SCS-C007894

berninamycin A

Pathway: Amino acids and Peptides Superclass: Oligopeptides Class: Cyclic peptides | RiPPs-Thiopeptides

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

Streptomyces sp. SCSIO 11878 (bacterium)

Kingdom Bacillati Phylum Actinomycetota Class Actinomycetes Order Kitasatosporales Family Streptomycetaceae Genus Streptomyces Species NA

South China Sea · 1396 m · E 118°58.2475′, N 22°2.3689′

DOI: 10.1039/d1ob01759d · Organic & Biomolecular Chemistry

Drug-likeness (Lipinski Ro5)

Molecular Weight

1146.1 Da

Threshold ≤ 500

ALogP

0.10

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:

C51H51N15O15S

Molecular Weight:

1146.1260 Da

SMILES:

C=C(NC(=O)C(=C)NC(=O)c1ccc2c(n1)-c1coc(n1)C(=C)NC(=O)C(=C)NC(=O)c1nc(oc1C)C(=C)NC(=O)[C@H](C(C)(C)O)NC(=O)C(=C)NC(=O)c1nc(oc1C)/C(=C/C)NC(=O)[C@H]([C@@H](C)O)NC(=O)c1csc-2n1)C(N)=O

InChIKey:

                        CAFFHXXVDGAVPH-DKFXDEMXSA-N
                        
                    

InChI:

InChI=1S/C51H51N15O15S/c1-13-28-49-65-34(26(10)81-49)45(76)56-21(5)40(71)66-36(51(11,12)78)46(77)58-23(7)48-64-33(25(9)80-48)44(75)55-20(4)39(70)57-22(6)47-61-30(16-79-47)35-27(50-62-31(17-82-50)42(73)63-32(24(8)67)43(74)60-28)14-15-29(59-35)41(72)54-19(3)38(69)53-18(2)37(52)68/h13-17,24,32,36,67,78H,2-7H2,1,8-12H3,(H2,52,68)(H,53,69)(H,54,72)(H,55,75)(H,56,76)(H,57,70)(H,58,77)(H,60,74)(H,63,73)(H,66,71)/b28-13-/t24-,32+,36-/m1/s1

Calculated Properties

ALogP:

0.098 lipophilicity

TPSA:

449.32 Å² polar surface area

H-Bond Donors:

H-Bond Acceptors:

Rotatable Bonds:

Ring Count:

6 (5 aromatic)

Chiral Centers:

Fsp³:

0.1961 fraction sp³ carbon

Database Information

Compound ID:

SCS-C007894

NPClassifier Pathway:

Amino acids and Peptides

NPClassifier Superclass:

Oligopeptides

NPClassifier Class:

Cyclic peptides RiPPs-Thiopeptides

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	MIC	Gram-positive bacteria	0.2–4.0 μg mL?1	10.1039/d1ob01759d Organic & Biomolecular Chemistry
Antibacterial	MIC	Gram-negative bacteria	> 64.0 μg mL?1	10.1039/d1ob01759d Organic & Biomolecular Chemistry

Back to Compounds