SCS-C006858

maribasin E

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

Chemical Structure

Loading 3D structure...

3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.

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

1085.3 Da

Threshold ≤ 500

ALogP

-2.45

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:

C51H80N12O14

Molecular Weight:

1085.2710 Da

SMILES:

CCC(C)CCCCCCCCCC[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:

                        YRVATLGHUYNELF-MOKNKRSMSA-N
                        
                    

InChI:

InChI=1S/C51H80N12O14/c1-3-29(2)13-10-8-6-4-5-7-9-11-14-31-24-44(70)57-35(25-41(53)67)46(72)59-34(23-30-16-18-32(65)19-17-30)45(71)60-37(27-43(55)69)48(74)62-38(28-64)49(75)61-36(26-42(54)68)47(73)58-33(20-21-40(52)66)51(77)63-22-12-15-39(63)50(76)56-31/h16-19,29,31,33-39,64-65H,3-15,20-28H2,1-2H3,(H2,52,66)(H2,53,67)(H2,54,68)(H2,55,69)(H,56,76)(H,57,70)(H,58,73)(H,59,72)(H,60,71)(H,61,75)(H,62,74)/t29?,31-,33+,34-,35-,36+,37-,38+,39-/m1/s1

Calculated Properties

ALogP:

-2.446 lipophilicity

TPSA:

436.83 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

3 (1 aromatic)

Chiral Centers:

Fsp³:

0.6471 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006858

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

Back to Compounds