Withanolide
PubChem CID: 53477765
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| Compound Synonyms | withanolide, (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[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one, LMST01160018, 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate, 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate, (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid delta-lactone |
|---|---|
| Topological Polar Surface Area | 96.4 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 34.0 |
| 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-κ, B and NF-κ, B-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] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 1030.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 10.0 |
| Iupac 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 |
| Prediction Hob | 0.0 |
| Xlogp | 3.1 |
| Molecular Formula | C28H38O6 |
| Prediction Swissadme | 1.0 |
| Inchi Key | SASUFNRGCZMRFD-LYOLWDNZSA-N |
| Fcsp3 | 0.7857142857142857 |
| Logs | -4.616 |
| Rotatable Bond Count | 2.0 |
| State | Solid |
| Logd | 3.716 |
| Synonyms | (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate, (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, (4beta,5beta,6beta,22R)-5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid delta-lactone, 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oate, 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid, 5,6-Epoxy-4,20,22-trihydroxy-1-oxoergosta-2,24-dien-26-oic acid delta-lactone |
| Compound Name | Withanolide |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 470.267 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 470.267 |
| Hydrogen Bond Acceptor Count | 6.0 |
| Molecular Weight | 470.6 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 11.0 |
| Total Bond Stereocenter Count | 0.0 |
| Esol | -4.591357200000003 |
| Inchi | 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 |
| Smiles | CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3C[C@@H]5C6([C@@]4(C(=O)C=C[C@@H]6O)C)O5)C)O)C |
| Nring | 6.0 |
| Defined Bond Stereocenter Count | 0.0 |
- 1. Outgoing r'ship
FOUND_INto/from Solanum Torvum (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all