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Bovine Metabolome Database



Showing metabocard for Withanolide (BMDB03218)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2006-05-22 16:12:42
Update Date 2009-05-05 20:59:39
Accession Number BMDB03218
Common Name Withanolide
Description Withanolides, 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)
Synonyms
  1. 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid delta-lactone
  2. (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid delta-lactone
  3. 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate
  4. (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate
  5. 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid
  6. (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid
Chemical IUPAC Name Not Available
Chemical Formula C28H38O6
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Cholesterols and derivatives
Class
  • Steroids and Steroid Derivatives
Sub Class
  • Ketosteroids
Family
  • Mammalian_Metabolite
Species
  • ketone; secondary alcohol; tertiary alcohol; dialkyl ether; carboxylic acid ester; lactone; alkene; heterocyclic compound
Biofunction
  • Hormones, Membrane component
Application
Source
  • Exogenous
Average Molecular Weight 470.598
Monoisotopic Molecular Weight 470.266846
Isomeric SMILES CC1=C(C)C(=O)O[C@H](C1)[C@](C)(O)[C@H]1CC[C@H]2[C@@H]3C[C@H]4OC44[C@@H](O)C=CC(=O)[C@]4(C)[C@H]3CC[C@]12C
Canonical SMILES CC1=C(C)C(=O)OC(C1)C(C)(O)C1CCC2C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C
KEGG Compound ID C08842 Link Image
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 161671 Link Image
PubChem Substance 10254548 Link Image
ChEBI ID Not Available
CAS Registry Number 30655-48-2
InChI Identifier InChI=1/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
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 5.77e-03 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge Not Available
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity 3.2 [Predicted by PubChem via XLOGP]; 2.70 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References Not Available