Structure Database (LMSD)

Common Name
Penicisteroid B
Systematic Name
16β-acetoxy-ergosta-5,22E-dien-3β,7β-diol
Synonyms
  • 16beta-acetoxy-3beta,7beta-dihydroxyergost-5,22E-diene
LM ID
LMST01031171
Formula
C30H48O4
Exact Mass
Calculate m/z
472.35526
Sum Composition
ST 30:3;O4
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Sterol Lipids [ST]
Sterols [ST01]
Ergosterols and C24-methyl derivatives [ST0103]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Penicillium chrysogenum (#5076)
Eurotiomycetes (#147545)
Penicisteroids A and B, antifungal and cytotoxic polyoxygenated steroids from the marine alga-derived endophytic fungus Penicillium chrysogenum QEN-24S.,
Bioorg Med Chem Lett, 2011
Pubmed ID: 21489788

String Representations

InChiKey (Click to copy)
ASJDHPNJTXZGII-ZVMPSDJMSA-N
InChi (Click to copy)
InChI=1S/C30H48O4/c1-17(2)18(3)8-9-19(4)27-26(34-20(5)31)15-24-23-11-10-21-14-22(32)12-13-29(21,6)28(23)25(33)16-30(24,27)7/h8-10,17-19,22-28,32-33H,11-16H2,1-7H3/b9-8+/t18-,19+,22-,23-,24-,25-,26-,27-,28+,29-,30-/m0/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])[C@@H](O)C[C@]4(C)[C@@]([H])([C@]([H])(C)/C=C/[C@H](C)C(C)C)[C@@H](OC(C)=O)C[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Other Databases

PubChem CID
139588208

Calculated Physicochemical Properties

Heavy Atoms 34
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 505.36
Topological Polar Surface Area 66.76
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 6.78
Molar Refractivity 137.37

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Created at
26th Feb 2021
Updated at
26th Feb 2021