SCS-C006857

maribasin D

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: Cyclic peptides

Chemical Structure

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Download: SDF SMILES

Source Information

Aspergillus sp. SCSIO 41501 (coral-derived fungus)

Original source name: Aspergillus sp. SCSIO 41501 (Trichocomaceae), isolated from Melitodes squamata Nutting (Melithaidae)

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

Offshore Hainan Island · ~18°11'N, 109°25'E

DOI: 10.1016/j.phytochem.2021.112967 · Phytochemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

1071.2 Da

Threshold ≤ 500

ALogP

-2.69

Threshold ≤ 5

H-Bond Donors

Threshold ≤ 5

H-Bond Acceptors

Threshold ≤ 10

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

Chemical Properties

Molecular Formula:

C50H78N12O14

Molecular Weight:

1071.2440 Da

SMILES:

CCCCCCCCCCCCC[C@@H]1CC(=O)N[C@H](CC(N)=O)C(=O)N[C@H](Cc2ccc(O)cc2)C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N2CCC[C@@H]2C(=O)N1

InChIKey:

                        RYWWJAWUGBUTQG-HICGOCBBSA-N
                        
                    

InChI:

InChI=1S/C50H78N12O14/c1-2-3-4-5-6-7-8-9-10-11-12-14-30-24-43(69)56-34(25-40(52)66)45(71)58-33(23-29-16-18-31(64)19-17-29)44(70)59-36(27-42(54)68)47(73)61-37(28-63)48(74)60-35(26-41(53)67)46(72)57-32(20-21-39(51)65)50(76)62-22-13-15-38(62)49(75)55-30/h16-19,30,32-38,63-64H,2-15,20-28H2,1H3,(H2,51,65)(H2,52,66)(H2,53,67)(H2,54,68)(H,55,75)(H,56,69)(H,57,72)(H,58,71)(H,59,70)(H,60,74)(H,61,73)/t30-,32+,33-,34-,35+,36-,37+,38-/m1/s1

Calculated Properties

ALogP:

-2.692 lipophilicity

TPSA:

436.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.6400 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006857

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Cyclic peptides

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
Antifungal	MIC	Alternaria solani, Curvularia australiensis, Colletotrichum gloeosporioiles, Fusarium oxysporum, Pyricularia oryzae	3.12–50.0 μg/disc	10.1016/j.phytochem.2021.112967 Phytochemistry

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