Varanic acid (CHEM035363)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:41:34 UTC
Update Date2016-11-09 01:21:18 UTC
Accession NumberCHEM035363
Identification
Common NameVaranic acid
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
VaranateGenerator
3a,7a,12a,24-Tetrahydroxy-5b-cholestan-26-OateHMDB
3a,7a,12a,24-Tetrahydroxy-5b-cholestan-26-Oic acidHMDB
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoateHMDB
3a,7a,12a,24-Tetrahydroxy-5b-cholestanoic acidHMDB
3alpha,7alpha,12alpha, 24-Tetrahydroxy-5beta-cholest-26-OateHMDB
3alpha,7alpha,12alpha, 24-Tetrahydroxy-5beta-cholest-26-Oic acidHMDB
BaranateHMDB
Baranic acidHMDB
(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]heptanoateGenerator, HMDB
Chemical FormulaC26H44O5
Average Molecular Mass436.625 g/mol
Monoisotopic Mass436.319 g/mol
CAS Registry Number1061-64-9
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
Traditional Namevaranic acid
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
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
Chemical Taxonomy
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
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 Solubility0.0081 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
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, Positivesplash10-0990-2009600000-03a9afbac544619ba649Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-000i-2201059000-728fa6a7dfdef5a44d71Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gb9-0003900000-bccb9b8d53d48b7a4eb9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0gb9-0019400000-20845b139c4f42ddf3e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kg-1029100000-e64d24bdada468bf9ac6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-1007900000-0c76a93c32d92d4bd041Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00du-1009100000-89308fceaf5d08dd4f98Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9007000000-3244541b477b1a59c4c5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kr-1002900000-b5d4ef16711be048d9d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adr-9005200000-432ff87864ffc7286a4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9006300000-553bfe38abe7822aeb9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0gic-0004900000-815713e2cdc936bf19cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ir0-1259400000-04ce9abd5182f75ecb61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btd-9744000000-33ccfd422b6445ffcd7fSpectrum
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 IDHMDB0002195
FooDB IDFDB022897
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID6538
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID17216172
ChEBI IDNot Available
PubChem Compound ID22833587
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Synthesis of diastereomers of 3 alpha,7 alpha,12 alpha, 24-tetrahydroxy- and 3 alpha,7 alpha,24-trihydroxy-5 beta-cholestan- 26-oic acids and their structures. Kurosawa T, Sato M, Nakano H, Tohma M. Steroids. 1996 Jul;61(7):421-8.
2. Vreken P, van Rooij A, Denis S, van Grunsven EG, Cuebas DA, Wanders RJ: Sensitive analysis of serum 3alpha, 7alpha, 12alpha,24-tetrahydroxy- 5beta-cholestan-26-oic acid diastereomers using gas chromatography-mass spectrometry and its application in peroxisomal D-bifunctional protein deficiency. J Lipid Res. 1998 Dec;39(12):2452-8.
3. Casteels M, Schepers L, Parmentier G, Eyssen HJ, Mannaerts GP: Activation and peroxisomal beta-oxidation of fatty acids and bile acid intermediates in liver from Bombina orientalis and from the rat. Comp Biochem Physiol B. 1989;92(1):129-32.
4. Clayton PT, Patel E, Lawson AM, Carruthers RA, Collins J: Bile acid profiles in peroxisomal 3-oxoacyl-coenzyme A thiolase deficiency. J Clin Invest. 1990 Apr;85(4):1267-73.