Structure database (LMSD)

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LM IDLMST05050012
Common NameEvasterioside A
Systematic Name(25S)-3β-(β-D-xylopyranosyloxy)-6β,8,15α-trihydroxy-5α-campest-22E-en-26-yl
sulfate
Synonyms(20R,22E,24R,25S)-3-O-(β-D-xylopyranosyl)-24-methyl-5α-cholest-22-ene-3β,6β,
8,15α,26-pentol 26-sulfate
Exact Mass
676.3493 (neutral)    Calculate m/z:
FormulaC33H56O12S
CategorySterol Lipids [ST]
Main ClassSteroid conjugates [ST05]
Sub ClassOther Steroid conjugates [ST0505]
PubChem CID52931564
InChIKeyYWTLHWYRVSPWOJ-ZVCZZSFPSA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C33H56O12S/c1-17(19(3)15-44-46(40,41)42)6-7-18(2)21-13-23(34)29-32(21,5)11-9-26-31(4)10-8-20(12-22(31)24(35)14-33(26,29)39)45-30-28(38)27(37)25(36)16-43-30/h6-7,17-30,34-39H,8-16H2,1-5H3,(H,40,41,42)/b7-6+/t17-,18-,19-,20+,21-,22-,23+,24-,25-,26-,27+,28-,29-,30+,31+,32-,33+/m1/s1
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SMILES
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@@H](C)[C@@H](COS(O)(=O)=O)C)C[C@H](O)[C@@]4([H])[C@]3(O)C[C@@H](O)[C@@]2([H])C[C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C1
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StatusActive
ReferencesEvasteriosides A and B and other sulfated steroids from the Pacific starfish Evasterias retifera
Russian Chemical Bulletin 2008
DOI: https://doi.org/10.1007/s11172-008-0347-6

Marine natural products
John W. Blunt, Brent R. Copp, Murray H. G. Munro,
Peter T. Northcote and Michele R. Prinsep
Nat. Prod. Rep., 2011, 28, 196-268
Calculated physicochemical properties (?):
 Heavy Atoms46Rings5Aromatic Rings0Rotatable Bonds9
 van der Waals
Molecular Volume
639.01Topological Polar
Surface Area
205.51Hydrogen
Bond Donors
7Hydrogen
Bond Acceptors
12
 logP5.92Molar
Refractivity
171.21