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Seneciphylline
- Family: Asteraceae-Compositae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C\1/CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3 |
|---|---|
| InChI | InChI=1S/C18H23NO5/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/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15-,18-/m1/s1 |
| InChIKey | FCEVNJIUIMLVML-QPSVUOIXSA-N |
| Formula | C18H23NO5 |
| HBA | 6 |
| HBD | 1 |
| MW | 333.38 |
| Rotatable Bonds | 0 |
| TPSA | 76.07 |
| LogP | 1.11 |
| Number Rings | 3 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 333.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Senecio abrotanifolius | Asteraceae-Compositae | Plantae | 189225 |
| 2 | Senecio adonidifolius | Asteraceae-Compositae | Plantae | 189226 |
| 3 | Senecio boissieri | Asteraceae-Compositae | Plantae | 214893 |
| 4 | Senecio carniolicus | Asteraceae-Compositae | Plantae | 189240 |
| 5 | Senecio halleri | Asteraceae-Compositae | Plantae | 214899 |
| 6 | Senecio incanus | Asteraceae-Compositae | Plantae | 189239 |
| 7 | Senecio leucophyllus | Asteraceae-Compositae | Plantae | 214900 |
| 8 | Senecio minutus | Asteraceae-Compositae | Plantae | 189241 |
| 9 | Senecio persoonii | Asteraceae-Compositae | Plantae | 214902 |
| 10 | Senecio cannabifolius | Asteraceae-Compositae | Plantae | 189232 |
| 11 | Senecio delphinifolius | Asteraceae-Compositae | Plantae | 214896 |
| 12 | Senecio othonnae | Asteraceae-Compositae | Plantae | 214901 |
| 13 | Senecio paludosus | Asteraceae-Compositae | Plantae | 189244 |
| 14 | Senecio alpinus | Asteraceae-Compositae | Plantae | 189227 |
| 15 | Senecio ambiguus | Asteraceae-Compositae | Plantae | 189228 |
| 16 | Senecio aquaticus | Asteraceae-Compositae | Plantae | 189230 |
| 17 | Senecio chrysanthemoides | Asteraceae-Compositae | Plantae | 189235 |
| 18 | Senecio cineraria | Asteraceae-Compositae | Plantae | 252537 |
| 19 | Senecio erucifolius | Asteraceae-Compositae | Plantae | 189238 |
| 20 | Senecio giganteus | Asteraceae-Compositae | Plantae | 214897 |
| 21 | Senecio gnaphalodes | Asteraceae-Compositae | Plantae | 2868836 |
| 22 | Senecio jacobaea | Asteraceae-Compositae | Plantae | 98722 |
| 23 | Senecio pancicii | Asteraceae-Compositae | Plantae | 189245 |
| 24 | Senecio subalpinus | Asteraceae-Compositae | Plantae | 189250 |
| 25 | Solanecio angulatus | Asteraceae-Compositae | Plantae | 1670880 |
| 26 | Solanecio mannii | Asteraceae-Compositae | Plantae | — |
| 27 | Solanecio tuberosus var. tuberosus | Asteraceae-Compositae | Plantae | 189251 |
Showing of synonyms
Seneciphylline
480-81-9
Seneciphyllin
Jacodine
Seniciphylline
Seneciophylline
ALPHA-LONGILOBINE
13,19-Didehydro-12-hydroxysenecionan-11,16-dione
NSC 30622
UNII-0ZYZ9L5454
CCRIS 4336
HSDB 5188
0ZYZ9L5454
NCI-C61165
NSC-30622
.ALPHA.-LONGILOBINE
SENECIPHYLLINE [MI]
SENECIPHYLLINE [HSDB]
SENECIPHYLLINE [IARC]
(1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
DTXSID8026016
Senecionan-11,16-dione, 13,19-didehydro-12-hydroxy-
Trans-15-Ethylidene-12beta-hydroxy-12alpha-methyl-13-methylenesenec-1-enine
SENECIPHYLLINE (IARC)
(3Z,6R,14AR,14BR)-3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-6-METHYL-5-METHYLENE(1,6)DIOXACYCLODODECINO(2,3,4-GH)PYRROLIZINE-2,7-DIONE
((5S,7R)-5-acetoxy-7-((E)-2-methylbut-2-enoyl)oxy-6,7-dihydro-5H-pyrrolizin-1-yl)methyl (E)-2-(3-methylbut-2-enoyloxymethyl)but-2-enoate
(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-6-METHYL-5-METHYLENE-, (6R-(3Z,6R*,14AR*,14BR*))-
(1R,4Z,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylidene-2,9-dioxa-14-azatricyclo(9.5.1.014,17)heptadec-11-ene-3,8-dione
[(5S,7R)-5-acetoxy-7-[(E)-2-methylbut-2-enoyl]oxy-6,7-dihydro-5H-pyrrolizin-1-yl]methyl (E)-2-(3-methylbut-2-enoyloxymethyl)but-2-enoate
[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-6-METHYL-5-METHYLENE-, [6R-(3Z,6R*,14AR*,14BR*)]-
DTXCID306016
Pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene(1,6)dioxacyclododecino(2,3,4-gh)-
13,19-DIDEHYDRO-12-HYDROXYSENECIONIN-11,16-DIONE
Senecionan-11,16-dione, 13,19-didehydro-12-hydroxy-(9CI)
SENECIONIN-11,16-DIONE, 13,19-DIDEHYDRO-12-HYDROXY-
TRANS-15-ETHYLIDINE-12 BETA-HYDROXY-12 ALPHA-METHYL-13-METHYLENESENEC-1-ENINE
PYRROLIZINE-2,7-DIONE, 3-ETHYLIDENE-3,4,5,6,9,11,13,14,14A,14B-DECAHYDRO-6-HYDROXY-6-METHYL-5-METHYLENE(1,6)DIOXACYCLODODE///
Fcevnjiuimlvml-uuilkarusa-n
NSC30622
CHEBI:9108
[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-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-
C18H23NO5
MLS000737616
Seneciphylline, analytical standard
SMR000393787
Seneciphynine
Prestwick_446
Prestwick2_000599
Prestwick3_000599
Seneciphylline (Standard)
BSPBio_000478
MLS002222214
SCHEMBL177867
BPBio1_000526
CHEMBL523911
CHEBI:92677
HY-N1282R
FCEVNJIUIMLVML-QPSVUOIXSA-N
HMS1569H20
HMS2096H20
HMS2763J21
(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-6-methyl-5-methylene-, (3Z,6R,14aR,14bR)-
HY-N1282
