1.0 2011-09-21 00:25:03 UTC 2025-11-19 02:43:16 UTC FDB023125 Withanolide 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-&#954;B and NF-&#954;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] (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 C28H38O6 470.5977 470.266838948 (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 (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 30655-48-2 [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=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 SASUFNRGCZMRFD-LYOLWDNZSA-N 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. Withanolides and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroid lactones Aliphatic heteropolycyclic compounds 5,6-epoxysteroids Cyclohexenones Dialkyl ethers Dihydropyranones Enoate esters Epoxides Hydrocarbon derivatives Lactones Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Oxepanes Secondary alcohols Tertiary alcohols 5,6-epoxysteroid Alcohol Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclohexenone Dialkyl ether Dihydropyranone Enoate ester Ether Hydrocarbon derivative Ketone Lactone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Oxepane Oxirane Pyran Secondary alcohol Tertiary alcohol Withanolide-skeleton Solid logp 2.70 ALOGPS logs -4.91 ALOGPS solubility 5.77e-03 g/l ALOGPS logp 3.78 ChemAxon pka_strongest_acidic 13.28 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (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 ChemAxon average_mass 470.5977 ChemAxon mono_mass 470.266838948 ChemAxon 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 ChemAxon formula C28H38O6 ChemAxon 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 ChemAxon inchikey SASUFNRGCZMRFD-LYOLWDNZSA-N ChemAxon polar_surface_area 96.36 ChemAxon refractivity 126.87 ChemAxon polarizability 52.31 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 19988 Specdb::CMs 38545 Specdb::CMs 154526 Specdb::MsMs 310492 Specdb::MsMs 310493 Specdb::MsMs 310494 Specdb::MsMs 355222 Specdb::MsMs 355223 Specdb::MsMs 355224 Specdb::MsMs 2667289 Specdb::MsMs 2667290 Specdb::MsMs 2667291 Specdb::MsMs 3011972 Specdb::MsMs 3011973 Specdb::MsMs 3011974 HMDB03218 #<Reference:0x000055ce3364a6e8> #<Reference:0x000055ce3364a468> #<Reference:0x000055ce3364a210>