SCS-C008001
atratumycin
Pathway: Amino acids and Peptides | Polyketides
Superclass: Oligopeptides
Class: Cyclic peptides | Depsipeptides
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.
Source Information
Streptomyces atratus
(NA)
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces atratus
South China Sea
DOI:
10.1021/acs.orglett.9b00208
· Organic Letters
Drug-likeness (Lipinski Ro5)
Molecular Weight
1325.5 Da
Threshold ≤ 500
ALogP
-0.09
Threshold ≤ 5
H-Bond Donors
14
Threshold ≤ 5
H-Bond Acceptors
16
Threshold ≤ 10
3 violations (MW, HBD, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C68H84N12O16
Molecular Weight:
1325.4880 Da
SMILES:
Cc1ccccc1/C=C/C(=O)N[C@@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc2c[nH]c3ccccc23)C(=O)N[C@H](CC(N)=O)C(=O)N[C@@H]([C@@H](O)c2ccccc2)C(=O)N2CCC[C@H]2C(=O)N[C@H](C(C)C)C(=O)NCC(=O)N[C@H](CC(C)C)C(=O)N[C@H](Cc2ccc(O)cc2)C(=O)O[C@@H]1C
InChIKey:
UFPVKIKINBECRQ-CNSCIBEJSA-N
InChI:
InChI=1S/C68H84N12O16/c1-36(2)29-47-60(87)75-50(30-40-22-25-44(82)26-23-40)68(95)96-39(6)57(77-54(84)27-24-41-16-11-10-15-38(41)5)66(93)76-51(35-81)63(90)73-48(31-43-33-70-46-20-13-12-19-45(43)46)61(88)74-49(32-53(69)83)62(89)79-58(59(86)42-17-8-7-9-18-42)67(94)80-28-14-21-52(80)64(91)78-56(37(3)4)65(92)71-34-55(85)72-47/h7-13,15-20,22-27,33,36-37,39,47-52,56-59,70,81-82,86H,14,21,28-32,34-35H2,1-6H3,(H2,69,83)(H,71,92)(H,72,85)(H,73,90)(H,74,88)(H,75,87)(H,76,93)(H,77,84)(H,78,91)(H,79,89)/b27-24+/t39-,47-,48+,49-,50-,51+,52+,56-,57+,58+,59+/m1/s1
Calculated Properties
ALogP:
-0.085 lipophilicity
TPSA:
428.08 Ų polar surface area
H-Bond Donors:
14
H-Bond Acceptors:
16
Rotatable Bonds:
15
Ring Count:
7
(5 aromatic)
Chiral Centers:
11
Fsp³:
0.4118 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008001
NPClassifier Pathway:
Amino acids and Peptides
Polyketides
NPClassifier Superclass:
Oligopeptides
NPClassifier Class:
Cyclic peptides
Depsipeptides
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
Natural product databases
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 |
|---|---|---|---|---|
| Antimycobacterial | MIC | Mycobacterium tuberculosis H37Ra | 3.8 μM | 10.1021/acs.orglett.9b00208 Organic Letters |
| Antimycobacterial | MIC | Mycobacterium tuberculosis H37Rv | 14.6 μM | 10.1021/acs.orglett.9b00208 Organic Letters |
| Antitumor | — | panel of six cancerous and two normal/healthy human cell lines | — Structured numeric value is not available in this record; see the primary reference. | 10.1021/acs.orglett.9b00208 Organic Letters |