SCS-C002759
21-epi-ophiobolin O
Pathway: Terpenoids
Superclass: Sesterterpenoids
Class: Ophiobolane sesterterpenoids
Glycoside
Chemical Structure
Loading 3D structure...
3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Aspergillus ustus
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Aspergillus
Species
Aspergillus ustus
Wenchang
DOI:
10.1021/acs.jnatprod.7b00335
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
430.6 Da
Threshold ≤ 500
ALogP
5.63
Threshold ≤ 5
H-Bond Donors
1
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C27H42O4
Molecular Weight:
430.6290 Da
SMILES:
CO[C@@H]1O[C@@]2(OC)C[C@@](C)(O)[C@H]3C[C@@]4(C)CC[C@H]([C@@H](C)/C=C\C=C(C)C)[C@@H]4C/C=C/1[C@H]32
InChIKey:
IJDXBTKKTDHRMD-ASGAXXHNSA-N
InChI:
InChI=1S/C27H42O4/c1-17(2)9-8-10-18(3)19-13-14-25(4)15-22-23-20(11-12-21(19)25)24(29-6)31-27(23,30-7)16-26(22,5)28/h8-11,18-19,21-24,28H,12-16H2,1-7H3/b10-8-,20-11+/t18-,19+,21-,22-,23+,24+,25+,26+,27-/m0/s1
Calculated Properties
ALogP:
5.630 lipophilicity
TPSA:
47.92 Ų polar surface area
H-Bond Donors:
1
H-Bond Acceptors:
4
Rotatable Bonds:
5
Ring Count:
4
(0 aromatic)
Chiral Centers:
9
Fsp³:
0.7778 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002759
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Sesterterpenoids
NPClassifier Class:
Ophiobolane sesterterpenoids
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.