SCS-C004863

penicacid B

Pathway: Polyketides Superclass: Cyclic polyketides Class: Phthalide derivatives Glycoside

Chemical Structure

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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/j.bmcl.2012.02.106 · Bioorganic & Medicinal Chemistry Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

498.5 Da

Threshold ≤ 500

ALogP

-0.47

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (HBD, HBA) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C23H30O12

Molecular Weight:

498.4810 Da

SMILES:

COc1c(C)c2c(c(O)c1C/C=C(\C)[C@H](CC(=O)O)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)OC2

InChIKey:

                        WYXRFIJAMXLLNA-YVWBRKQGSA-N
                        
                    

InChI:

InChI=1S/C23H30O12/c1-9(4-5-11-17(27)16-12(8-33-22(16)31)10(2)21(11)32-3)13(6-15(25)26)34-23-20(30)19(29)18(28)14(7-24)35-23/h4,13-14,18-20,23-24,27-30H,5-8H2,1-3H3,(H,25,26)/b9-4+/t13-,14+,18+,19-,20+,23-/m0/s1

Calculated Properties

ALogP:

-0.472 lipophilicity

TPSA:

192.44 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.5652 fraction sp³ carbon

Database Information

Compound ID:

SCS-C004863

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Cyclic polyketides

NPClassifier Class:

Phthalide derivatives

Glycoside:

Yes

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD22161

Biological Activity Data

No bioactivity data available for this compound.

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