1.0 2016-09-30 23:03:09 UTC 2020-04-22 15:11:50 UTC BMDB0003218 BMDB03218 Withanolide C28H38O6 470.606 470.266838944 (1S,2R,6S,7R,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 (1S,2R,6S,7R,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[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one [H]C12C[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)[C@@]13O2 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-MOUTUSPFSA-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. Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroid lactones Withanolides and derivatives 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 Aliphatic heteropolycyclic compounds Solid logp 2.70 ALOGPS logs -4.91 ALOGPS logp 3.78 ChemAxon pka_strongest_acidic 13.28 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac (1S,2R,6S,7R,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 ChemAxon average_mass 470.606 ChemAxon mono_mass 470.266838944 ChemAxon smiles [H]C12C[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)[C@@]13O2 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-MOUTUSPFSA-N ChemAxon polar_surface_area 96.36 ChemAxon refractivity 126.87 ChemAxon polarizability 51.23 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 6 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::MsMs 1262815 Specdb::MsMs 1262816 Specdb::MsMs 1262817 Specdb::MsMs 1377916 Specdb::MsMs 1377917 Specdb::MsMs 1377918 Withanolide