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Senecionine
- Family: Leguminosae/Fabaceae, Asteraceae-Compositae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C\1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 |
|---|---|
| InChI | InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-/t11-,14-,15-,18-/m1/s1 |
| InChIKey | HKODIGSRFALUTA-JTLQZVBZSA-N |
| Formula | C18H25NO5 |
| HBA | 6 |
| HBD | 1 |
| MW | 335.4 |
| Rotatable Bonds | 0 |
| TPSA | 76.07 |
| LogP | 1.19 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.67 |
| Exact Mass | 335.17 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Senecio abrotanifolius | Asteraceae-Compositae | Plantae | 189225 |
| 2 | Senecio boissieri | Asteraceae-Compositae | Plantae | 214893 |
| 3 | Senecio carniolicus | Asteraceae-Compositae | Plantae | 189240 |
| 4 | Senecio halleri | Asteraceae-Compositae | Plantae | 214899 |
| 5 | Senecio incanus | Asteraceae-Compositae | Plantae | 189239 |
| 6 | Senecio leucophyllus | Asteraceae-Compositae | Plantae | 214900 |
| 7 | Senecio minutus | Asteraceae-Compositae | Plantae | 189241 |
| 8 | Senecio persoonii | Asteraceae-Compositae | Plantae | 214902 |
| 9 | Senecio cannabifolius | Asteraceae-Compositae | Plantae | 189232 |
| 10 | Senecio delphinifolius | Asteraceae-Compositae | Plantae | 214896 |
| 11 | Senecio othonnae | Asteraceae-Compositae | Plantae | 214901 |
| 12 | Senecio paludosus | Asteraceae-Compositae | Plantae | 189244 |
| 13 | Senecio alpinus | Asteraceae-Compositae | Plantae | 189227 |
| 14 | Senecio ambiguus | Asteraceae-Compositae | Plantae | 189228 |
| 15 | Senecio aquaticus | Asteraceae-Compositae | Plantae | 189230 |
| 16 | Senecio chrysanthemoides | Asteraceae-Compositae | Plantae | 189235 |
| 17 | Senecio cineraria | Asteraceae-Compositae | Plantae | 252537 |
| 18 | Senecio giganteus | Asteraceae-Compositae | Plantae | 214897 |
| 19 | Senecio gnaphalodes | Asteraceae-Compositae | Plantae | 2868836 |
| 20 | Senecio jacobaea | Asteraceae-Compositae | Plantae | 98722 |
| 21 | Senecio pancicii | Asteraceae-Compositae | Plantae | 189245 |
| 22 | Senecio subalpinus | Asteraceae-Compositae | Plantae | 189250 |
| 23 | Solanecio angulatus | Asteraceae-Compositae | Plantae | 1670880 |
| 24 | Solanecio mannii | Asteraceae-Compositae | Plantae | — |
| 25 | Solanecio tuberosus var. tuberosus | Asteraceae-Compositae | Plantae | 189251 |
| 26 | Crotalaria agatiflora | Leguminosae/Fabaceae | Plantae | 1127378 |
| 27 | Crotalaria axillaris | Leguminosae/Fabaceae | Plantae | 1132589 |
| 28 | Crotalaria emarginella | Leguminosae/Fabaceae | Plantae | 1132599 |
| 29 | Crotalaria gillettii | Leguminosae/Fabaceae | Plantae | 1132206 |
| 30 | Crotalaria phillipsiae | Leguminosae/Fabaceae | Plantae | 3086461 |
Showing of synonyms
Senecionine
Aureine
Senecionin
12-Hydroxysenecionan-11,16-dione
CCRIS 4340
CHEBI:9107
HSDB 3535
UNII-BO6N1U5YG6
BO6N1U5YG6
NSC 89935
BRN 0934445
Senecionan-11,16-dione, 12-hydroxy-
AI3-51771
NSC-89935
DTXSID40871615
DTXCID501474669
130-01-8
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-
NSC89935
(1,6)Dioxacyclododecino(2,3,4-gh)pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-, (3Z,5R,6R,14aR,14bR)-
C18H25NO5
(1R,4Z,6R,7R,17R)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
MFCD00221720
Aureine\, Senecionin
Senecionine (Standard)
SENECIONINE [MI]
(-)-SENECIONINE
SCHEMBL896098
Senecionan-11, 12-hydroxy-
CHEMBL362153
Senecionine, analytical standard
HY-N2560R
HKODIGSRFALUTA-JTLQZVBZSA-N
Senecionine, >=95.0% (GC)
HY-N2560
MSK40300
BDBM50480301
AKOS037514834
CCG-208634
NCGC00163621-01
(Z)-ethylidene-hydroxy-dimethyl-[?]dione
1ST40300
AC-34604
AS-79841
DA-67538
FS161593
CS-0022892
Senecionine 100 microg/mL in Methanol:Water
C06176
Q2083871
WLN: T55-12-1A Q EN IOVY OVO BUTJ KU2 M NQ N
WLN: T55-12- 1A Q EN IOVY OVO BUTJ KU2 M1 NQ N1
(5R,6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-5,6-dimethyl-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
[1,6]Dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione,3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl-,(3Z,5R,6R,14aR,14bR)-
- Pelser PB, De Vos H, et al. (2005). Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae). Phytochemistry,2005,66,1285-1295. [View] [PubMed]
- Asres K, Sporer F, et al. (2008). Occurrence of pyrrolizidine alkaloids in three Ethiopian Solanecio species. Biochemical Systematics and Ecology,2008,36(5-6),399-407. [View] [PubMed]
- Asres K, Sporer F, et al. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
Pubchem:
5280906
Cas:
130-01-8
Gnps:
CCMSLIB00005770134
Zinc:
ZINC000095851257
Kegg Ligand:
C06176
Chebi:
9107
Nmrshiftdb2:
60026150
Metabolights:
MTBLC9107
Chembl:
CHEMBL362153
Bindingdb:
50480301
CPRiL:
6189
SMILES: C1OC(=O)CCCC(=C)C(=O)OC(C2C1=3)CCN2CC3
Level: 0
Mol. Weight: 277.32 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.88
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.93
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -3.02
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.61
- Plasma Protein Binding
- 28.47
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.39
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.74
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.09
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 9.81
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Toxic
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -5.1
- Rat (Acute)
- 3.72
- Rat (Chronic Oral)
- 1.76
- Fathead Minnow
- 3.94
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 377.38
- Hydration Free Energy
- -9.95
- Log(D) at pH=7.4
- 1.2
- Log(P)
- 1.29
- Log S
- -2.19
- Log(Vapor Pressure)
- -7.28
- Melting Point
- 172.63
- pKa Acid
- 6.84
- pKa Basic
- 6.71
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7876 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7876 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7116 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7116 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7086 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7086 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7057 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.7057 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7035 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7035 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7033 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7033 |