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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:59:09 UTC
Update Date2018-03-12 22:06:20 UTC
HMDB IDHMDB0034191
Secondary Accession Numbers
  • HMDB34191
Metabolite Identification
Common NameWithaperuvin B
DescriptionWithaperuvin b belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Thus, withaperuvin b is considered to be a sterol lipid molecule. Withaperuvin b exists as a solid, slightly soluble (in water), and a very weakly acidic compound (based on its pKa). Withaperuvin b has been found in human hepatic tissue tissue, and has also been primarily detected in urine. Within the cell, withaperuvin b is primarily located in the cytoplasm. Outside of the human body, withaperuvin b can be found in fruits. This makes withaperuvin b a potential biomarker for the consumption of this food product.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC28H40O9
Average Molecular Weight520.6118
Monoisotopic Molecular Weight520.267232878
IUPAC Name6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydro-2H-pyran-2-one
Traditional Name6-(1-hydroxy-1-{6,7,8,11,14-pentahydroxy-2,15-dimethyl-3-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-4-en-14-yl}ethyl)-3,4-dimethyl-5,6-dihydropyran-2-one
CAS Registry Number81644-35-1
SMILES
CC1=C(C)C(=O)OC(C1)C(C)(O)C1(O)CCC2(O)C3CC(O)C4(O)C(O)C=CC(=O)C4(C)C3CCC12C
InChI Identifier
InChI=1S/C28H40O9/c1-14-12-21(37-22(32)15(14)2)25(5,33)27(35)11-10-26(34)17-13-20(31)28(36)19(30)7-6-18(29)24(28,4)16(17)8-9-23(26,27)3/h6-7,16-17,19-21,30-31,33-36H,8-13H2,1-5H3
InChI KeyXLUKITCTLVOOAW-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid lactones
Direct ParentWithanolides and derivatives
Alternative Parents
Substituents
  • Withanolide-skeleton
  • 20-hydroxysteroid
  • 4-hydroxysteroid
  • 14-hydroxysteroid
  • 6-hydroxysteroid
  • 5-hydroxysteroid
  • Hydroxysteroid
  • 1-oxosteroid
  • Oxosteroid
  • 17-hydroxysteroid
  • Cyclohexenone
  • Dihydropyranone
  • Pyran
  • Tertiary alcohol
  • Cyclic alcohol
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Secondary alcohol
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Route of exposure:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point269 - 270 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.04 g/LALOGPS
logP0.64ALOGPS
logP0.61ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)12.17ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area164.75 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity133.13 m³·mol⁻¹ChemAxon
Polarizability55.2 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udr-0489740000-3e53806f47d33a03eeb0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001a-3341269000-eb405f656e4d60540d77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0003490000-0a25379c004e3e6d9aa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ue9-7114930000-fcadccfe4fc5a33f4ef5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-3039000000-98bff6858130e8d7d45eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-016r-0103590000-b13bde068d144f6591bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gc0-1906220000-abdbc48f76a634c478b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9304000000-1608f0e187d3d78a514cView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012487
KNApSAcK IDNot Available
Chemspider ID2965197
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3734964
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.