Record Information
Version1.0
Creation date2011-09-21 00:07:46 UTC
Update date2015-10-09 22:30:57 UTC
Primary IDFDB022059
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameNutriacholic 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 Number4651-67-6
Structure
Thumb
Synonyms
SynonymSource
NutriacholateGenerator
3a-Hydroxy-7-oxo-5b-cholanoateHMDB
3a-Hydroxy-7-oxo-5b-cholanoic acidHMDB
5b-Cholanic acid-3a-ol-7-oneHMDB
7-KetochenodeoxycholateHMDB
7-Ketochenodeoxycholic acidHMDB
7-KetolithocholateHMDB
7-Ketolithocholic acidHMDB
7-oxo-3a-Hydroxycholan-24-OateHMDB
7-oxo-3a-Hydroxycholan-24-Oic acidHMDB
7-OxolithocholateHMDB
7-Oxolithocholic acidHMDB
3 alpha-Hydroxy-7-keto-5 beta-cholanoateHMDB
3 alpha-Ol-7-one-5 beta-cholanoic acidHMDB
7-Ketolithocholic acid, (3beta,5alpha)-isomerHMDB
(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-Hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]pentanoateHMDB
3a-hydroxy-7-oxo-5b-cholanoatehmdb
3a-hydroxy-7-oxo-5b-cholanoic acidhmdb
7-Oxo-3a-hydroxycholan-24-oatehmdb
7-Oxo-3a-hydroxycholan-24-oic acidhmdb
Nutriacholic acidhmdb
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP3.52ALOGPS
logP4.1ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.56ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity108.35 m³·mol⁻¹ChemAxon
Polarizability44.94 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC24H38O4
IUPAC name(4S)-4-[(1S,2S,5R,7S,10R,11S,15R)-5-hydroxy-2,15-dimethyl-9-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]pentanoic acid
InChI IdentifierInChI=1S/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/h14-19,22,25H,4-13H2,1-3H3,(H,27,28)/t14-,15-,16+,17?,18-,19-,22-,23-,24+/m0/s1
InChI KeyDXOCDBGWDZAYRQ-QPVZPPSOSA-N
Isomeric SMILES[H][C@@]12CCC([C@@H](C)CCC(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])C(=O)C[C@]2([H])C[C@H](O)CC[C@]12C
Average Molecular Weight390.5561
Monoisotopic Molecular Weight390.277009704
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-hydroxysteroid
  • Hydroxysteroid
  • 7-oxosteroid
  • 3-alpha-hydroxysteroid
  • Oxosteroid
  • Cyclic alcohol
  • 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:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNutriacholic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03gj-0319000000-99c0cf456750a298fdbaSpectrum
Predicted GC-MSNutriacholic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01b9-2141590000-df782bc25f3fffc7b8b0Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0291000000-9f5bf5f94dd6944d6d6fSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-052r-2962000000-f18d1686d1ac8b6e93f3Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05o1-2900000000-681b2fd8ee33b91d7a44Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05fr-0009000000-96e2b732bac67ff31b5cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-076s-0009000000-63349742d082a77d840fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01t9-0229000000-c96c7b6b3568bc1568ecSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-bcd0337fb08276e5242bSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dr-0009000000-8e05a17c162e99bd54edSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9006000000-ddfed24aad7a991420faSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-1bf3e4a9164eecd8b5adSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0079-0009000000-dabdf5ac37340fa8a343Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052r-3029000000-ec70dabf7a7d2522ff70Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0596-0009000000-aa05b3718c19db13d245Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-2059000000-993d476f495649000a3fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0adj-2931000000-238650ed3f34647466ebSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477693
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00467
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
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference