Retrorsine
AlkaPlorer ID: AK001429
Synonym: None
IUPAC Name: (1R,4E,6R,7S,17R)-4-ethylidene-7-hydroxy-7-(hydroxymethyl)-6-methyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
Structure
SMILES: C/C=C1\C[C@@H](C)[C@](O)(CO)C(=O)OCC2=CCN3CC[C@@H](OC1=O)[C@@H]23
InChI: InChI=1S/C18H25NO6/c1-3-12-8-11(2)18(23,10-20)17(22)24-9-13-4-6-19-7-5-14(15(13)19)25-16(12)21/h3-4,11,14-15,20,23H,5-10H2,1-2H3/b12-3+/t11-,14-,15-,18-/m1/s1
InChIKey: BCJMNZRQJAVDLD-FXGRWVCYSA-N
Reference
Usaramine, a new pyrrolizidine alkaloid from Crotalaria usaarmoensis E. G. Baker
PubChem CID: 5281756
CAS: 15503-87-4
LOTUS: LTS0173272
SuperNatural Ⅲ: SN0021754-07
NPASS: NPC201889
Source
| Species | Genus | Family | Order | Class | Phylum | Kingdom | Domain |
|---|---|---|---|---|---|---|---|
| Senecio scandens | Senecio | Asteraceae | Asterales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
| None | Senecio | Asteraceae | Asterales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
| None | Senecio | Asteraceae | Asterales | Magnoliopsida | Streptophyta | Viridiplantae | Eukaryota |
Properties Information
Molecule Weight: 351.3990000000001
TPSA？: 96.3
MolLogP？: 0.1652
Number of H-Donors: 2
Number of H-Acceptors: 7
RingCount: 3
Activities Information
| Organism | Target Name | Standard Type | Standard Value | Standard Units | doi |
|---|---|---|---|---|---|
| Cricetulus griseus | CHO | EC50 | 100.0 | ug.mL-1 | 10.1016/jbse.2007.08.015 |
| Electrophorus electricus | Acetylcholinesterase | Inhibition | 4.15 | % | 10.1016/j.bmc.2012.09.040 |
| Equus caballus | Cholinesterase | Inhibition | -3.05 | % | 10.1016/j.bmc.2012.09.040 |
| Homo sapiens | A204 | IC50 | 120.0 | ug.mL-1 | 10.1021/np50058a005 |
| Human immunodeficiency virus 1 | Human immunodeficiency virus type 1 reverse transcriptase | IC50 | 200.0 | ug.mL-1 | 10.1021/np50073a012 |
| Lactuca sativa | Lactuca sativa | Inhibition | 50.0 | % | 10.1016/jbse.2007.08.015 |
| Lactuca sativa | Lactuca sativa | Inhibition | nan | % | 10.1016/jbse.2007.08.015 |
| Leptinotarsa decemlineata | Leptinotarsa decemlineata | EC50 | 50.0 | microg/cm2 | 10.1016/jbse.2007.08.015 |
| Leptinotarsa decemlineata | Leptinotarsa decemlineata | EC50 | nan | None | 10.1016/jbse.2007.08.015 |
| Myzus persicae | Myzus persicae | Activity | 30.0 | % | 10.1016/jbse.2007.08.015 |
| Myzus persicae | Myzus persicae | Activity | 44.0 | % | 10.1016/jbse.2007.08.015 |
| Rhopalosiphum padi | Rhopalosiphum padi | Activity | 40.0 | % | 10.1016/jbse.2007.08.015 |
| Rhopalosiphum padi | Rhopalosiphum padi | Activity | 46.0 | % | 10.1016/jbse.2007.08.015 |
| Spodoptera littoralis | Spodoptera littoralis | Activity | 88.0 | % | 10.1016/jbse.2007.08.015 |
| Spodoptera littoralis | Spodoptera littoralis | Activity | 90.0 | % | 10.1016/jbse.2007.08.015 |
| Spodoptera littoralis | Spodoptera littoralis | Activity | 92.0 | % | 10.1016/jbse.2007.08.015 |
| Spodoptera littoralis | Spodoptera littoralis | Activity | 102.0 | % | 10.1016/jbse.2007.08.015 |
| Spodoptera littoralis | Spodoptera littoralis | EC50 | 50.0 | microg/cm2 | 10.1016/jbse.2007.08.015 |
| Spodoptera littoralis | Spodoptera littoralis | EC50 | nan | None | 10.1016/jbse.2007.08.015 |
| None | ADMET | EC50 | 100.0 | ug.mL-1 | 10.1016/jbse.2007.08.015 |