Structure Database (LMSD)

Common Name
Penicisteroid A
Systematic Name
16β-acetoxy-5α-ergosta-22E-en-3β,,6β,7β,11β,tetraol
Synonyms
  • 16beta-acetoxy-3beta,,6beta,7beta,11beta-tetrahydroxy-5alpha-ergost-22E-diene
LM ID
LMST01031170
Formula
C30H50O6
Exact Mass
Calculate m/z
506.36074
Sum Composition
ST 30:2;O6
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)
VXYHQHOVSPABTG-KJYRXAALSA-N
InChi (Click to copy)
InChI=1S/C30H50O6/c1-15(2)16(3)8-9-17(4)25-23(36-18(5)31)13-20-24-26(22(33)14-30(20,25)7)29(6)11-10-19(32)12-21(29)27(34)28(24)35/h8-9,15-17,19-28,32-35H,10-14H2,1-7H3/b9-8+/t16-,17+,19-,20-,21+,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])[C@@H](O)[C@@H](O)[C@@]2([H])C[C@@H](O)C1

Other Databases

PubChem CID
54581889

Calculated Physicochemical Properties

Heavy Atoms 36
Rings 4
Aromatic Rings 0
Rotatable Bonds 6
Van der Waals Molecular Volume 525.58
Topological Polar Surface Area 107.22
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 6
logP 5.38
Molar Refractivity 141.20

Admin

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