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N-methylcytisine

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

Canonical Smiles	O=CN1CC2CC(C1)c1n(C2)c(=O)ccc1
InChI	InChI=1S/C12H14N2O2/c15-8-13-5-9-4-10(7-13)11-2-1-3-12(16)14(11)6-9/h1-3,8-10H,4-7H2
InChIKey	PCYQRXYBKKZUSR-UHFFFAOYSA-N
Formula	C₁₂H₁₄N₂O₂
HBA	3
HBD	0
MW	218.26
Rotatable Bonds	1
TPSA	42.31
LogP	0.42
Number Rings	3
Number Aromatic Rings	1
Heavy Atom Count	16
Formal Charge	0
Fraction CSP3	0.5
Exact Mass	218.11
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: 589870

Gnps: CCMSLIB00009919253

Nmrshiftdb2: 60025420

Chembl: CHEMBL1433686

CPRiL: 39908

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

Level: 0

Mol. Weight: 218.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -5.01
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.4
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): 0.32
Plasma Protein Binding: 23.95
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: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 10.11
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.38
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.07
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.64
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: 3.66
Rat (Acute): 2.49
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: 361.98
Hydration Free Energy: -9.11
Log(D) at pH=7.4: 0.02
Log(P): -0.32
Log S: -0.36
Log(Vapor Pressure): -7.03
Melting Point: 147.9
pKa Acid: 6.98
pKa Basic: 4.65

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8938
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8938
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8635
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8635
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8427
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8427
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8204
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.8204
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8037
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8037
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7905
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7905
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7896
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7896
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7782
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7782
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7752
Progesterone receptor	P06401	PRGR_HUMAN	Homo sapiens	2	0.7752
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7695
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7695
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7682
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7682
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	2	0.7678
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	2	0.7678
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7640
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7640
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7471
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7471
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7465
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.7465
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7461
glutaryl-CoA dehydrogenase (ETF)	Q3JP94	Q3JP94_BURP1	Burkholderia pseudomallei	2	0.7461
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7435
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7435
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7426
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7426
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7391
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7391
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7390
Nuclear receptor ROR-gamma	P51449	RORG_HUMAN	Homo sapiens	2	0.7390
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7386
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7386
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7373
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	2	0.7373
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7371
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7371
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7330
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7330
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7310
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	2	0.7310
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7255
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7255
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7227
DNA-directed DNA polymerase	Q38087	DPOL_BPR69	Escherichia phage RB69	2	0.7227
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7221
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7221
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7194
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7194
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7174
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	2	0.7174
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	2	0.7172
Steroid 21-hydroxylase	P08686	CP21A_HUMAN	Homo sapiens	2	0.7172
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7151
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7151
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7145
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	2	0.7145
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7120
Ribosyldihydronicotinamide dehydrogenase [quinone]	P16083	NQO2_HUMAN	Homo sapiens	3	0.7120
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7089
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7089
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7085
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7085
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7055
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7055
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7036
1-deoxy-D-xylulose 5-phosphate reductoisomerase	P45568	DXR_ECOLI	Escherichia coli	2	0.7036
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7028
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.7028

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