SCS-C008330
(3S,4R,5S)-4-((3E,5E)-hepta-3,5-dien-1-yl)-4-hydroxy-5-(hydroxymethyl)-3-methyl-1-azabicyclo[3.3.0]octan-2-one
Pathway: Alkaloids
Superclass: Lysine alkaloids
Class: Indolizidine alkaloids
Chemical Structure
![Structure of (3S,4R,5S)-4-((3E,5E)-hepta-3,5-dien-1-yl)-4-hydroxy-5-(hydroxymethyl)-3-methyl-1-azabicyclo[3.3.0]octan-2-one](/scsmarinenp/static/images/structures/SCS-C008330.png)
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
Source Information
Penicillium citrinum
(NA)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium citrinum
South China Sea
DOI:
10.1021/acs.jafc.5c15871
· Journal of Agricultural and Food Chemistry
Drug-likeness (Lipinski Ro5)
Molecular Weight
279.4 Da
Threshold ≤ 500
ALogP
1.63
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
3
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate
Chemical Properties
Molecular Formula:
C16H25NO3
Molecular Weight:
279.3800 Da
SMILES:
C/C=C/C=C/CC[C@@]1(O)[C@H](C)C(=O)N2CCC[C@@]21CO
InChIKey:
QNZNUVSFGWAZBQ-QCVUQLRASA-N
InChI:
InChI=1S/C16H25NO3/c1-3-4-5-6-7-10-16(20)13(2)14(19)17-11-8-9-15(16,17)12-18/h3-6,13,18,20H,7-12H2,1-2H3/b4-3+,6-5+/t13-,15+,16-/m1/s1
Calculated Properties
ALogP:
1.633 lipophilicity
TPSA:
60.77 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
3
Rotatable Bonds:
5
Ring Count:
2
(0 aromatic)
Chiral Centers:
3
Fsp³:
0.6875 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008330
NPClassifier Pathway:
Alkaloids
NPClassifier Superclass:
Lysine alkaloids
NPClassifier Class:
Indolizidine alkaloids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.