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Cytisine
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
- Class: Alkaloid
| Canonical Smiles | O=c1cccc2n1C[C@@H]1CNC[C@H]2C1 |
|---|---|
| InChI | InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1 |
| InChIKey | ANJTVLIZGCUXLD-DTWKUNHWSA-N |
| Formula | C11H14N2O |
| HBA | 3 |
| HBD | 1 |
| MW | 190.25 |
| Rotatable Bonds | 0 |
| TPSA | 34.03 |
| LogP | 0.55 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.55 |
| Exact Mass | 190.11 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Dicraeopetalum stipulare | Leguminosae/Fabaceae | Plantae | 149649 |
Showing of synonyms
Cytisine
Cytisinicline
Baptitoxin
Laburnin
Tabex
Ulexine
(-)-Cytisine
Cytisin
Tabax
6039 Sopharma
(1r,5s)-1,2,3,4,5,6-Hexahydro-8h-1,5-Methanopyrido[1,2-A][1,5]diazocin-8-One
Citisiniclina
HSDB 3560
EINECS 207-616-0
NSC 407282
NSC-407282
UNII-53S5U404NU
BRN 0083882
CHEBI:4055
53S5U404NU
5-24-02-00535 (Beilstein Handbook Reference)
CYTISINE (MART.)
CYTISINE [MART.]
Citizine
Cystisin
(1R,5S)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO-(1,2-A)(1,5)DIAZOCIN-8-ONE
(1R,5S)-1,2,3,4,5,6-HEXAHYDRO-8H-1,5-METHANOPYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE (CYTISINE)
Cytisiniclinum
(1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido(1,2-a)(1,5)diazocin-8-one
(1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido-(1,2-a)(1,5)diazocin-8-one
1,5-methano-8h-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1r)-
485-35-8
Baptitoxine
Sophorine
Cytiton
Ulexin
Cytitone
Tsitizin
Cystisine
Cytizin
Citizin
Cytisine (-)
(1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one
1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
Cytisinicline [USAN]
CHEMBL497939
(1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-
Baphitoxine
MFCD00136048
(1R,9S)-7,11-diazatricyclo[7.3.1.0^{2,7}]trideca-2,4-dien-6-one
SMR001233264
MLS003171607
NSC407282
(1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido[1,2a][1,5]diazocin-8-one
C5E
Prestwick_140
Cytisine ((+)-)
Tocris-1390
CYTISINE [HSDB]
CYTISINE [MI]
Cytisinicline (Standard)
115051-74-6
Prestwick3_000624
(?)-Cytisine
CYTISINICLINE [INN]
BSPBio_000588
Cytisine, >=99%, powder
MLS002153916
MLS002222174
SCHEMBL161398
CYTISINICLINE [WHO-DD]
BPBio1_000648
GTPL5347
(1R,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
(1S,9R)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
HY-N0175R
DTXSID00883395
1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one (cytisine)
Cytisine1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
HMS2096N10
HMS2235L06
HMS3267D20
HMS3414N03
HMS3678L21
HMS3884L11
HY-N0175
MSK40318
TNP00030
BDBM50143282
HB2033
PDSP1_000461
S2287
WLN: T C666 A GVN LM&TTJ
1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one
AKOS000276818
AKOS015833102
CCG-208621
DB09028
FC09851
NCGC00016463-01
NCGC00016463-02
NCGC00016463-03
NCGC00016463-04
NCGC00017171-01
NCGC00025138-01
NCGC00025138-02
NCGC00179513-01
AC-34317
AS-19539
CAS-485-35-8
CS-0007888
NS00067015
SW219952-1
Cytisine, >=99.0% (HPLC), >=99%
EN300-224852
Q417343
BRD-K74186897-001-02-5
BRD-K74186897-001-04-1
BRD-K74186897-001-10-8
BRD-K74186897-001-11-6
BRD-K74186897-001-12-4
BRD-K74186897-001-13-2
F9994-5373
Z1203159860
1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-
1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R)-
(1R,9S)-7,11-diazatricyclo[7.3.1.0,2,7]trideca-2,4-dien-6-one
(1R,9S)-7,11-diazatricyclo[7.3.1.0~2,7~]trideca-2,4-dien-6-one
1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R-cis)-
(1R,5S)-1,2,3,4,5,6-Hexahydro-1,5-methano-pyrido[1,2-a][1,5]diazocin-8-one
Pubchem:
10235
Cas:
485-35-8
Gnps:
CCMSLIB00000204761
Zinc:
ZINC000001599730
Chebi:
4055
Nmrshiftdb2:
60025382
Metabolights:
MTBLC4055
Chembl:
CHEMBL497939
Comptox:
DTXSID00883395
Drugbank:
DB09028
Pdb Ligand:
C5E
Selleck:
Cytisine(Baphitoxine,-Sophorine)
CPRiL:
31837
SMILES: c1ccc(=O)n(c12)CC3CC2CNC3
Level: 0
Mol. Weight: 190.25 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.27
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.800
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.03
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.200
- Plasma Protein Binding
- 41.69
- 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
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 7.140
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.050
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.090
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.140
- 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
- -0.810
- Rat (Acute)
- 2.760
- Rat (Chronic Oral)
- 1.550
- Fathead Minnow
- 3.540
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 334.440
- Hydration Free Energy
- -8.780
- Log(D) at pH=7.4
- -0.110
- Log(P)
- 0.03
- Log S
- 0.34
- Log(Vapor Pressure)
- -6.17
- Melting Point
- 189.23
- pKa Acid
- 5.78
- pKa Basic
- 8.88
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 3 | 0.9455 |
| Trichodiene synthase | P13513 | TRI5_FUSSP | Fusarium sporotrichioides | 3 | 0.9455 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.9184 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.9184 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8828 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8828 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8406 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 3 | 0.8406 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8404 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.8404 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8160 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.8160 |
| Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.8047 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8047 |
| 11-beta-hydroxysteroid dehydrogenase 1 | P50172 | DHI1_MOUSE | Mus musculus | 3 | 0.8047 |
| Acetylcholine-binding protein | P58154 | ACHP_LYMST | Lymnaea stagnalis | 3 | 0.8047 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7975 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7975 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7852 |
| Bifunctional dihydrofolate reductase-thymidylate synthase | P13922 | DRTS_PLAFK | Plasmodium falciparum | 2 | 0.7852 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7808 |
| Nuclear receptor ROR-gamma | P51449 | RORG_HUMAN | Homo sapiens | 2 | 0.7808 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7759 |
| Ferrochelatase, mitochondrial | P22830 | HEMH_HUMAN | Homo sapiens | 2 | 0.7759 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7733 |
| Succinate dehydrogenase flavoprotein subunit | P0AC41 | SDHA_ECOLI | Escherichia coli | 3 | 0.7733 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7719 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7719 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 2 | 0.7713 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 2 | 0.7713 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7554 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7554 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7515 |
| Acetylcholinesterase | P21836 | ACES_MOUSE | Mus musculus | 2 | 0.7515 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7503 |
| Prostaglandin reductase 2 | Q8N8N7 | PTGR2_HUMAN | Homo sapiens | 2 | 0.7503 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7440 |
| Abscisic acid receptor PYL3 | Q9SSM7 | PYL3_ARATH | Arabidopsis thaliana | 3 | 0.7440 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7423 |
| Progesterone receptor | P06401 | PRGR_HUMAN | Homo sapiens | 2 | 0.7423 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7420 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7420 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7407 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7407 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7350 |
| Sulfotransferase 2A1 | Q06520 | ST2A1_HUMAN | Homo sapiens | 2 | 0.7350 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7336 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7336 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7312 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.7312 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7259 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7259 |
| 3-alpha-hydroxysteroid dehydrogenase | P23457 | DIDH_RAT | Rattus norvegicus | 2 | 0.7259 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7259 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7256 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 2 | 0.7256 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7241 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7241 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7240 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7240 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7235 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7235 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 2 | 0.7219 |
| Neocarzinostatin | P0A3R9 | NCZS_STRCZ | Streptomyces carzinostaticus | 2 | 0.7219 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7219 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7219 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7216 |
| Nuclear receptor ROR-beta | P45446 | RORB_RAT | Rattus norvegicus | 2 | 0.7216 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7215 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7215 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7215 |
| Fatty acid-binding protein 10-A, liver basic | Q9I8L5 | FA10A_DANRE | Danio rerio | 2 | 0.7215 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7210 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7210 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7210 |
| Aldo-keto reductase family 1 member C2 | P52895 | AK1C2_HUMAN | Homo sapiens | 2 | 0.7210 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7197 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 2 | 0.7197 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7190 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7190 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7183 |
| CmeR | Q7B8P6 | Q7B8P6_CAMJU | Campylobacter jejuni | 2 | 0.7183 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7134 |
| Gastrotropin | Q6IMW5 | Q6IMW5_DANRE | Danio rerio | 2 | 0.7134 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7094 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 2 | 0.7094 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7092 |
| Steroid Delta-isomerase | P07445 | SDIS_PSEPU | Pseudomonas putida | 2 | 0.7092 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7049 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7049 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7046 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 2 | 0.7046 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7043 |
| Steroid 21-hydroxylase | P08686 | CP21A_HUMAN | Homo sapiens | 2 | 0.7043 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7036 |
| Abscisic acid receptor PYL2 | O80992 | PYL2_ARATH | Arabidopsis thaliana | 2 | 0.7036 |