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8-cyanopalmatine

Family: Plantae - Annonaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Protoberberine Alkaloid

Canonical Smiles	COc1cc2CCN3[C@H](c2cc1OC)Cc1c(C3C#N)c(OC)c(cc1)OC
InChI	InChI=1S/C22H24N2O4/c1-25-18-6-5-14-9-16-15-11-20(27-3)19(26-2)10-13(15)7-8-24(16)17(12-23)21(14)22(18)28-4/h5-6,10-11,16-17H,7-9H2,1-4H3/t16-,17?/m0/s1
InChIKey	CWLFISBXVVVSDA-BHWOMJMDSA-N
Formula	C₂₂H₂₄N₂O₄
HBA	6
HBD	0
MW	380.44
Rotatable Bonds	4
TPSA	63.95
LogP	3.44
Number Rings	4
Number Aromatic Rings	2
Heavy Atom Count	28
Formal Charge	0
Fraction CSP3	0.41
Exact Mass	380.17
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Enantia chlorantha	Annonaceae	Plantae	306909

Showing of synonyms

Nkwengoua ET, Ngantchou I, et al. (2009). In vitro inhibitory effects of palmatine from Enantia chlorantha on Trypanosoma cruzi and Leishmania infantum. Natural product research,2009, 23(12), 1144-1150. [View] [PubMed]

No compound-protein relationship available.

SMILES: c1cccc(c12)CCN3C2Cc4c(C3)cccc4

Level: 0

Mol. Weight: 380.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.86
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.610
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.1

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.860
Plasma Protein Binding: 52.56
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Inhibitor
CYP 1A2 Substrate: Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 8.430
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 1.840
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Toxic
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.020
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 10.170
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: -17.360
Rat (Acute): 2.920
Rat (Chronic Oral): 1.300
Fathead Minnow: 5.090
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: 446.640
Hydration Free Energy: -6.210
Log(D) at pH=7.4: 2.160
Log(P): 2.55
Log S: -2.46
Log(Vapor Pressure): -8.33
Melting Point: 168.77
pKa Acid: 10.49
pKa Basic: 6.81

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.9551
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.9231
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	3	0.9186
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.9115
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8956
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8904
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8878
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8796
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8620
Death-associated protein kinase 1	P53355	DAPK1_HUMAN	Homo sapiens	4	0.8516
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8454
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8383
Rhodopsin kinase GRK1	P28327	GRK1_BOVIN	Bos taurus	3	0.8234
NADH:flavin oxidoreductase Sye1	Q8EEC8	Q8EEC8_SHEON	Shewanella oneidensis	3	0.8185
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.8163
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.8153
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8102
Steroid C26-monooxygenase	P9WPP1	CP125_MYCTU	Mycobacterium tuberculosis	3	0.8063
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.8023
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8011
Protein LlR18A	P52778	L18A_LUPLU	Lupinus luteus	3	0.8007
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7999
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7979
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	3	0.7956
Metapyrocatechase	Q7WYF5	Q7WYF5_9PSED	Pseudomonas alkylphenolica	3	0.7956
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7869
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	4	0.7863
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7847
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7846
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7840
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	3	0.7805
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7800
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7785
Phosphodiesterase	Q8WQX9	Q8WQX9_9TRYP	Trypanosoma brucei	3	0.7782
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1	P04191	AT2A1_RABIT	Oryctolagus cuniculus	3	0.7671
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7660
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7634
Aldo-keto reductase family 1 member B1	P15121	ALDR_HUMAN	Homo sapiens	3	0.7622
Vitamin D3 dihydroxylase	P18326	CPXE_STRGO	Streptomyces griseolus	3	0.7580
Nodulin-13	P93330	NOD13_MEDTR	Medicago truncatula	3	0.7469
Lanosterol 14-alpha demethylase	A6ZSR0	A6ZSR0_YEAS7	Saccharomyces cerevisiae	3	0.7426
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7421
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7407
Gag-Pol polyprotein	P03367	POL_HV1BR	Human immunodeficiency virus type 1 group M subtype B	3	0.7340
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	3	0.7340
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7304
Eugenol synthase 1	Q15GI4	EGS1_OCIBA	Ocimum basilicum	3	0.7227
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.7219
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7204
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	3	0.7185
Glycylpeptide N-tetradecanoyltransferase	Q4Q5S8	Q4Q5S8_LEIMA	Leishmania major	3	0.7171
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7161
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	2	0.7143
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	2	0.7108
Orotidine 5'-phosphate decarboxylase	O26232	PYRF_METTH	Methanothermobacter thermautotrophicus	3	0.7107
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7102
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7101
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7089
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7079
Glycogen synthase	Q9V2J8	Q9V2J8_PYRAB	Pyrococcus abyssi	3	0.7078
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7074
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	2	0.7064
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7064
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7059
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	2	0.7048
Aldo-keto reductase family 1 member A1	P50578	AK1A1_PIG	Sus scrofa	3	0.7043
Streptogramin A acetyltransferase	P50870	VATD_ENTFC	Enterococcus faecium	3	0.7032
Beta-lactamase	Q9L5C8	Q9L5C8_ECOLX	Escherichia coli	3	0.7028
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7023
Casein kinase I isoform gamma-3	Q9Y6M4	KC1G3_HUMAN	Homo sapiens	3	0.7014
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7002

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