Cinnabaramide A
AlkaPlorer ID: AK011241
Synonym: None
IUPAC Name: (1R,4R,5S)-1-[(S)-[(1S)-cyclohex-2-en-1-yl]-hydroxymethyl]-4-hexyl-5-methyl-6-oxa-2-azabicyclo[3.2.0]heptane-3,7-dione
Structure
SMILES: CCCCCC[C@H]1C(=O)N[C@@]2([C@@H](O)[C@@H]3C=CCCC3)C(=O)O[C@@]12C
InChI: InChI=1S/C19H29NO4/c1-3-4-5-9-12-14-16(22)20-19(17(23)24-18(14,19)2)15(21)13-10-7-6-8-11-13/h7,10,13-15,21H,3-6,8-9,11-12H2,1-2H3,(H,20,22)/t13-,14+,15+,18+,19+/m1/s1
InChIKey: KAZLTNBVAYOUNF-MUAMBBPCSA-N
Reference
Cinnabaramides A−G: Analogues of Lactacystin and Salinosporamide from a Terrestrial Streptomycete
PubChem CID: 9862556
LOTUS: LTS0110141
SuperNatural Ⅲ: SN0180684-03
NPASS: NPC14537
{NPAtlas: NPA011227
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Streptomyces sp. | Streptomyces | Streptomycetaceae | Kitasatosporales | Actinomycetes | Actinomycetota | None | Bacteria |
Properties Information
Molecule Weight: 335.44400000000013
TPSA？: 75.63000000000001
MolLogP？: 2.4743000000000004
Number of H-Donors: 2
Number of H-Acceptors: 4
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Homo sapiens | 20S proteasome | IC50 | 1.0 | nM | 10.1021/np060162u |
| Homo sapiens | HCT-116 | Activity | 10.0 | nM | 10.1021/np060162u |
| Homo sapiens | MDA-MB-231 | IC50 | 1000.0 | nM | 10.1021/np060162u |
| Homo sapiens | NCI-H460 | IC50 | 1000.0 | nM | 10.1021/np060162u |
| Homo sapiens | PBMC | IC50 | 500.0 | nM | 10.1021/np060162u |
| Homo sapiens | Trypsin | Activity | nan | None | 10.1021/np060162u |
| None | No relevant target | Stability | 50.0 | % | 10.1021/np060162u |
| None | Unchecked | Activity | nan | None | 10.1021/np060162u |