SCS-C002589

penicilone B

Pathway: Polyketides Superclass: Chromanes Class: Azaphilones

Chemical Structure

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Source Information

Penicillium simplicissimum (NA)

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

Dongzhaigang

DOI: 10.1021/acs.jnatprod.6b01179 · Journal of Natural Products

Drug-likeness (Lipinski Ro5)

Molecular Weight

478.6 Da

Threshold ≤ 500

ALogP

5.89

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

1 violation (ALogP) — borderline drug-like

Chemical Properties

Molecular Formula:

C29H34O6

Molecular Weight:

478.5850 Da

SMILES:

CCCCCCC(C)/C=C(\C)C(=O)O[C@@]1(C)C(=O)C=C2C=C(c3c(C)cccc3O)OC=C2C1=O

InChIKey:

                        DJZXCCZVNHDZCQ-KKVDNXFESA-N
                        
                    

InChI:

InChI=1S/C29H34O6/c1-6-7-8-9-11-18(2)14-20(4)28(33)35-29(5)25(31)16-21-15-24(34-17-22(21)27(29)32)26-19(3)12-10-13-23(26)30/h10,12-18,30H,6-9,11H2,1-5H3/b20-14+/t18?,29-/m0/s1

Calculated Properties

ALogP:

5.888 lipophilicity

TPSA:

89.90 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.4138 fraction sp³ carbon

Database Information

Compound ID:

SCS-C002589

NPClassifier Pathway:

Polyketides

NPClassifier Superclass:

Chromanes

NPClassifier Class:

Azaphilones

Glycoside:

NPClassifier Status:

Classified

External Links:

General chemistry

PubChem ChemSpider ChEMBL

Natural product databases

COCONUT NP Atlas CMNPD: CMNPD29192

Biological Activity Data

No bioactivity data available for this compound.

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