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Showing Compound 12alpha-Hydroxy-3-oxocholadienic acid (FDB022003)

Record Information
Version1.0
Creation date2011-09-21 00:06:49 UTC
Update date2015-07-21 06:56:56 UTC
Primary IDFDB022003
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name12alpha-Hydroxy-3-oxocholadienic acid
DescriptionA bile acid. Bile acids are steroid acids found predominantly in bile of mammals. The distinction between different bile acids is minute, depends only on presence or absence of hydroxyl groups on positions 3, 7, and 12. Bile acids are physiological detergents that facilitate excretion, absorption, and transport of fats and sterols in the intestine and liver. Bile acids are also steroidal amphipathic molecules derived from the catabolism of cholesterol. They modulate bile flow and lipid secretion, are essential for the absorption of dietary fats and vitamins, and have been implicated in the regulation of all the key enzymes involved in cholesterol homeostasis. Bile acids recirculate through the liver, bile ducts, small intestine and portal vein to form an enterohepatic circuit. They exist as anions at physiological pH and, consequently, require a carrier for transport across the membranes of the enterohepatic tissues. The unique detergent properties of bile acids are essential for the digestion and intestinal absorption of hydrophobic nutrients. Bile acids have potent toxic properties (e.g., membrane disruption) and there are a plethora of mechanisms to limit their accumulation in blood and tissues. (PMID: 11316487, 16037564, 12576301, 11907135) [HMDB]
CAS Number13535-96-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.022 g/LALOGPS
logP3.49ALOGPS
logP3.59ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-0.35ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity110.11 m³·mol⁻¹ChemAxon
Polarizability43.64 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H34O4
IUPAC name(4R)-4-[(2R,15R,16S)-16-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-6,8-dien-14-yl]pentanoic acid
InChI IdentifierInChI=1S/C24H34O4/c1-14(4-9-22(27)28)18-7-8-19-17-6-5-15-12-16(25)10-11-23(15,2)20(17)13-21(26)24(18,19)3/h5-6,12,14,17-21,26H,4,7-11,13H2,1-3H3,(H,27,28)/t14-,17?,18?,19?,20?,21+,23+,24-/m1/s1
InChI KeyDJVAMCYXFUWMLS-RVOJYKBWSA-N
Isomeric SMILESC[C@H](CCC(O)=O)C1CCC2C3C=CC4=CC(=O)CC[C@]4(C)C3C[C@H](O)[C@]12C
Average Molecular Weight386.5244
Monoisotopic Molecular Weight386.245709576
Classification
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-oxosteroid
  • 12-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • Cyclohexenone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-08mi-1749000000-de114046c628c58a5eddSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-014i-2191170000-9998846ffacee5e0677fSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS12alpha-Hydroxy-3-oxocholadienic acid, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0009000000-290d4eb4d249b16fe3e02017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lkc-0009000000-d7e470c0215474a295202017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-5219000000-a8d56d9c39447200b4ca2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-b0caf18090f9ef4bb2932017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014r-0009000000-669414e6c6b47067fe222017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-dd833c9fd22521dce7742017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-c8a026dd6116a869f5962021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-4e9f4a976c84950f587b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00li-0098000000-686efde5f229f343a4f42021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-0019000000-30bbb01212141ac76f2f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fri-2179000000-03bf59bf72ad64ad8f032021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adl-4931000000-9780a1a303ef6253957c2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477691
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00385
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference