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Anisotine

Family: Acanthaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Quinazoline Alkaloid

Canonical Smiles	COC(=O)c1cc(ccc1NC)C1CCn2c1nc1ccccc1c2=O
InChI	InChI=1S/C20H19N3O3/c1-21-16-8-7-12(11-15(16)20(25)26-2)13-9-10-23-18(13)22-17-6-4-3-5-14(17)19(23)24/h3-8,11,13,21H,9-10H2,1-2H3
InChIKey	FZKRWTVMKFSFSG-UHFFFAOYSA-N
Formula	C₂₀H₁₉N₃O₃
HBA	6
HBD	1
MW	349.39
Rotatable Bonds	3
TPSA	73.22
LogP	2.76
Number Rings	4
Number Aromatic Rings	3
Heavy Atom Count	26
Formal Charge	0
Fraction CSP3	0.25
Exact Mass	349.14
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Adhatoda vasica	Acanthaceae	Plantae	141317

Showing of synonyms

Ali S.K, Hamed A.R, et al. (2016). Kinetics and molecular docking of vasicine from Adhatoda vasica: Anacetylcholinesterase inhibitor for Alzheimer's disease. South African Journal of Botany, 2016, 104, 118–124. [View]

Pubchem: 442884

Cas: 16688-19-0

Kegg Ligand: C10639

Chebi: 2738

Nmrshiftdb2: 70058214

Comptox: DTXSID90331991

No compound-protein relationship available.

SMILES: c1cccc(n2)c1c(=O)n(c23)CCC3c4ccccc4

Level: 1

Mol. Weight: 262.31 g/mol

SMILES: C1CCn(c12)c(=O)c3c(n2)cccc3

Level: 0

Mol. Weight: 186.21 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.57
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.720
Human Oral Bioavailability 50%: Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.0

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 1.550
Plasma Protein Binding: 76.37
Steady State Volume of Distribution: -

Metabolism

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

Excretion

Clearance: 7.760
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Toxic
Avian: Safe
Bee: Safe
Bioconcentration Factor: 1.290
Biodegradation: Safe
Carcinogenesis: Toxic
Crustacean: Toxic
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.330
Liver Injury II: Toxic
hERG Blockers: Toxic
Daphnia Maga: 5.490
Micronucleos: Toxic
NR-AhR: Toxic
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: -3.340
Rat (Acute): 2.490
Rat (Chronic Oral): 1.410
Fathead Minnow: 4.890
Respiratory Disease: Toxic
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Toxic
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 472.120
Hydration Free Energy: -7.050
Log(D) at pH=7.4: 2.510
Log(P): 3.22
Log S: -4.93
Log(Vapor Pressure): -9.37
Melting Point: 174.77
pKa Acid: 8.53
pKa Basic: 6.92

