SCS-C007295

(S)-6,8-dihydroxy-5-(methoxymethyl)-3,7-dimethyl isochroman-1-one

Pathway: Shikimates and Phenylpropanoids Superclass: Coumarins Class: Isocoumarins

Chemical Structure

Structure of (S)-6,8-dihydroxy-5-(methoxymethyl)-3,7-dimethyl isochroman-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.

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Source Information

Penicillium sp. (soft coral-derived fungus)

Kingdom Fungi Phylum Ascomycota Class Eurotiomycetes Order Eurotiales Family Aspergillaceae Genus Penicillium Species NA

South China Sea

DOI: 10.1016/s1875-5364(20)30031-5 · Chinese Journal of Natural Medicines

Drug-likeness (Lipinski Ro5)

Molecular Weight

252.3 Da

Threshold ≤ 500

ALogP

1.65

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:

C13H16O5

Molecular Weight:

252.2660 Da

SMILES:

COCc1c(O)c(C)c(O)c2c1CC(C)OC2=O

InChIKey:

                        CTMUQISKNVTCBS-UHFFFAOYSA-N
                        
                    

InChI:

InChI=1S/C13H16O5/c1-6-4-8-9(5-17-3)11(14)7(2)12(15)10(8)13(16)18-6/h6,14-15H,4-5H2,1-3H3

Calculated Properties

ALogP:

1.654 lipophilicity

TPSA:

75.99 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

2 (1 aromatic)

Chiral Centers:

Fsp³:

0.4615 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007295

NPClassifier Pathway:

Shikimates and Phenylpropanoids

NPClassifier Superclass:

Coumarins

NPClassifier Class:

Isocoumarins

Glycoside:

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
Enzyme inhibition	—	α-glucosidase	Compounds 1 and 2 exhibited weak inhibitory activity against α-glucosidase.	10.1016/s1875-5364(20)30031-5 Chinese Journal of Natural Medicines

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