SCS-C001185

asperginulin A

Pathway: Alkaloids | Amino acids and Peptides Superclass: Peptide alkaloids

Chemical Structure

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Download: SDF SMILES

Source Information

Aspergillus sp. SK-28 (coral-derived fungus)

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

Beibu Gulf

DOI: 10.1021/acs.orglett.9b03796 · Organic Letters

Drug-likeness (Lipinski Ro5)

Molecular Weight

694.8 Da

Threshold ≤ 500

ALogP

5.41

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:

C42H42N6O4

Molecular Weight:

694.8000 Da

SMILES:

C=CC(C)(C)c1[nH]c2ccccc2c1C=C1NC(=O)[C@@]23[C@@H](CCN2C1=O)[C@@H]1CCN2C(=O)/C(=C/c4c(C(C)(C)C=C)[nH]c5ccccc45)NC(=O)[C@@]123

InChIKey:

                        QQFNACLTCVRIER-OIXDAEOXSA-N
                        
                    

InChI:

InChI=1S/C42H42N6O4/c1-7-39(3,4)33-25(23-13-9-11-15-29(23)43-33)21-31-35(49)47-19-17-27-28-18-20-48-36(50)32(46-38(52)42(28,48)41(27,47)37(51)45-31)22-26-24-14-10-12-16-30(24)44-34(26)40(5,6)8-2/h7-16,21-22,27-28,43-44H,1-2,17-20H2,3-6H3,(H,45,51)(H,46,52)/b31-21-,32-22?/t27-,28-,41+,42+/m0/s1

Calculated Properties

ALogP:

5.406 lipophilicity

TPSA:

130.40 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

9 (4 aromatic)

Chiral Centers:

Fsp³:

0.3333 fraction sp³ carbon

Database Information

Compound ID:

SCS-C001185

NPClassifier Pathway:

Alkaloids Amino acids and Peptides

NPClassifier Superclass:

Peptide alkaloids

NPClassifier Class:

N/A

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
Antifouling	inhibition_percent	barnacle Balanus reticulatus larvae	48.4 ± 0.6 %	10.1021/acs.orglett.9b03796 Organic Letters

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