SCS-C006111

mathermycin

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: RiPPs-Amatoxins and Phallotoxins | RiPPs-Lanthipeptides

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Chemical Structure

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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

Marinactinospora thermotolerans (NA)

Original source name: Marinactinospora thermotolerans | Streptomyces lividans | Escherichia coli

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Streptosporangiales Family Nocardiopsidaceae Genus Marinactinospora Species Marinactinospora thermotolerans

South China Sea · 3865 m

DOI: 10.1128/aem.00926-17 · Applied and Environmental Microbiology

Drug-likeness (Lipinski Ro5)

Molecular Weight

1854.1 Da

Threshold ≤ 500

ALogP

-9.54

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:

C80H116N20O25S3

Molecular Weight:

1854.1240 Da

SMILES:

CC[C@H](C)[C@@H]1NC(=O)[C@H]2NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H]3CCCN3C(=O)CNC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H]3CNCCCC[C@@H](C(=O)O)NC(=O)C4NC(=O)[C@H]([C@H](C)O)NC(=O)CNC(=O)[C@H]([C@@H](O)C(=O)O)NC(=O)[C@@H](CS[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](C)NC(=O)[C@@H](N)CS[C@@H]4C)C(=O)N[C@@H](CSC2C)C(=O)N3)NC(=O)[C@H](C)NC1=O

InChIKey:

                        DNVMJLMJKLCCOS-KSFQLRDRSA-N
                        
                    

InChI:

InChI=1S/C80H116N20O25S3/c1-9-36(2)56-74(117)86-38(4)64(107)92-52-35-128-41(7)58-77(120)93-51-34-127-42(8)60(78(121)95-56)96-67(110)48(28-44-21-14-11-15-22-44)89-72(115)53-24-18-26-100(53)55(104)31-84-66(109)47(27-43-19-12-10-13-20-43)88-68(111)49(90-70(51)113)29-82-25-17-16-23-46(79(122)123)87-76(119)59(40(6)126-33-45(81)65(108)85-37(3)63(106)91-50(32-101)69(112)97-58)98-75(118)57(39(5)102)94-54(103)30-83-73(116)61(99-71(52)114)62(105)80(124)125/h10-15,19-22,36-42,45-53,56-62,82,101-102,105H,9,16-18,23-35,81H2,1-8H3,(H,83,116)(H,84,109)(H,85,108)(H,86,117)(H,87,119)(H,88,111)(H,89,115)(H,90,113)(H,91,106)(H,92,107)(H,93,120)(H,94,103)(H,95,121)(H,96,110)(H,97,112)(H,98,118)(H,99,114)(H,122,123)(H,124,125)/t36-,37-,38-,39-,40+,41+,42?,45-,46-,47-,48-,49-,50-,51-,52+,53-,56-,57-,58-,59?,60-,61-,62+/m0/s1

Calculated Properties

ALogP:

-9.537 lipophilicity

TPSA:

688.35 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

7 (2 aromatic)

Chiral Centers:

Fsp³:

0.6000 fraction sp³ carbon

Database Information

Compound ID:

SCS-C006111

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

RiPPs-Amatoxins and Phallotoxins RiPPs-Lanthipeptides

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
Antibacterial	growth inhibition	Bacillus subtilis LH45	mathermycin exhibited antimicrobial potency similar to that of cinnamycin against B. subtilis LH45	10.1128/aem.00926-17 Applied and Environmental Microbiology

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