SCS-C002720
(2R,4bS,6aS,12bS,12cR,14aS)-2'-hydroxypaxilline
Pathway: Alkaloids | Terpenoids
Superclass: Tryptophan alkaloids
Class: Indole-Diterpenoid alkaloids (Penitrems)
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
Penicillium camemberti
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium camemberti
Wenchang
DOI:
10.1021/np400304q
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
451.6 Da
Threshold ≤ 500
ALogP
2.93
Threshold ≤ 5
H-Bond Donors
4
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H33NO5
Molecular Weight:
451.5630 Da
SMILES:
CC(O)(CO)[C@H]1O[C@H]2CC[C@@]3(C)[C@@](O)(CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)C2=CC1=O
InChIKey:
YCXQGKDLXRHABX-SUWUUCHZSA-N
InChI:
InChI=1S/C27H33NO5/c1-24(31,14-29)23-20(30)13-18-21(33-23)9-10-25(2)26(3)15(8-11-27(18,25)32)12-17-16-6-4-5-7-19(16)28-22(17)26/h4-7,13,15,21,23,28-29,31-32H,8-12,14H2,1-3H3/t15-,21-,23-,24?,25+,26+,27+/m0/s1
Calculated Properties
ALogP:
2.929 lipophilicity
TPSA:
102.78 Ų polar surface area
H-Bond Donors:
4
H-Bond Acceptors:
5
Rotatable Bonds:
2
Ring Count:
6
(2 aromatic)
Chiral Centers:
7
Fsp³:
0.5926 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002720
NPClassifier Pathway:
Alkaloids
Terpenoids
NPClassifier Superclass:
Tryptophan alkaloids
NPClassifier Class:
Indole-Diterpenoid alkaloids (Penitrems)
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.