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N-acetylcytisine

Family: Plantae - Leguminosae/Fabaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	CC(=O)N1CC2CC(C1)c1n(C2)c(=O)ccc1
InChI	InChI=1S/C13H16N2O2/c1-9(16)14-6-10-5-11(8-14)12-3-2-4-13(17)15(12)7-10/h2-4,10-11H,5-8H2,1H3
InChIKey	WCRIKJOQMRFVPX-UHFFFAOYSA-N
Formula	C₁₃H₁₆N₂O₂
HBA	3
HBD	0
MW	232.28
Rotatable Bonds	0
TPSA	42.31
LogP	0.81
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	17
Formal Charge	0
Fraction CSP3	0.54
Exact Mass	232.12
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Dicraeopetalum stipulare	Leguminosae/Fabaceae	Plantae	149649

Showing of synonyms

Asres K, Tei A, et al. (1997). Quinolizidine alkaloids from the east-african legume Dicraeopetalum stipulare harms.. Biochemical Systematics and Ecology,1997,25(4),305-308. [View] [PubMed]

Pubchem: 3716901

Cas: 109120-10-7

Chebi: 181846

Nmrshiftdb2: 60025422

Chembl: CHEMBL1513538

No compound-protein relationship available.

SMILES: c1ccc(=O)n(c12)CC3CC2CNC3

Level: 0

Mol. Weight: 232.28 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.96
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.36
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.78

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.3
Plasma Protein Binding: 26.57
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: 9.29
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.54
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: -0.01
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.84
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: 3.29
Rat (Acute): 2.56
Rat (Chronic Oral): 1.59
Fathead Minnow: 3.44
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: 356.57
Hydration Free Energy: -9.53
Log(D) at pH=7.4: -0.07
Log(P): -0.17
Log S: -0.55
Log(Vapor Pressure): -6.75
Melting Point: 157.63
pKa Acid: 6.76
pKa Basic: 5.68

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9089
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9089
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8842
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8842
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8697
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.8697
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7920
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7920
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7905
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7905
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7873
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7873
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7784
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7784
Nucleoside permease	Q9KPL5	Q9KPL5_VIBCH	Vibrio cholerae serotype O1	3	0.7760
Nucleoside permease	Q9KPL5	Q9KPL5_VIBCH	Vibrio cholerae serotype O1	3	0.7760
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7757
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7757
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7730
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7730
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7728
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7728
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7696
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7696
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7666
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7666
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7654
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7654
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7605
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7605
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7571
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7571
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7569
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7569
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7543
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7543
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7534
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7534
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7512
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7512
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7479
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7479
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	2	0.7442
NPC intracellular cholesterol transporter 1	O15118	NPC1_HUMAN	Homo sapiens	2	0.7442
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7434
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7434
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7434
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7434
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7408
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7408
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7391
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7391
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7389
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7389
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	2	0.7387
3-hydroxybenzoate 4-monooxygenase	Q6SSJ6	MOBA_COMTE	Comamonas testosteroni	2	0.7387
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7384
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7384
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7382
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7382
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7371
cGMP-dependent protein kinase 1	Q13976	KGP1_HUMAN	Homo sapiens	2	0.7371
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7370
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7370
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7360
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7360
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7334
Orotidine 5'-phosphate decarboxylase	Q5L0U0	PYRF_GEOKA	Geobacillus kaustophilus	3	0.7334
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7318
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7318
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7305
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7305
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7291
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7291
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7282
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	2	0.7282
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7279
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7279
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7270
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7270
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7269
Bifunctional dihydrofolate reductase-thymidylate synthase	P13922	DRTS_PLAFK	Plasmodium falciparum	2	0.7269
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7223
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7223
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7179
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7179
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7170
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7170
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7169
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7169
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7163
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7163
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7159
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7159
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7154
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7154
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7151
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7151
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7147
cAMP-dependent protein kinase type I-alpha regulatory subunit	P00514	KAP0_BOVIN	Bos taurus	2	0.7147
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7125
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7125
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7109
Abscisic acid receptor PYL2	O80992	PYL2_ARATH	Arabidopsis thaliana	2	0.7109
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7095
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7095
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.7091
Probable esterase KAI2	Q9SZU7	KAI2_ARATH	Arabidopsis thaliana	3	0.7091
Kynurenine 3-monooxygenase	P38169	KMO_YEAST	Saccharomyces cerevisiae	2	0.7082
Kynurenine 3-monooxygenase	P38169	KMO_YEAST	Saccharomyces cerevisiae	2	0.7082
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7076
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7076
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7070
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7070
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7065
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7065
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7061
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	2	0.7061
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7060
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7060
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	2	0.7058
Neutrophil gelatinase-associated lipocalin	P80188	NGAL_HUMAN	Homo sapiens	2	0.7058
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7052
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	2	0.7052
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7047
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7047
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7036
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7036
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	2	0.7025
DNA polymerase III subunit epsilon	P03007	DPO3E_ECOLI	Escherichia coli	2	0.7025
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7023
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7023
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7017
Fatty acid-binding protein 10-A, liver basic	Q9I8L5	FA10A_DANRE	Danio rerio	2	0.7017
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7011
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7011
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7007
Pteridine reductase	O76290	O76290_TRYBB	Trypanosoma brucei brucei	2	0.7007
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7003
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7003

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