intermedine
AlkaPlorer ID: AK002980
Synonym: '', 'MLS002694968', 'beta-MSH', 'Morifoline', 'Heliotridine trachelanthate', 'indicine', '9-(+)-Trachelanthylretronecine', 'Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, 1S-1.alpha.,7(2R*,3R*),7a.alpha.-', 'O-Demethylheliotrine', 'Lycopsamine', 'Echinatine', 'Intermedine', 'Butanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, (2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl)methyl ester, 1S-(1.alpha.,7(2R,3S),7a.alpha.)-', '9-Viridiflorylretronecine', '(+)-Echinatine', 'MLSMR', 'Retronecine 9-(-)-viridiflorate', '9-(+)-Trachelanthylheliotridine', 'Indicine', '(1R,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-ylmethyl (2R,3S)-2,3-dihydroxy-2-isopropylbutanoate', 'ECHINATINE', 'Rinderine', 'SMR001560881'
IUPAC Name: [(7R,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2R)-2-hydroxy-2-[(1S)-1-hydroxyethyl]-3-methylbutanoate
Structure
SMILES: CC(C)[C@](O)(C(=O)OCC1=CCN2CC[C@@H](O)[C@@H]12)[C@H](C)O
InChI: InChI=1S/C15H25NO5/c1-9(2)15(20,10(3)17)14(19)21-8-11-4-6-16-7-5-12(18)13(11)16/h4,9-10,12-13,17-18,20H,5-8H2,1-3H3/t10-,12+,13+,15+/m0/s1
InChIKey: SFVVQRJOGUKCEG-XTWPYSKKSA-N
Reference
Pyrrolizidine alkaloids from Messerschmidia argentea
PubChem CID: 73614
CAS: 480-82-0
LOTUS: LTS0077208
NPASS: NPC80439
data_source: manually
Source
Properties Information
Molecule Weight: 299.367
TPSA？: 90.23
MolLogP？: -0.3273000000000007
Number of H-Donors: 3
Number of H-Acceptors: 6
RingCount: 2
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Homo sapiens | A498 | GI50 | 374973.0 | nM | None |
| Homo sapiens | A549 | GI50 | 374973.0 | nM | None |
| Homo sapiens | CAKI-1 | GI50 | 374973.0 | nM | None |
| Homo sapiens | CCRF-CEM | GI50 | 374973.0 | nM | None |
| Homo sapiens | COLO 205 | GI50 | 374973.0 | nM | None |
| Homo sapiens | DLD-1 | GI50 | 374973.0 | nM | None |
| Homo sapiens | DMS-114 | GI50 | 368128.97 | nM | None |
| Homo sapiens | DMS-273 | GI50 | 374973.0 | nM | None |
| Homo sapiens | EKVX | GI50 | 374973.0 | nM | None |
| Homo sapiens | HCC 2998 | GI50 | 374973.0 | nM | None |
| Homo sapiens | HCT-116 | GI50 | 374973.0 | nM | None |
| Homo sapiens | HCT-15 | GI50 | 374973.0 | nM | None |
| Homo sapiens | HL-60 | GI50 | 374973.0 | nM | None |
| Homo sapiens | HOP-18 | GI50 | 374973.0 | nM | None |
| Homo sapiens | HOP-62 | GI50 | 334965.44 | nM | None |
| Homo sapiens | HOP-92 | GI50 | 374973.0 | nM | None |
| Homo sapiens | HT-29 | GI50 | 374973.0 | nM | None |
| Homo sapiens | IGROV-1 | GI50 | 308318.8 | nM | None |
| Homo sapiens | K562 | GI50 | 374973.0 | nM | None |
| Homo sapiens | KM12 | GI50 | 374973.0 | nM | None |
| Homo sapiens | KM-20L2 | GI50 | 374973.0 | nM | None |
| Homo sapiens | LOX IMVI | GI50 | 174180.69 | nM | None |
| Homo sapiens | M19-MEL | GI50 | 255270.13 | nM | None |
| Homo sapiens | Malme-3M | GI50 | 374973.0 | nM | None |
| Homo sapiens | MCF7 | GI50 | 374973.0 | nM | None |
| Homo sapiens | MOLT-4 | GI50 | 374973.0 | nM | None |
| Homo sapiens | NCI/ADR-RES | GI50 | 374973.0 | nM | None |
| Homo sapiens | NCI-H226 | GI50 | 374973.0 | nM | None |
| Homo sapiens | NCI-H23 | GI50 | 374973.0 | nM | None |
| Homo sapiens | NCI-H322M | GI50 | 374973.0 | nM | None |
| Homo sapiens | NCI-H460 | GI50 | 367282.3 | nM | None |
| Homo sapiens | NCI-H522 | GI50 | 59429.22 | nM | None |
| Homo sapiens | OVCAR-3 | GI50 | 374973.0 | nM | None |
| Homo sapiens | OVCAR-4 | GI50 | 374973.0 | nM | None |
| Homo sapiens | OVCAR-5 | GI50 | 277971.33 | nM | None |
| Homo sapiens | OVCAR-8 | GI50 | 374973.0 | nM | None |
| Homo sapiens | RPMI-8226 | GI50 | 374973.0 | nM | None |
| Homo sapiens | RXF 393 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SF-268 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SF-295 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SF-539 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SK-MEL-2 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SK-MEL-28 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SK-MEL-5 | GI50 | 80723.5 | nM | None |
| Homo sapiens | SK-OV-3 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SN12C | GI50 | 374973.0 | nM | None |
| Homo sapiens | SN12K1 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SNB-19 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SNB-75 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SNB-78 | GI50 | 374973.0 | nM | None |
| Homo sapiens | SW-620 | GI50 | 236591.97 | nM | None |
| Homo sapiens | U-251 | GI50 | 374973.0 | nM | None |
| Homo sapiens | UACC-257 | GI50 | 374973.0 | nM | None |
| Homo sapiens | UACC-62 | GI50 | 374973.0 | nM | None |
| Homo sapiens | UO-31 | GI50 | 374973.0 | nM | None |
| Homo sapiens | XF498 | GI50 | 374973.0 | nM | None |
| Mus musculus | P388 | GI50 | 374973.0 | nM | None |
| Mus musculus | P388/ADR | GI50 | 374973.0 | nM | None |
| None | Unchecked | IC50 | 490.0 | nM | 10.1016/j.ejmech.2021.114035 |
| None | Unchecked | IC50 | 12500.0 | nM | 10.1016/j.ejmech.2021.114035 |