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  3. 6-(5-(1-carboxy-4-N-carboxylate)-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one

SCS-C000524

6-(5-(1-carboxy-4-N-carboxylate)-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one

Pathway: Polyketides Superclass: Meroterpenoids | Cyclic polyketides Class: Phthalide derivatives | Tetraketide meroterpenoids
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Chemical Structure

Structure of 6-(5-(1-carboxy-4-N-carboxylate)-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one
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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.
Download: SDF SMILES

Source Information

Penicillium bialowiezense (coral-derived fungus)
Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species Penicillium bialowiezense
South China Sea
DOI: 10.3390/md16070230  · Marine Drugs

Drug-likeness (Lipinski Ro5)

Molecular Weight
405.4 Da
Threshold ≤ 500
ALogP
2.63
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
6
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C21H27NO7
Molecular Weight:
405.4000 Da
SMILES:
COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)NCCCC(=O)O)C(=O)OC2
InChIKey:
WZYZXNKYQQZNNV-UHFFFAOYSA-N
InChI:
InChI=1S/C21H27NO7/c1-12(7-9-16(23)22-10-4-5-17(24)25)6-8-14-19(26)18-15(11-29-21(18)27)13(2)20(14)28-3/h6,26H,4-5,7-11H2,1-3H3,(H,22,23)(H,24,25)
Calculated Properties
ALogP:
2.630 lipophilicity
TPSA:
122.16 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
6
Rotatable Bonds:
10
Ring Count:
2 (1 aromatic)
Chiral Centers:
0
Fsp³:
0.4762 fraction sp³ carbon

Database Information

Compound ID:
SCS-C000524
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Meroterpenoids Cyclic polyketides
NPClassifier Class:
Phthalide derivatives Tetraketide meroterpenoids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas

Biological Activity Data

Activity values are displayed only when a quantitative or clearly reported result is available. Tested organisms, cell lines and molecular targets are shown under Target / model.
Activity Assay Target / model Result Reference
Immunomodulatory / Anti-allergic IC50 IMPDH2 3.27–24.68 μM 10.3390/md16070230 Marine Drugs
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Structure enlarged