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Bromodomain testis-specific protein	Q58F21	BRDT_HUMAN	Homo sapiens	3	0.9312
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9229
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.9193
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9159
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9156
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.9103
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8810
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	3	0.8653
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8642
Cytohesin-2	Q99418	CYH2_HUMAN	Homo sapiens	3	0.8642
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.8635
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8611
Stromelysin-1	P08254	MMP3_HUMAN	Homo sapiens	3	0.8599
Carbonic anhydrase 12	O43570	CAH12_HUMAN	Homo sapiens	3	0.8546
Flavin reductase (NADPH)	P30043	BLVRB_HUMAN	Homo sapiens	3	0.8535
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.8457
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.8416
Prostaglandin E synthase 2	Q9N0A4	PGES2_MACFA	Macaca fascicularis	3	0.8366
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	3	0.8361
Thymidylate synthase	P0A886	TYSY_ECO57	Escherichia coli O157:H7	3	0.8341
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	4	0.8307
Mycocyclosin synthase	P9WPP7	CP121_MYCTU	Mycobacterium tuberculosis	3	0.8178
Genome polyprotein	O92972	POLG_HCVJ4	Hepatitis C virus genotype 1b	3	0.8154
Histamine N-methyltransferase	P50135	HNMT_HUMAN	Homo sapiens	4	0.8088
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.8071
Dicamba O-demethylase, oxygenase component	Q5S3I3	DDMC_STEMA	Stenotrophomonas maltophilia	3	0.8048
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8047
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8046
Matrix metalloproteinase-9	P14780	MMP9_HUMAN	Homo sapiens	3	0.7970
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.7968
Methionine aminopeptidase 2	P9WK19	MAP12_MYCTU	Mycobacterium tuberculosis	3	0.7939
Soluble acetylcholine receptor	Q8WSF8	Q8WSF8_APLCA	Aplysia californica	3	0.7918
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.7907
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7904
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7870
Casein kinase I isoform delta	P48730	KC1D_HUMAN	Homo sapiens	3	0.7861
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7838
Cathepsin S	P25774	CATS_HUMAN	Homo sapiens	3	0.7837
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7822
Mycinamicin III 3''-O-methyltransferase	Q49492	MYCF_MICGR	Micromonospora griseorubida	2	0.7819
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7808
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7804
Endothiapepsin	P11838	CARP_CRYPA	Cryphonectria parasitica	3	0.7786
Protoporphyrinogen oxidase	P50336	PPOX_HUMAN	Homo sapiens	3	0.7777
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase	Q8DNV6	Q8DNV6_STRR6	Streptococcus pneumoniae	3	0.7762
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7743
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7741
Protein S100-A4	P26447	S10A4_HUMAN	Homo sapiens	3	0.7734
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	3	0.7727
Cytochrome P450 1A1	P04798	CP1A1_HUMAN	Homo sapiens	3	0.7716
Peroxisome proliferator-activated receptor gamma	P37231	PPARG_HUMAN	Homo sapiens	3	0.7647
Mitogen-activated protein kinase 8	P45983	MK08_HUMAN	Homo sapiens	3	0.7645
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7642
Calmodulin	P62157	CALM_BOVIN	Bos taurus	3	0.7636
Methionine aminopeptidase	P0AE18	MAP1_ECOLI	Escherichia coli	3	0.7616
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7614
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7609
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7594
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7548
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	2	0.7546
Bromodomain-containing protein 4	O60885	BRD4_HUMAN	Homo sapiens	3	0.7542
Bifunctional dihydrofolate reductase-thymidylate synthase	Q27793	DRTS_TRYCR	Trypanosoma cruzi	4	0.7516
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase	Q6T1W8	FDTA_ANETH	Aneurinibacillus thermoaerophilus	4	0.7510
Aldo-keto reductase family 1 member C3	P42330	AK1C3_HUMAN	Homo sapiens	3	0.7501
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7491
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7489
Cytosolic purine 5'-nucleotidase	P49902	5NTC_HUMAN	Homo sapiens	2	0.7486
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	2	0.7469
Mitogen-activated protein kinase 14	Q16539	MK14_HUMAN	Homo sapiens	4	0.7450
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	4	0.7434
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7431
Camphor 5-monooxygenase	P00183	CPXA_PSEPU	Pseudomonas putida	3	0.7430
Thiamine-phosphate synthase	P39594	THIE_BACSU	Bacillus subtilis	3	0.7422
