SCS-C004585

aspergilone B

Pathway: Polyketides Superclass: Chromanes Class: Azaphilones

Chemical Structure

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Source Information

Aspergillus sp. (coral-derived fungus)

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

South China Sea

DOI: 10.1016/j.bmcl.2010.12.005 · Bioorganic & Medicinal Chemistry Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

604.7 Da

Threshold ≤ 500

ALogP

6.65

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:

C39H40O6

Molecular Weight:

604.7430 Da

SMILES:

CC1=C2C(=CO[C@@H](C)[C@@H]2C)C(=O)[C@@](Cc2ccccc2)(C[C@]2(Cc3ccccc3)C(=O)C3=CO[C@@H](C)[C@H](C)C3=C(C)C2=O)C1=O

InChIKey:

                        ZABFMNJNXWCHSA-KSGLQAFKSA-N
                        
                    

InChI:

InChI=1S/C39H40O6/c1-22-26(5)44-19-30-32(22)24(3)34(40)38(36(30)42,17-28-13-9-7-10-14-28)21-39(18-29-15-11-8-12-16-29)35(41)25(4)33-23(2)27(6)45-20-31(33)37(39)43/h7-16,19-20,22-23,26-27H,17-18,21H2,1-6H3/t22-,23-,26-,27-,38-,39-/m0/s1

Calculated Properties

ALogP:

6.649 lipophilicity

TPSA:

86.74 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (2 aromatic)

Chiral Centers:

Fsp³:

0.3846 fraction sp³ carbon

Database Information

Compound ID:

SCS-C004585

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: CMNPD20831

Biological Activity Data

No bioactivity data available for this compound.

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