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N-methylflindersine

Family: Plantae - Rutaceae
Kingdom: Plantae
Class: Alkaloid

Canonical Smiles	Cn1c(=O)c2C=CC(Oc2c2c1cccc2)(C)C
InChI	InChI=1S/C15H15NO2/c1-15(2)9-8-11-13(18-15)10-6-4-5-7-12(10)16(3)14(11)17/h4-9H,1-3H3
InChIKey	RJZFGBNKPOVCHQ-UHFFFAOYSA-N
Formula	C₁₅H₁₅NO₂
HBA	3
HBD	0
MW	241.29
Rotatable Bonds	0
TPSA	31.23
LogP	2.72
Number Rings	3
Number Aromatic Rings	2
Heavy Atom Count	18
Formal Charge	0
Fraction CSP3	0.27
Exact Mass	241.11
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Fagara chalybea and Fagara holtziana	Rutaceae	Plantae	1237852

Showing of synonyms

Taniguchi M, Kubo I. (1993). Ethnobotanical drug discovery based on medicine men's trials in the African savanna: screening of east African plants for antimicrobial activity II.. Journal of Natural Products,1993,56(9),1539-1546. [View] [PubMed]

Pubchem: 72819

Cas: 50333-13-6

Zinc: ZINC000000900263

Kegg Ligand: C10731

Chebi: 7315

Nmrshiftdb2: 60004533

Chembl: CHEMBL400130

Comptox: DTXSID40198374

CPRiL: 412517

SMILES: O1CC=Cc(c1c23)c(=O)[nH]c2cccc3

Level: 0

Mol. Weight: 241.29 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp): -4.71
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.2
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -1.96

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.97
Plasma Protein Binding: 36.91
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Inhibitor
CYP 2C19 Substrate: Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: 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: 6.66
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.35
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.96
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.44
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: 3.74
Rat (Acute): 3.04
Rat (Chronic Oral): 1.78
Fathead Minnow: 4.49
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: 369.08
Hydration Free Energy: -9.27
Log(D) at pH=7.4: 2.98
Log(P): 2.81
Log S: -3.51
Log(Vapor Pressure): -5.74
Melting Point: 164.58
pKa Acid: 7.46
pKa Basic: 4.73

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8406
Casein kinase II subunit alpha	P28523	CSK2A_MAIZE	Zea mays	3	0.8406
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8129
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8129
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8075
Cyclin-dependent kinase 2	P24941	CDK2_HUMAN	Homo sapiens	3	0.8075
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8065
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.8065
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7887
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7887
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7864
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	2	0.7864
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7863
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7863
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7773
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7773
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7728
Aldo-keto reductase family 1 member B10	O60218	AK1BA_HUMAN	Homo sapiens	3	0.7728
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7680
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7680
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7565
Gag-Pol polyprotein	P04585	POL_HV1H2	Human immunodeficiency virus type 1 group M subtype B	3	0.7565
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7496
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	3	0.7496
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7313
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7313
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7246
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.7246
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7216
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	2	0.7216
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7213
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7213
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7194
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	2	0.7194
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7175
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7175
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7148
Albumin	P02768	ALBU_HUMAN	Homo sapiens	3	0.7148
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7140
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7140
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7129
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	2	0.7129
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7093
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7093
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7087
3',5'-cyclic-AMP phosphodiesterase 4A	P27815	PDE4A_HUMAN	Homo sapiens	3	0.7087
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7052
Aldo-keto reductase family 1 member B1	P80276	ALDR_PIG	Sus scrofa	3	0.7052
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7037
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	4	0.7037

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