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  3. 6-(5-(2,3-dihydroxy-1-carboxyglyceride)-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one

SCS-C000523

6-(5-(2,3-dihydroxy-1-carboxyglyceride)-3-methylpent-2-enyl)-7-hydroxy-5-methoxy-4-methylphthalan-1-one

Pathway: Polyketides Superclass: Cyclic polyketides Class: Phthalide derivatives
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Chemical Structure

Structure of 6-(5-(2,3-dihydroxy-1-carboxyglyceride)-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
394.4 Da
Threshold ≤ 500
ALogP
1.54
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
8
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C20H26O8
Molecular Weight:
394.4000 Da
SMILES:
COc1c(C)c2c(c(O)c1CC=C(C)CCC(=O)OCC(O)CO)C(=O)OC2
InChIKey:
AGANHPVGHKGEKN-UHFFFAOYSA-N
InChI:
InChI=1S/C20H26O8/c1-11(5-7-16(23)27-9-13(22)8-21)4-6-14-18(24)17-15(10-28-20(17)25)12(2)19(14)26-3/h4,13,21-22,24H,5-10H2,1-3H3
Calculated Properties
ALogP:
1.545 lipophilicity
TPSA:
122.52 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
8
Rotatable Bonds:
9
Ring Count:
2 (1 aromatic)
Chiral Centers:
1
Fsp³:
0.5000 fraction sp³ carbon

Database Information

Compound ID:
SCS-C000523
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Cyclic polyketides
NPClassifier Class:
Phthalide derivatives
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