SCS-C007442
brefeldindole C
Pathway: Alkaloids | Terpenoids
Superclass: Tryptophan alkaloids
Class: Indole-Diterpenoid alkaloids (Penitrems)
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
Penicillium brefeldianum GXIMD 02511
(NA)
Original source name: Penicillium brefeldianum | Penicillium brefeldianum GXIMD 02511
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium brefeldianum
South China Sea
DOI:
10.1021/acs.jnatprod.5c00425
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
537.7 Da
Threshold ≤ 500
ALogP
3.98
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
1 violation (MW) — borderline drug-like
Chemical Properties
Molecular Formula:
C32H43NO6
Molecular Weight:
537.6970 Da
SMILES:
CC(C)(O)CCc1cccc2[nH]c3c(c12)C[C@@H]1CC[C@@]2(O)C4=CC(=O)[C@@H](C(C)(C)O)O[C@@]4(O)CC[C@]2(C)[C@@]31C
InChIKey:
BDXKDERGEHCFDP-SDPXOEJRSA-N
InChI:
InChI=1S/C32H43NO6/c1-27(2,35)12-10-18-8-7-9-21-24(18)20-16-19-11-13-31(37)23-17-22(34)26(28(3,4)36)39-32(23,38)15-14-29(31,5)30(19,6)25(20)33-21/h7-9,17,19,26,33,35-38H,10-16H2,1-6H3/t19-,26-,29+,30+,31+,32-/m0/s1
Calculated Properties
ALogP:
3.980 lipophilicity
TPSA:
123.01 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
6
Rotatable Bonds:
4
Ring Count:
6
(2 aromatic)
Chiral Centers:
6
Fsp³:
0.6562 fraction sp³ carbon
Database Information
Compound ID:
SCS-C007442
NPClassifier Pathway:
Alkaloids
Terpenoids
NPClassifier Superclass:
Tryptophan alkaloids
NPClassifier Class:
Indole-Diterpenoid alkaloids (Penitrems)
Glycoside:
Yes
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.