SCS-C005575
peniisocoumarin A
Pathway: Shikimates and Phenylpropanoids
Superclass: Coumarins
Class: Isocoumarins
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 commune
(fungus)
Kingdom
Fungi
Phylum
Ascomycota
Class
Eurotiomycetes
Order
Eurotiales
Family
Aspergillaceae
Genus
Penicillium
Species
Penicillium commune
Qi'ao Mangrove Nature Reserve
DOI:
10.1021/acs.jnatprod.7b01018
· Journal of Natural Products
Drug-likeness (Lipinski Ro5)
Molecular Weight
552.5 Da
Threshold ≤ 500
ALogP
2.79
Threshold ≤ 5
H-Bond Donors
2
Threshold ≤ 5
H-Bond Acceptors
12
Threshold ≤ 10
2 violations (MW, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C28H24O12
Molecular Weight:
552.4880 Da
SMILES:
COC(=O)[C@@H]1[C@H](C(=O)OC)[C@@H](c2cc3cc(OC)cc(O)c3c(=O)o2)[C@H]1c1cc2cc(OC)cc(O)c2c(=O)o1
InChIKey:
CVKPNDGDFOIINI-NVPYSNMXSA-N
InChI:
InChI=1S/C28H24O12/c1-35-13-5-11-7-17(39-27(33)19(11)15(29)9-13)21-22(24(26(32)38-4)23(21)25(31)37-3)18-8-12-6-14(36-2)10-16(30)20(12)28(34)40-18/h5-10,21-24,29-30H,1-4H3/t21-,22+,23+,24-
Calculated Properties
ALogP:
2.787 lipophilicity
TPSA:
171.94 Ų polar surface area
H-Bond Donors:
2
H-Bond Acceptors:
12
Rotatable Bonds:
6
Ring Count:
5
(4 aromatic)
Chiral Centers:
4
Fsp³:
0.2857 fraction sp³ carbon
Database Information
Compound ID:
SCS-C005575
NPClassifier Pathway:
Shikimates and Phenylpropanoids
NPClassifier Superclass:
Coumarins
NPClassifier Class:
Isocoumarins
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
Biological Activity Data
No bioactivity data available for this compound.