SCS-C008002
Grincamycin F
Pathway: Polyketides
Superclass: Polycyclic aromatic polyketides
Class: Angucyclines
Glycoside
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.
Source Information
Streptomyces lusitanus SCSIO LR32
(NA)
Original source name: Streptomyces Lusitanus SCSIO LR32
Kingdom
Bacillati
Phylum
Actinomycetota
Class
Actinomycetes
Order
Kitasatosporales
Family
Streptomycetaceae
Genus
Streptomyces
Species
Streptomyces lusitanus
South China Sea
DOI:
10.1021/acschemneuro.0c00206
· ACS Chemical Neuroscience
Drug-likeness (Lipinski Ro5)
Molecular Weight
1071.1 Da
Threshold ≤ 500
ALogP
5.60
Threshold ≤ 5
H-Bond Donors
5
Threshold ≤ 5
H-Bond Acceptors
20
Threshold ≤ 10
3 violations (MW, ALogP, HBA) — not drug-like by Ro5
Chemical Properties
Molecular Formula:
C57H66O20
Molecular Weight:
1071.1350 Da
SMILES:
C[C@@H]1O[C@@H](O[C@H]2CC[C@H](O[C@@H]3C[C@H](c4cc5c(-c6ccc(O)cc6)c(=O)oc6c5c(c4O)C(=O)C4=C6[C@@]5(O)C(=O)C[C@](C)(O[C@H]6CC[C@H](O[C@H]7CCC(=O)[C@H](C)O7)[C@H](C)O6)C[C@@]5(O)C=C4)O[C@H](C)[C@H]3O)O[C@H]2C)CCC1=O
InChIKey:
JUXOROUAHRHMJD-KPBLJPKWSA-N
InChI:
InChI=1S/C57H66O20/c1-25-35(59)11-15-42(69-25)73-37-13-17-44(71-27(37)3)75-40-22-39(68-29(5)50(40)62)33-21-34-46(30-7-9-31(58)10-8-30)54(65)76-53-47(34)48(52(33)64)51(63)32-19-20-56(66)24-55(6,23-41(61)57(56,67)49(32)53)77-45-18-14-38(28(4)72-45)74-43-16-12-36(60)26(2)70-43/h7-10,19-21,25-29,37-40,42-45,50,58,62,64,66-67H,11-18,22-24H2,1-6H3/t25-,26-,27-,28-,29+,37-,38-,39+,40+,42-,43-,44-,45-,50+,55-,56-,57-/m0/s1
Calculated Properties
ALogP:
5.596 lipophilicity
TPSA:
282.71 Ų polar surface area
H-Bond Donors:
5
H-Bond Acceptors:
20
Rotatable Bonds:
10
Ring Count:
11
(3 aromatic)
Chiral Centers:
17
Fsp³:
0.5965 fraction sp³ carbon
Database Information
Compound ID:
SCS-C008002
NPClassifier Pathway:
Polyketides
NPClassifier Superclass:
Polycyclic aromatic polyketides
NPClassifier Class:
Angucyclines
Glycoside:
Yes
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 |
|---|---|---|---|---|
| Antitumor | — | mouse melanoma | Grincamycin (GCN) B?F are newly isolated from marine-derived Streptomyces Lusitanus SCSIO LR32 and show strongly inhibitory effect on various cancer cell lines such as HepG2 (hepatic carcinoma), SW-1990 (pancreatic cancer), Hela (cervical cancer), NCI-H460 (lung cancer), MCF-7 (breast cancer), and B12 (mouse melanoma). [...] the results showed that GCN B held the strongest inhibitory effects among the five compounds | 10.1021/acschemneuro.0c00206 ACS Chemical Neuroscience |