SCS-C002721
(2S,3R,4R,4aS,4bR,6aS,12bS,12cS,14aS)-4a-demethylpaspaline-3,4,4a-triol
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
455.6 Da
Threshold ≤ 500
ALogP
2.80
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
5
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C27H37NO5
Molecular Weight:
455.5950 Da
SMILES:
CC(C)(O)[C@H]1O[C@H]2CC[C@@]3(C)[C@@H](CC[C@H]4Cc5c([nH]c6ccccc56)[C@@]43C)[C@]2(O)[C@H](O)[C@H]1O
InChIKey:
LQDPZVYIZKOAPV-BCHUPDFZSA-N
InChI:
InChI=1S/C27H37NO5/c1-24(2,31)23-20(29)22(30)27(32)18-10-9-14-13-16-15-7-5-6-8-17(15)28-21(16)26(14,4)25(18,3)12-11-19(27)33-23/h5-8,14,18-20,22-23,28-32H,9-13H2,1-4H3/t14-,18+,19-,20+,22+,23-,25-,26+,27+/m0/s1
Calculated Properties
ALogP:
2.799 lipophilicity
TPSA:
105.94 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
5
Rotatable Bonds:
1
Ring Count:
6
(2 aromatic)
Chiral Centers:
9
Fsp³:
0.7037 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002721
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.