Structure Database (LMSD)

Common Name
Gracilosulfate E
Systematic Name
4β,15β,23R-trihydroxy,5β,6β-epoxy-24-methylenecholest-3β-yl sulfate
Synonyms
LM ID
LMST05020056
Formula
C28H46O8S
Exact Mass
Calculate m/z
542.291342
Sum Composition
ST 28:2;O5;S
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroid conjugates [ST05]
Sulfates [ST0502]
Sterols [ST01]
Cholesterol and derivatives [ST0101]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Haliclona (#6057)
Demospongiae (#6042)
Gracilosulfates A-G, Monosulfated Polyoxygenated Steroids from the Marine Sponge Haliclona gracilis.,
Mar Drugs, 2020
Pubmed ID: 32872590

String Representations

InChiKey (Click to copy)
QVNUGLCWTMLSGH-ZUHDTBAESA-N
InChi (Click to copy)
InChI=1S/C28H46O8S/c1-14(2)16(4)20(29)11-15(3)19-13-21(30)24-17-12-23-28(35-23)25(31)22(36-37(32,33)34)8-10-27(28,6)18(17)7-9-26(19,24)5/h14-15,17-25,29-31H,4,7-13H2,1-3,5-6H3,(H,32,33,34)/t15-,17-,18+,19-,20-,21-,22+,23-,24-,25+,26-,27-,28+/m1/s1
SMILES (Click to copy)
C1C[C@H](OS(O)(=O)=O)[C@H](O)[C@@]23O[C@@H]2C[C@@]2([H])[C@]4([H])[C@H](O)C[C@H]([C@H](C)C[C@@H](O)C(=C)C(C)C)[C@@]4(C)CC[C@]2([H])[C@@]13C

Other Databases

PubChem CID
171120305

Calculated Physicochemical Properties

Heavy Atoms 37
Rings 5
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 517.35
Topological Polar Surface Area 136.82
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 8
logP 6.48
Molar Refractivity 140.66

Admin

Created at
12th Oct 2020
Updated at
17th Sep 2024