Structure Database (LMSD)

Common Name
Gracilosulfate A
Systematic Name
4β,23R-dihydroxy,5β,6β-epoxy-campest-3β-yl-sulfate
Synonyms
  • 4beta,23R-dihydroxy-5beta,6beta-epoxy-24S-methylcholest-3beta-yl sulfate
LM ID
LMST05020052
Formula
C28H48O7S
Exact Mass
Calculate m/z
528.312077
Sum Composition
ST 28:1;O4;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]
Ergosterols and C24-methyl derivatives [ST0103]

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)
NVMMLEGZPRKADO-KCLFOZORSA-N
InChi (Click to copy)
InChI=1S/C28H48O7S/c1-15(2)17(4)22(29)13-16(3)19-7-8-20-18-14-24-28(34-24)25(30)23(35-36(31,32)33)10-12-27(28,6)21(18)9-11-26(19,20)5/h15-25,29-30H,7-14H2,1-6H3,(H,31,32,33)/t16-,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])CC[C@H]([C@H](C)C[C@@H](O)[C@@H](C)C(C)C)[C@@]4(C)CC[C@]2([H])[C@@]13C

Other Databases

PubChem CID
171037425

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 5
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 511.20
Topological Polar Surface Area 116.59
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 7.30
Molar Refractivity 138.78

Admin

Created at
12th Oct 2020
Updated at
12th Oct 2020