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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:42 UTC
Update Date2021-09-14 15:18:14 UTC
HMDB IDHMDB0003218
Secondary Accession Numbers
  • HMDB03218
Metabolite Identification
Common 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 ).
Structure
Data?1582752266
Synonyms
ValueSource
(4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-OateHMDB
(4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-Oic acidHMDB
(4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-Oic acid delta-lactoneHMDB
5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-OateHMDB
5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-Oic acidHMDB
5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-Oic acid delta-lactoneHMDB, MeSH
Withanolide DMeSH, HMDB
Dihydrowithanolide DMeSH, HMDB
Chemical FormulaC28H38O6
Average Molecular Weight470.5977
Monoisotopic Molecular Weight470.266838948
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
Traditional Name(1S,2R,6S,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-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
CAS Registry Number30655-48-2
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
InChI Identifier
InChI=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
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Fatty acid ester
  • Dialkyl phosphate
  • Dicarboxylic acid or derivatives
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic salt
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP10(2.7) g/LALOGPS
logP10(3.78) g/LChemAxon
logS10(-4.9) g/LALOGPS
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
Predicted Spectral Properties

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Withanolide,1TMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5OC56[C@@H](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@@]32C)C13821.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withanolide,1TMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@H]2CC[C@H]3[C@@H]4C[C@H]5OC56[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]6(C)[C@H]4CC[C@@]32C)C13792.6Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withanolide,2TMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5OC56[C@@H](O[Si](C)(C)C)C=CC(=O)[C@]6(C)[C@H]4CC[C@@]32C)C13758.5Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withanolide,1TBDMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5OC56[C@@H](O)C=CC(=O)[C@]6(C)[C@H]4CC[C@@]32C)C14037.4Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withanolide,1TBDMS,#2CC1=C(C)C(=O)O[C@@H]([C@](C)(O)[C@H]2CC[C@H]3[C@@H]4C[C@H]5OC56[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]6(C)[C@H]4CC[C@@]32C)C13998.0Semi standard non polarhttps://arxiv.org/abs/1905.12712
Withanolide,2TBDMS,#1CC1=C(C)C(=O)O[C@@H]([C@](C)(O[Si](C)(C)C(C)(C)C)[C@H]2CC[C@H]3[C@@H]4C[C@H]5OC56[C@@H](O[Si](C)(C)C(C)(C)C)C=CC(=O)[C@]6(C)[C@H]4CC[C@@]32C)C14213.9Semi standard non polarhttps://arxiv.org/abs/1905.12712
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Withanolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-1001-2139300000-7e60985d09b64f878a122017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withanolide GC-MS (2 TMS) - 70eV, Positivesplash10-0fdt-6019352000-44dbe9f9faffca66370e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Withanolide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 10V, Positive-QTOFsplash10-00di-0002900000-1f52202c63cf953f90782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 20V, Positive-QTOFsplash10-0udi-9026800000-7b1e1aaed10af48e838a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 40V, Positive-QTOFsplash10-0v00-5194100000-075f5c9753e4896a1d302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 10V, Negative-QTOFsplash10-014i-0001900000-876c22194e6f1a97bbd82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 20V, Negative-QTOFsplash10-0uxr-2728900000-64910a535ac954980abd2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 40V, Negative-QTOFsplash10-014i-9202000000-1a1334a54e34414dde7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 10V, Negative-QTOFsplash10-014i-0000900000-825df051d2576a60db7f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 20V, Negative-QTOFsplash10-014i-1003900000-d0175cc6da223a727be92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 40V, Negative-QTOFsplash10-015c-9303400000-c136a80072fdee60bade2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 10V, Positive-QTOFsplash10-00di-0003900000-0cf474e82baf6ca1efc02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 20V, Positive-QTOFsplash10-004i-5259600000-e46a909d3428f66c13932021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Withanolide 40V, Positive-QTOFsplash10-11ca-5196300000-3af868c3b54465fd160a2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB025194
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Khanna D, Sethi G, Ahn KS, Pandey MK, Kunnumakkara AB, Sung B, Aggarwal A, Aggarwal BB: Natural products as a gold mine for arthritis treatment. Curr Opin Pharmacol. 2007 Jun;7(3):344-51. Epub 2007 May 1. [PubMed:17475558 ]
  2. Begum VH, Sadique J: Long term effect of herbal drug Withania somnifera on adjuvant induced arthritis in rats. Indian J Exp Biol. 1988 Nov;26(11):877-82. [PubMed:3248848 ]
  3. Rasool M, Varalakshmi P: Suppressive effect of Withania somnifera root powder on experimental gouty arthritis: An in vivo and in vitro study. Chem Biol Interact. 2006 Dec 15;164(3):174-80. Epub 2006 Nov 7. [PubMed:17084827 ]