Structure Database (LMSD)

Common Name
Gracilosulfate C
Systematic Name
4β,23S-dihydroxy,5β,6β-epoxy-cholest-3β-yl-sulfate
Synonyms
LM ID
LMST05020054
Status
Active
Exact Mass
Calculate m/z
514.296427
Formula
C27H46O7S
Abbrev
ST 27:1;O4;S
Show lipids differing only in stereochemistry/bond geometry
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Main

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Steroid conjugates [ST05]
Sulfates [ST0502]

String Representations

InChiKey (Click to copy)
HMBXCOGSOICQBC-ONRXLPROSA-N
InChi (Click to copy)
InChI=1S/C27H46O7S/c1-15(2)12-17(28)13-16(3)19-6-7-20-18-14-23-27(33-23)24(29)22(34-35(30,31)32)9-11-26(27,5)21(18)8-10-25(19,20)4/h15-24,28-29H,6-14H2,1-5H3,(H,30,31,32)/t16-,17+,18+,19-,20+,21+,22+,23-,24+,25-,26-,27+/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)CC(C)C)[C@@]4(C)CC[C@]2([H])[C@@]13C

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

Calculated Physicochemical Properties

Heavy Atoms 35
Rings 5
Aromatic Rings 0
Rotatable Bonds 7
Van der Waals Molecular Volume 493.90
Topological Polar Surface Area 116.59
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 7
logP 7.05
Molar Refractivity 134.24

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