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Showing Compound Withanolide (FDB023125)

Record Information
Version1.0
Creation date2011-09-21 00:25:03 UTC
Update date2015-07-21 06:57:31 UTC
Primary IDFDB023125
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameWithanolide
DescriptionWithanolides, which are extracted from Withania somnifera, are employed in the treatment of arthritis and are known to be potent inhibitors of angiogenesis, inflammation and oxidative stress. Withanolides can indeed inhibit the activation of NF-κB and NF-κB-regulated gene expression, which could explain their anti-arthritic actions. W. somnifera root powder has suppressive effect on arthritis by reducing amplification and propagation of the inflammatory response, without causing any gastric damage. (PMID: 17475558, 3248848, 17084827) [HMDB]
CAS Number30655-48-2
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP2.7ALOGPS
logP3.78ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)13.28ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area96.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity126.87 m³·mol⁻¹ChemAxon
Polarizability52.31 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC28H38O6
IUPAC name(1S,2R,6S,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-4-en-3-one
InChI IdentifierInChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28?/m0/s1
InChI KeySASUFNRGCZMRFD-LYOLWDNZSA-N
Isomeric SMILES[H][C@@]12C[C@@]3([H])[C@]4([H])CC[C@]([H])([C@@](C)(O)[C@@]5([H])CC(C)=C(C)C(=O)O5)[C@@]4(C)CC[C@]3([H])[C@@]3(C)C(=O)C=C[C@H](O)C13O2
Average Molecular Weight470.5977
Monoisotopic Molecular Weight470.266838948
Classification
Description 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
  • 5,6-epoxysteroid
  • Dihydropyranone
  • Oxepane
  • Cyclohexenone
  • Pyran
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tertiary alcohol
  • Carboxylic acid ester
  • Ketone
  • Lactone
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Dialkyl ether
  • Oxirane
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSWithanolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-1001-2139300000-7e60985d09b64f878a12Spectrum
Predicted GC-MSWithanolide, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fdt-6019352000-44dbe9f9faffca66370eSpectrum
Predicted GC-MSWithanolide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0002900000-1f52202c63cf953f90782017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-9026800000-7b1e1aaed10af48e838a2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-5194100000-075f5c9753e4896a1d302017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0001900000-876c22194e6f1a97bbd82017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-2728900000-64910a535ac954980abd2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9202000000-1a1334a54e34414dde7b2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000900000-825df051d2576a60db7f2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-1003900000-d0175cc6da223a727be92021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-015c-9303400000-c136a80072fdee60bade2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0003900000-0cf474e82baf6ca1efc02021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-5259600000-e46a909d3428f66c13932021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-11ca-5196300000-3af868c3b54465fd160a2021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC08842
Pubchem Compound ID53477765
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB03218
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
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference