SCS-C006863

maribasin A

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

1057.2 Da

Threshold ≤ 500

ALogP

-3.23

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:

C49H76N12O14

Molecular Weight:

1057.2170 Da

SMILES:

CC(C)CCCCCCCCC[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:

                        GOTAHJWMHYHCMJ-QELNVSPYSA-N
                        
                    

InChI:

InChI=1S/C49H76N12O14/c1-27(2)11-8-6-4-3-5-7-9-12-29-22-42(68)55-33(23-39(51)65)44(70)57-32(21-28-14-16-30(63)17-15-28)43(69)58-35(25-41(53)67)46(72)60-36(26-62)47(73)59-34(24-40(52)66)45(71)56-31(18-19-38(50)64)49(75)61-20-10-13-37(61)48(74)54-29/h14-17,27,29,31-37,62-63H,3-13,18-26H2,1-2H3,(H2,50,64)(H2,51,65)(H2,52,66)(H2,53,67)(H,54,74)(H,55,68)(H,56,71)(H,57,70)(H,58,69)(H,59,73)(H,60,72)/t29-,31+,32-,33-,34+,35-,36+,37-/m1/s1

Calculated Properties

ALogP:

-3.226 lipophilicity

TPSA:

436.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.6327 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006863

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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