SCS-C002722
21,22-Diprenylpaxilline
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
571.8 Da
Threshold ≤ 500
ALogP
6.97
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
2 violations (MW, ALogP) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C37H49NO4
Molecular Weight:
571.8020 Da
SMILES:
CC(C)=CCc1cc2[nH]c3c(c2cc1CC=C(C)C)C[C@@H]1CC[C@@]2(O)C4=CC(=O)[C@@H](C(C)(C)O)O[C@H]4CC[C@]2(C)[C@@]31C
InChIKey:
YMPSZJNRZBHLRI-OGYDQXLWSA-N
InChI:
InChI=1S/C37H49NO4/c1-21(2)9-11-23-17-26-27-19-25-13-16-37(41)28-20-30(39)33(34(5,6)40)42-31(28)14-15-35(37,7)36(25,8)32(27)38-29(26)18-24(23)12-10-22(3)4/h9-10,17-18,20,25,31,33,38,40-41H,11-16,19H2,1-8H3/t25-,31-,33-,35+,36+,37+/m0/s1
Calculated Properties
ALogP:
6.974 lipophilicity
TPSA:
82.55 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
4
Rotatable Bonds:
5
Ring Count:
6
(2 aromatic)
Chiral Centers:
6
Fsp³:
0.5946 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002722
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.