SCS-C002646

penicilone D

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

513.0 Da

Threshold ≤ 500

ALogP

6.46

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

2 violations (MW, ALogP) — not drug-like by Ro5

Chemical Properties

Molecular Formula:

C29H33ClO6

Molecular Weight:

513.0300 Da

SMILES:

CCCCCCC(C)/C=C(\C)C(=O)O[C@@]1(C)C(=O)C2=COC(c3c(C)cccc3O)=CC2=C(Cl)C1=O

InChIKey:

                        VBEXROICVMHLSP-ZFJKLULRSA-N
                        
                    

InChI:

InChI=1S/C29H33ClO6/c1-6-7-8-9-11-17(2)14-19(4)28(34)36-29(5)26(32)21-16-35-23(15-20(21)25(30)27(29)33)24-18(3)12-10-13-22(24)31/h10,12-17,31H,6-9,11H2,1-5H3/b19-14+/t17?,29-/m0/s1

Calculated Properties

ALogP:

6.455 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-C002646

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: CMNPD29194

Biological Activity Data

No bioactivity data available for this compound.

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