Jacobine
PubChem CID: 442741
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| Compound Synonyms | JACOBINE, 6870-67-3, Jacobine., CCRIS 5777, HSDB 3500, NSC 89936, BRN 0054580, GM32U80H1R, JACOBINE [IARC], UNII-GM32U80H1R, DTXSID501020078, 4-27-00-06827 (Beilstein Handbook Reference), NSC-89936, JACOBINE (IARC), 15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione, (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxysenecionan-11,16-dione, 12beta-Hydroxy-12alpha,13beta-dimethylsenec-1-enine-15S-spiro-2'-(3'R-methyloxiran), Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)-, Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15alpha,20R)-, 471-14-7, SENECIONAN-11,16-DIONE, 15,20-EPOXY-15,20-DIHYDRO-12-HYDROXY-, (15.ALPHA.,20S)-, (1R,3'S,4S,6R,7R,17R)-7-hydroxy-3',6,7-trimethylspiro[2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-4,2'-oxirane]-3,8-dione, (2S,3S,5'R,6'R,9a1'R,14a'R)-6'-hydroxy-3,5',6'-trimethyl-5',6',9',9a1',11',13',14',14a'-octahydro-2'H-spiro[oxirane-2,3'-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine]-2',7'(4'H)-dione, [(1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl] (2R)-2-hydroxy-2-[(1R)-1-hydroxyethyl]-3-methyl-butanoate, SPIRO((1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-3(2H),2'-OXIRANE)-2,7(4H)-DIONE, 5,6,9,11,13,14,14A,14B-OCTAHYDRO-6-HYDROXY-3',5,6-TRIMETHYL-, (2'S,3'S,5R,6R,14AR,14BR)-, ((1R,8R)-7-(hydroxymethyl)-2,3,5,8-tetrahydro-1H-pyrrolizin-1-yl) (2R)-2-hydroxy-2-((1R)-1-hydroxyethyl)-3-methyl-butanoate, (1R,3'S,4S,6R,7R,17R)-7-hydroxy-3',6,7-trimethylspiro(2,9-dioxa-14-azatricyclo(9.5.1.014,17)heptadec-11-ene-4,2'-oxirane)-3,8-dione, CHEBI:6080, Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-.alpha.,20S)-, DTXCID201477919, AKOS027326873, 1ST14167, BJ161539, DA-64608, HY-124058, CS-0084068, NS00066968, Q27107031, 15,20Epoxy15,20dihydro12hydroxysenecionan11,16dione, (15alpha,20R)15,20Epoxy15,20dihydro12hydroxysenecionan11,16dione, 12betaHydroxy12alpha,13betadimethylsenec1enine15Sspiro2'(3'Rmethyloxiran), Senecionan11,16dione, 15,20epoxy15,20dihydro12hydroxy, (15alpha,20R), (15 alpha,20R)15,20-epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione, (15alpha,20R)15,20-Epoxy-15,20-dihydro-12-hydroxy-senecionan-11,16-dione, Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydroxy-, (15-alpha,20S)-(9CI), SENECIONAN-11,16-DIONE, 15,20-EPOXY-15,20-DIHYDRO-12-HYDROXY-, (15ALPHA,20S)-, 12BETA-HYDROXY-12ALPHA,13BETA-DIMETHYLSENEC-1-ENINE-15S-SPIRO-2'-(3'R-METHYL OXIRAN), Jacobine, Spiro[[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-3(2H),2'-oxirane]-2,7(4H)-dione, 5,6,9,11,13,14,14a,14b-octahydro-6-hydroxy-3',5,6-trimethyl-, (2'S,3'S,5R,6R,14aR,14bR)-, Jacobine (6CI,7CI,8CI), Senecionan-11,16-dione, 15,20-epoxy-15,20-dihydro-12-hydr |
|---|---|
| Ghose Rule | True |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 88.6 |
| Hydrogen Bond Donor Count | 1.0 |
| Pfizer 3 75 Rule | True |
| Scaffold Graph Level | CC1CCCC2(CC2)C(C)CC2CCC3CCC(CC1)C32 |
| Np Classifier Class | Pyrrolizidine alkaloids |
| Deep Smiles | O=COCC=CCN[C@H]5[C@@H]CC5))OC=O)[C@@]C[C@H][C@@]%15C)O))C)))O[C@H]3C |
| Heavy Atom Count | 25.0 |
| Scaffold Graph Node Level | OC1CCCC2(CO2)C(O)OC2CCN3CCC(CO1)C23 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 647.0 |
| Database Name | imppat_phytochem;pubchem |
| Defined Atom Stereocenter Count | 6.0 |
| Iupac Name | (1R,3'S,4S,6R,7R,17R)-7-hydroxy-3',6,7-trimethylspiro[2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-4,2'-oxirane]-3,8-dione |
| Veber Rule | True |
| Classyfire Superclass | Alkaloids and derivatives |
| Xlogp | 0.3 |
| Gsk 4 400 Rule | True |
| Molecular Formula | C18H25NO6 |
| Scaffold Graph Node Bond Level | O=C1CCCC2(CO2)C(=O)OC2CCN3CC=C(CO1)C23 |
| Inchi Key | IAPHXJRHXBQDQJ-WKMWQDDRSA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 0.0 |
| Synonyms | jacobine |
| Esol Class | Soluble |
| Functional Groups | CC=C(C)C, CN(C)C, CO, COC(C)=O, C[C@@H]1O[C@]1(C)C(=O)OC |
| Compound Name | Jacobine |
| Exact Mass | 351.168 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 351.168 |
| Hydrogen Bond Acceptor Count | 7.0 |
| Molecular Weight | 351.4 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 6.0 |
| Total Bond Stereocenter Count | 0.0 |
| Lipinski Rule Of 5 | True |
| Inchi | InChI=1S/C18H25NO6/c1-10-8-18(11(2)25-18)16(21)24-13-5-7-19-6-4-12(14(13)19)9-23-15(20)17(10,3)22/h4,10-11,13-14,22H,5-9H2,1-3H3/t10-,11+,13-,14-,17-,18+/m1/s1 |
| Smiles | C[C@@H]1C[C@]2([C@@H](O2)C)C(=O)O[C@@H]3CCN4[C@@H]3C(=CC4)COC(=O)[C@]1(C)O |
| Np Classifier Biosynthetic Pathway | Alkaloids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Np Classifier Superclass | Ornithine alkaloids |
- 1. Outgoing r'ship
FOUND_INto/from Crassocephalum Crepidioides (Plant) Rel Props:Reference:ISBN:9788185042138 - 2. Outgoing r'ship
FOUND_INto/from Senecio Chrysanthemoides (Plant) Rel Props:Reference:ISBN:9788185042053 - 3. Outgoing r'ship
FOUND_INto/from Senecio Jacobaea (Plant) Rel Props:Reference:ISBN:9788172361266