SCS-C002719
(2S,4aR,4bR,6aS,12bS,12cS,14aS)-4a-demethylpaspaline-4a-carboxylic acid
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
5.20
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
1 violation (ALogP) — borderline drug-like
Chemical Properties
Molecular Formula:
C28H37NO4
Molecular Weight:
451.6070 Da
SMILES:
CC(C)(O)[C@@H]1CC[C@]2(C(=O)O)[C@H](CC[C@@]3(C)[C@H]2CC[C@H]2Cc4c([nH]c5ccccc45)[C@@]23C)O1
InChIKey:
QHCUDWQJVPGPRW-JKEWKBHPSA-N
InChI:
InChI=1S/C28H37NO4/c1-25(2,32)21-12-14-28(24(30)31)20-10-9-16-15-18-17-7-5-6-8-19(17)29-23(18)27(16,4)26(20,3)13-11-22(28)33-21/h5-8,16,20-22,29,32H,9-15H2,1-4H3,(H,30,31)/t16-,20+,21-,22-,26-,27+,28+/m0/s1
Calculated Properties
ALogP:
5.197 lipophilicity
TPSA:
82.55 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
3
Rotatable Bonds:
2
Ring Count:
6
(2 aromatic)
Chiral Centers:
7
Fsp³:
0.6786 fraction sp³ carbon
Database Information
Compound ID:
SCS-C002719
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.