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Varanic acid (FDB022897)

Record Information
Version1.0
Creation date2011-09-21 00:21:18 UTC
Update date2015-07-21 06:57:25 UTC
Primary IDFDB022897
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameVaranic acid
DescriptionVaranic acid is a bile acid that will accumulate in patients with deficiencies in the peroxisomal d-bifunctional protein. The final steps in bile acid biosynthesis take place in peroxisomes and involve oxidative cleavage of the side chain of C27-5beta-cholestanoic acids leading to the formation of the primary bile acids cholic acid and chenodeoxycholic acid. The enoyl-CoA hydratase and beta-hydroxy acyl-CoA dehydrogenase reactions involved in the chain shortening of C27-5beta-cholestanoic acids are catalyzed by peroxisomal d-bifunctional protein. (PMID: 9831634) [HMDB]
CAS Number1061-64-9
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0081 g/LALOGPS
logP3.41ALOGPS
logP3.97ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity119.74 m³·mol⁻¹ChemAxon
Polarizability51.21 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H44O5
IUPAC name(2R,3R,6R)-2,3-dihydroxy-6-[(1S,2S,5R,7R,10R,11S,14R,15R)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-14-yl]heptanoic acid
InChI IdentifierInChI=1S/C26H44O5/c1-15(4-9-22(28)23(29)24(30)31)19-7-8-20-18-6-5-16-14-17(27)10-12-25(16,2)21(18)11-13-26(19,20)3/h15-23,27-29H,4-14H2,1-3H3,(H,30,31)/t15-,16-,17-,18+,19-,20+,21+,22-,23-,25+,26-/m1/s1
InChI KeyNRDKNLGDNLHWHG-IYELHLJQSA-N
Isomeric SMILES[H][C@@]12CC[C@H]([C@H](C)CC[C@@H](O)[C@@H](O)C(O)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])C[C@H](O)CC[C@]12C
Average Molecular Weight436.6246
Monoisotopic Molecular Weight436.318874518
Classification
Description Belongs to the class of organic compounds known as trihydroxy bile acids, alcohols and derivatives. These are prenol lipids structurally characterized by a bile acid or alcohol which bears three hydroxyl groups.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassBile acids, alcohols and derivatives
Direct ParentTrihydroxy bile acids, alcohols and derivatives
Alternative Parents
Substituents
  • Cholesterol-skeleton
  • Cholestane-skeleton
  • 25-hydroxysteroid
  • Trihydroxy bile acid, alcohol, or derivatives
  • 24-hydroxysteroid
  • Steroid acid
  • 3-hydroxysteroid
  • Hydroxysteroid
  • 3-alpha-hydroxysteroid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Alpha-hydroxy acid
  • Fatty acid
  • Fatty acyl
  • Hydroxy acid
  • Cyclic alcohol
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • 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
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-MSVaranic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0990-2009600000-03a9afbac544619ba649Spectrum
Predicted GC-MSVaranic acid, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-2201059000-728fa6a7dfdef5a44d71Spectrum
Predicted GC-MSVaranic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSVaranic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0003900000-bccb9b8d53d48b7a4eb92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0019400000-20845b139c4f42ddf3e92017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kg-1029100000-e64d24bdada468bf9ac62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1007900000-0c76a93c32d92d4bd0412017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00du-1009100000-89308fceaf5d08dd4f982017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9007000000-3244541b477b1a59c4c52017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-1002900000-b5d4ef16711be048d9d82021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adr-9005200000-432ff87864ffc7286a4c2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9006300000-553bfe38abe7822aeb9a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gic-0004900000-815713e2cdc936bf19cb2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ir0-1259400000-04ce9abd5182f75ecb612021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btd-9744000000-33ccfd422b6445ffcd7f2021-09-23View Spectrum
NMRNot Available
ChemSpider ID17216172
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID22833587
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02195
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference