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Senkirkine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Pyrrolizidine Alkaloid
| Canonical Smiles | C/C=C\1/C[C@@H](C)[C@@](C)(O)C(=O)OCC2=CCN(CC[C@@H](OC1=O)C2=O)C |
|---|---|
| InChI | InChI=1S/C19H27NO6/c1-5-13-10-12(2)19(3,24)18(23)25-11-14-6-8-20(4)9-7-15(16(14)21)26-17(13)22/h5-6,12,15,24H,7-11H2,1-4H3/b13-5-,14-6?/t12-,15-,19-/m1/s1 |
| InChIKey | HPDHKHMHQGCNPE-QESVCWQLSA-N |
| Formula | C19H27NO6 |
| HBA | 7 |
| HBD | 1 |
| MW | 365.43 |
| Rotatable Bonds | 0 |
| TPSA | 93.14 |
| LogP | 1.01 |
| Number Rings | 2 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.63 |
| Exact Mass | 365.18 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Senecio carniolicus | Asteraceae | Plantae | 189240 |
| 2 | Senecio halleri | Asteraceae | Plantae | 214899 |
| 3 | Senecio leucophyllus | Asteraceae | Plantae | 214900 |
| 4 | Senecio minutus | Asteraceae | Plantae | 189241 |
| 5 | Senecio delphinifolius | Asteraceae | Plantae | 214896 |
| 6 | Senecio othonnae | Asteraceae | Plantae | 214901 |
| 7 | Senecio chrysanthemoides | Asteraceae | Plantae | 189235 |
| 8 | Senecio gnaphalodes | Asteraceae | Plantae | 2868836 |
| 9 | Crotalaria laburnifolia | Leguminosae/Fabaceae | Plantae | 992673 |
| 10 | Crotalaria phillipsiae | Leguminosae/Fabaceae | Plantae | 3086461 |
Showing of synonyms
Senkirkine
2318-18-5
SENKIRKIN
Renardin
UNII-X65P7V4LVJ
X65P7V4LVJ
NSC-89945
Senkarkane
CCRIS 557
HSDB 3536
Senkirkine (neutral)
DTXSID4021266
2,12-Dihydroxy-4-methyl-11,16-dioxosenecionanium
12-Hydroxy-4-methyl-4,8-secosenecionan-8,11,16-trione
4,8-Secosenecionan-8,11,16-trione, 12-hydroxy-4-methyl-
SENKIRKINE (IARC)
SENKIRKINE [IARC]
Trans-15-Ethylidene-12-beta-hydroxy-4,12-alpha,13-beta-trimethyl 8-oxo-4,8 secosenec-1-enine
(1R,4Z,6R,7R)-4-ETHYLIDENE-7-HYDROXY-6,7,14-TRIMETHYL-2,9-DIOXA-14-AZABICYCLO(9.5.1)HEPTADEC-11-ENE-3,8,17-TRIONE
2,9-DIOXA-14-AZABICYCLO(9.5.1)HEPTADEC-11-ENE-3,8,17-TRIONE, 4-ETHYLIDENE-7-HYDROXY-6,7,14-TRIMETHYL-, (1R,4Z,6R,7R)-
DTXCID701266
Trans-15-ethylidene-12-beta-hydroxy-4,12-alpha,13-beta-trimethyl-8-oxp-4,8-secosenec-1-enine
CHEBI:9111
CHEMBL470059
(1R,4Z,6R,7R,11Z)-4-ethylidene-7-hydroxy-6,7,14-trimethyl-2,9-dioxa-14-azabicyclo[9.5.1]heptadec-11-ene-3,8,17-trione
AC1NQZ0B
Renardine (neutral) (VAN)
Senkirkine (neutral) (VAN)
MFCD01684247
Senkirkine, analytical standard
MSK14181
Senkirkine 100 microg/mL in Water
1ST14181
DA-77796
FS161626
HY-122509
CS-0085930
NS00098511
Q27108274
- 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. (2004). Patterns of pyrrolizidine alkaloids in 12 Ethiopian Crotalaria species.. Biochemical systematics and ecology,2004,32(10),915-930. [View] [PubMed]
Pubchem:
5281752
Cas:
2318-18-5
Gnps:
CCMSLIB00005770506
Kegg Ligand:
C10396
Chebi:
9111
Nmrshiftdb2:
60033876
Chembl:
CHEMBL470059
Comptox:
DTXSID4021266
CPRiL:
80937
SMILES: C1OC(=O)CCCC(=C)C(=O)OC(C2=O)CCNCC=C12
Level: 0
Mol. Weight: 365.43 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.79
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.84
- Human Oral Bioavailability 50%
- Non-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)
- 0.48
- Plasma Protein Binding
- 31.21
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- 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
- 7.6
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.6
- Biodegradation
- Safe
- Carcinogenesis
- Toxic
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.89
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 9.26
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -5.73
- Rat (Acute)
- 3.29
- Rat (Chronic Oral)
- 1.56
- Fathead Minnow
- 3.99
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 381.71
- Hydration Free Energy
- -11.09
- Log(D) at pH=7.4
- 1.35
- Log(P)
- 0.86
- Log S
- -1.53
- Log(Vapor Pressure)
- -8.09
- Melting Point
- 174.56
- pKa Acid
- 5.71
- pKa Basic
- 5.93
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.9011 |
| Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 | P04191 | AT2A1_RABIT | Oryctolagus cuniculus | 3 | 0.9011 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8044 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.8044 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7998 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7998 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7937 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7937 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7840 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7840 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7817 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7817 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7816 |
| Androgen receptor | P10275 | ANDR_HUMAN | Homo sapiens | 3 | 0.7816 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7687 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 2 | 0.7687 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7687 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7687 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7642 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7642 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7608 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7608 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7449 |
| Mycinamicin III 3''-O-methyltransferase | Q49492 | MYCF_MICGR | Micromonospora griseorubida | 3 | 0.7449 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7407 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7407 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7374 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7374 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7340 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7340 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 3 | 0.7340 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7340 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7314 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7314 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7293 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7293 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7131 |
| Aldo-keto reductase family 1 member C3 | P42330 | AK1C3_HUMAN | Homo sapiens | 3 | 0.7131 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7086 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7086 |