Gag-Pol polyprotein	P12497	POL_HV1N5	Human immunodeficiency virus type 1 group M subtype B	3	0.7419
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7417
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	4	0.7413
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase	O67060	ISPE_AQUAE	Aquifex aeolicus	3	0.7401
Hypoxanthine phosphoribosyltransferase	Q4DRC4	Q4DRC4_TRYCC	Trypanosoma cruzi	3	0.7400
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7396
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	2	0.7394
Methionine aminopeptidase 2	P50579	MAP2_HUMAN	Homo sapiens	3	0.7383
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7382
4,4'-diapophytoene synthase	A9JQL9	CRTM_STAAU	Staphylococcus aureus	3	0.7382
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7368
Carbonyl reductase [NADPH] 1	P16152	CBR1_HUMAN	Homo sapiens	3	0.7348
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7331
11-beta-hydroxysteroid dehydrogenase 1	Q6QLL4	DHI1_CAVPO	Cavia porcellus	3	0.7325
Casein kinase I isoform delta	P48730	KC1D_HUMAN	Homo sapiens	3	0.7325
Proliferating cell nuclear antigen	P12004	PCNA_HUMAN	Homo sapiens	3	0.7321
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	3	0.7320
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	3	0.7318
4-hydroxyphenylacetate 3-monooxygenase	Q8YHT7	Q8YHT7_BRUME	Brucella melitensis biotype 1	2	0.7314
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	2	0.7310
HTH-type transcriptional regulator QacR	P0A0N4	QACR_STAAU	Staphylococcus aureus	3	0.7303
Gag-Pol polyprotein	O12158	POL_HV192	Human immunodeficiency virus type 1 group M subtype C	3	0.7299
Chalcone--flavanone isomerase 1	P28012	CFI1_MEDSA	Medicago sativa	3	0.7288
Transcriptional regulator, PadR-like family	A2RI36	A2RI36_LACLM	Lactococcus lactis subsp. cremoris	2	0.7272
NAD-capped RNA hydrolase NudC	P32664	NUDC_ECOLI	Escherichia coli	3	0.7271
Transthyretin	Q9PTT3	Q9PTT3_SPAAU	Sparus aurata	3	0.7267
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	3	0.7262
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7242
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7240
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	Q8N5Z0	AADAT_HUMAN	Homo sapiens	2	0.7240
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7230
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7226
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7225
Succinate dehydrogenase flavoprotein subunit	P0AC41	SDHA_ECOLI	Escherichia coli	3	0.7215
Bifunctional epoxide hydrolase 2	P34913	HYES_HUMAN	Homo sapiens	2	0.7214
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7210
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.7201
Mitochondrial poly(A) polymerase	F1NBW0	F1NBW0_CHICK	Gallus gallus	2	0.7196
Casein kinase I isoform delta	P48730	KC1D_HUMAN	Homo sapiens	3	0.7179
Oxysterols receptor LXR-beta	P55055	NR1H2_HUMAN	Homo sapiens	3	0.7170
Large structural protein	Q91L20	Q91L20_9MONO	Human metapneumovirus	3	0.7162
Dihydrofolate reductase	Q81R22	Q81R22_BACAN	Bacillus anthracis	3	0.7153
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7133
Serine/threonine-protein kinase 24	Q9Y6E0	STK24_HUMAN	Homo sapiens	3	0.7129
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.7119
Chitinase A	Q9AMP1	Q9AMP1_VIBHA	Vibrio harveyi	3	0.7117
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	2	0.7116
Prostaglandin G/H synthase 1	P05979	PGH1_SHEEP	Ovis aries	3	0.7110
Glutathione S-transferase P	P09211	GSTP1_HUMAN	Homo sapiens	2	0.7109
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7104
Major strawberry allergen Fra a 1-3	D0E0C7	FRA13_FRAAN	Fragaria ananassa	3	0.7099
Dihydrofolate reductase	P00374	DYR_HUMAN	Homo sapiens	3	0.7097
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	P49354	FNTA_HUMAN	Homo sapiens	4	0.7087
Gag-Pol polyprotein	P05896	POL_SIVM1	Simian immunodeficiency virus	3	0.7072
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7070
Beta-secretase 1	P56817	BACE1_HUMAN	Homo sapiens	3	0.7060
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7056
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7050
Poly [ADP-ribose] polymerase tankyrase-2	Q9H2K2	TNKS2_HUMAN	Homo sapiens	4	0.7045
Chromosome-associated kinesin KIF4	P33174	KIF4_MOUSE	Mus musculus	2	0.7036
Serine/threonine-protein kinase pim-1	P11309	PIM1_HUMAN	Homo sapiens	3	0.7033
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7033
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1	O50008	METE1_ARATH	Arabidopsis thaliana	2	0.7025
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.7021
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7021
Glucan 1,3-beta-glucosidase	P29717	EXG1_CANAL	Candida albicans	3	0.7018
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.7016
Nuclear receptor subfamily 1 group I member 2	O75469	NR1I2_HUMAN	Homo sapiens	3	0.7012

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