Structure Database (LMSD)

Common Name
12beta,15beta,25,28-tetrahydroxyergone
Systematic Name
12β,15β,25,28-tetrahydroxyergosta-4,6,8(14),22-tetraen-3-one
Synonyms
LM ID
LMST01031357
Formula
C28H40O5
Exact Mass
Calculate m/z
456.287575
Sum Composition
ST 28:5;O5
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
Aspergillus terreus (#33178)
Eurotiomycetes (#147545)
Ergone Derivatives from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10 and 25,28-Dihydroxyergone-Induced Apoptosis in Human Colon Cancer SW620 Cells.,
J Nat Prod, 2024
Pubmed ID: 38856635

String Representations

InChiKey (Click to copy)
XJROYMDLDCJXJR-JNLPXLSFSA-N
InChi (Click to copy)
InChI=1S/C28H40O5/c1-16(6-7-18(15-29)26(2,3)33)21-13-23(31)25-20-9-8-17-12-19(30)10-11-27(17,4)22(20)14-24(32)28(21,25)5/h6-9,12,16,18,21-24,29,31-33H,10-11,13-15H2,1-5H3/b7-6+/t16-,18-,21-,22+,23-,24-,27+,28+/m1/s1
SMILES (Click to copy)
C1CC(=O)C=C2C=CC3=C4[C@H](O)C[C@]([H])([C@H](C)/C=C/[C@H](CO)C(O)(C)C)[C@@]4(C)[C@H](O)C[C@]3([H])[C@@]12C

Calculated Physicochemical Properties

Heavy Atoms 33
Rings 4
Aromatic Rings
Rotatable Bonds 5
Van der Waals Molecular Volume 474.27
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 4.63
Molar Refractivity 130.14

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Created at
25th Jun 2024
Updated at
25th Jun 2024