Structure Database (LMSD)

H O H O O O O O O OH H
Common Name
Helvolic acid
Systematic Name
(4α,6β,8α,9β,13α,14β,16β,17β)-6,16- bis(acetyloxy)-3,7-dioxo-29-nordammara-1,17(20),24-trien-21-oic acid
Synonyms
LM ID
LMPR0106080005
Formula
C33H44O8
Exact Mass
Calculate m/z
568.30362
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C30 isoprenoids (triterpenes) [PR0106]
Prostostane and fusidane triterpenoids [PR010604]

String Representations

InChiKey (Click to copy)
MDFZYGLOIJNNRM-OAJDADRGSA-N
InChi (Click to copy)
InChI=1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1
SMILES (Click to copy)
C1=CC(=O)[C@@H](C)[C@]2([H])[C@H](OC(C)=O)C(=O)[C@@]3(C)[C@]([H])([C@]21C)CC[C@@]1([H])/C(=C(/C(O)=O)\CC/C=C(\C)/C)/[C@@H](OC(C)=O)C[C@@]13C

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Aspergillus fumigatus (#746128)
Eurotiomycetes (#147545)
Stereochemistry of helvolic acid.,
Tetrahedron Lett, 1967
Pubmed ID: 6046345

Other Databases

CHEBI ID
62460
PubChem CID
3002143
Cayman ID
21580
GuidePharm ID
12329

Calculated Physicochemical Properties

Heavy Atoms 41
Rings 4
Aromatic Rings 0
Rotatable Bonds 8
Van der Waals Molecular Volume 579.22
Topological Polar Surface Area 124.04
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 8
logP 5.97
Molar Refractivity 152.42

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Created at
-
Updated at
22nd Jul 2024