Trihydroxycoprostanoic acid (CHEM035349)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:40:52 UTC
Update Date2016-11-09 01:21:17 UTC
Accession NumberCHEM035349
Identification
Common NameTrihydroxycoprostanoic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
TrihydroxycoprostanoateGenerator
(3a,5b,7a,12a)-3,7,12-Trihydroxy-cholestane-5-carboxylateHMDB
(3a,5b,7a,12a)-3,7,12-Trihydroxy-cholestane-5-carboxylic acidHMDB
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-5-carboxylateHMDB
(3alpha,5beta,7alpha,12alpha)-3,7,12-Trihydroxycholestane-5-carboxylic acidHMDB
3,7,12-TrihydroxycoprostanateHMDB
3,7,12-Trihydroxycoprostanic acidHMDB
3alpha,7alpha,12alpha-TrihydroxycoprostanateHMDB
3alpha,7alpha,12alpha-Trihydroxycoprostanic acidHMDB
5-ThcaHMDB
TryhydroxycoprostanateHMDB
Tryhydroxycoprostanic acidHMDB
3 alpha,7 alpha,12 alpha-Trihydroxy-5 beta-cholestanoic acidHMDB
3 alpha,7 alpha,12 alpha-Trihydroxycoprostanic acidHMDB
(1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-Trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylateHMDB
Chemical FormulaC28H48O5
Average Molecular Mass464.678 g/mol
Monoisotopic Mass464.350 g/mol
CAS Registry Number863-39-8
IUPAC Name(1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylic acid
Traditional Name(1S,2R,5R,7R,9R,10R,11S,14R,15R,16S)-5,9,16-trihydroxy-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane-7-carboxylic acid
SMILES[H][C@@]12CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)[C@@H](O)C[C@@]1([H])[C@@]2([H])[C@H](O)C[C@@]2(C[C@H](O)CC[C@]12C)C(O)=O
InChI IdentifierInChI=1S/C28H48O5/c1-16(2)7-6-8-17(3)19-9-10-20-24-21(13-23(31)27(19,20)5)26(4)12-11-18(29)14-28(26,25(32)33)15-22(24)30/h16-24,29-31H,6-15H2,1-5H3,(H,32,33)/t17-,18-,19-,20+,21+,22-,23+,24+,26-,27-,28+/m1/s1
InChI KeyJIFNDZCDNLFAKC-YAODFNMUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassCholestane steroids
Direct ParentCholesterols and derivatives
Alternative Parents
Substituents
  • Cholesterol
  • Cholesterol-skeleton
  • Steroid acid
  • 3-hydroxysteroid
  • 12-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • 7-hydroxysteroid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Polyol
  • Carboxylic acid derivative
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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 Solubility0.013 g/LALOGPS
logP3.51ALOGPS
logP4.47ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.35ChemAxon
pKa (Strongest Basic)-0.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity129.07 m³·mol⁻¹ChemAxon
Polarizability55.37 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006w-1151900000-9964b763512a2672587eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-3214059000-4094305c0a69ba80bb14Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0000900000-b0a4411cb2684a1a2972Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fba-1101900000-990e05e4698fd587ab83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avi-8404900000-1b74f95b874b3c97fd32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03dj-0000900000-bad6122da3518cc7d5b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0wmj-0000900000-e2d7732c54b6600adc8aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0v00-1002900000-8baa3514da0d45921e79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0000900000-915fa80269f79ccefd03Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0000900000-f34f75240f81eb3f52f1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-0003900000-546ed85bdaefe541670eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014j-0000900000-3f74f7ede1344fce4d83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-5103900000-7ac26fb2207619da057aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9322000000-2321f8e3f4c0e7f6b080Spectrum
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 IDHMDB0002163
FooDB IDFDB022877
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6519
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID108961
ChEBI ID89753
PubChem Compound ID122166
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Casteels M, Van Roermund CW, Schepers L, Govaert L, Eyssen HJ, Mannaerts GP, Wanders RJ: Deficient oxidation of trihydroxycoprostanic acid in liver homogenates from patients with peroxisomal diseases. J Inherit Metab Dis. 1989;12(4):415-22.
2. Wanders RJ, Schutgens RB, Heymans HS: Deficient cholesterol side chain oxidation in patients without peroxisomes (Zellweger syndrome): evidence for the involvement of peroxisomes in bile acid synthesis in man. Clin Chim Acta. 1987 Feb 15;162(3):295-301.
3. Muller-Hocker J, Bise K, Endres W, Hubner G: [Morphology and diagnosis of Zellweger syndrome. A contribution to combined cytochemical-finestructural identification of peroxisomes in autopsy material and frozen liver tissue with case report]. Virchows Arch A Pathol Anat Histol. 1981;393(1):103-14.