MSK14177
BDBM50480273
EX-A11101
MFCD00221722
AKOS024282719
Seneciphylline 100 microg/mL in Water
NCGC00017384-04
NCGC00142562-03
(1R,7R,17R)-4-ethylidene-7-hydroxy-7-methyl-6-methylene-2,9-dioxa-14-azatricyc lo[9.5.1.0<14,17>]heptadec-11-ene-3,8-dione
1ST14177
AC-34599
DA-57794
FS161595
MS-25026
CS-0016686
Senecionan-11, 13,19-didehydro-12-hydroxy-
(Z)-ethylidene-hydroxy-methyl-methylene-[?]dione
BRD-K38449220-001-03-8
Q27108272
2H-Pyran-2-carboxylicacid,5-ethyltetrahydro-2,3-dimethyl-6-oxo-(9ci)
(3Z,6R,14aR,14bR)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,11,13,14,14a,14b-decahydro[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
(6R,9a1R,14aR,Z)-3-ethylidene-6-hydroxy-6-methyl-5-methylene-3,4,5,6,9,9a1,11,13,14,14a-decahydro-[1,6]dioxacyclododecino[2,3,4-gh]pyrrolizine-2,7-dione
Pyrrolizine-2, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-6-methyl-5-methylene(1,6)dioxacyclododecino[2,3,4-gh]-
- 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]
Pubchem:
5281750
Cas:
480-81-9
Gnps:
CCMSLIB00000213916
Zinc:
ZINC000095627757
Kegg Ligand:
C10391
Chebi:
9108
Nmrshiftdb2:
60068827
Metabolights:
MTBLC9108
Chembl:
CHEMBL523911
Comptox:
DTXSID8026016
Bindingdb:
50480273
CPRiL:
31807
SMILES: C1OC(=O)CC(=C)CC(=C)C(=O)OC(C2C1=3)CCN2CC3
Level: 0
Mol. Weight: 289.33 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.82
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.9
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.83
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.58
- Plasma Protein Binding
- 34.48
- 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
- 5.03
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.04
- Biodegradation
- Toxic
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.04
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 8.15
- 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
- -4.31
- Rat (Acute)
- 3.71
- Rat (Chronic Oral)
- 1.79
- Fathead Minnow
- 3.97
- 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
- 371.21
- Hydration Free Energy
- -8.26
- Log(D) at pH=7.4
- 1.07
- Log(P)
- 0.77
- Log S
- -1.99
- Log(Vapor Pressure)
- -7.43
- Melting Point
- 181.61
- pKa Acid
- 5.88
- pKa Basic
- 6.89
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8982 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.8982 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8672 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8672 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8662 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.8662 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8047 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.8047 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7920 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7920 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7820 |
| Fatty acid-binding protein, liver | P80226 | FABPL_CHICK | Gallus gallus | 3 | 0.7820 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7739 |
| Nuclear receptor subfamily 1 group I member 2 | O75469 | NR1I2_HUMAN | Homo sapiens | 3 | 0.7739 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7616 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 3 | 0.7616 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7558 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7558 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7546 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7546 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7470 |
| Abscisic acid receptor PYL10 | Q8H1R0 | PYL10_ARATH | Arabidopsis thaliana | 3 | 0.7470 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7410 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7410 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7395 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7395 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7386 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7386 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7352 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7352 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 4 | 0.7268 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 4 | 0.7268 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7199 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7199 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7147 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7147 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7106 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 3 | 0.7106 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7093 |
| Abscisic acid receptor PYR1 | O49686 | PYR1_ARATH | Arabidopsis thaliana | 3 | 0.7093 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7062 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7062 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7043 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7043 |