c3599b83e132518Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0w29-1695000000-3a7e6bdffc7807847034Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-d81080951979776b8851Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvr-0029000000-57d452e5f3215053dec5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-2296000000-bc9371e40f0a8181ee48Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-5f1cbb9d5b0d94fca8aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-0009000000-81084972d3f11745deaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-cc93a4f9f513c8d5c003Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-666fef074d788c106dcbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05fr-0009000000-7995f4531885f9d2edf6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-4059000000-4a851016b0c31ca828caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0009000000-589eec7541e9d9499e9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-3298000000-26204184430e4b9552c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3941000000-109ac8dcc89c0c4c8858Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0000308
FooDB IDFDB021935
Phenol Explorer IDNot Available
KNApSAcK IDC00052229
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID5297
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID83950
ChEBI ID384794
PubChem Compound ID92997
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDECMDB24031
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
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.
4. 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.
5. Norman A, Strandvik B: Formation and metabolism of bile acids in extrahepatic biliary atresia. J Lab Clin Med. 1971 Aug;78(2):181-93.
6. 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.