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1-methyl-2-acetyl-6-acetoxy-7‐methoxy-1,2,3,4-tetrahydroisoquinoline

Family: Plantae - Chenopodiaceae
Kingdom: Plantae
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid

Canonical Smiles	COc1cc2c(cc1OC(=O)C)CCN(C2C)C(=O)C
InChI	InChI=1S/C15H19NO4/c1-9-13-8-14(19-4)15(20-11(3)18)7-12(13)5-6-16(9)10(2)17/h7-9H,5-6H2,1-4H3
InChIKey	SJYNSJDWNLLVMJ-UHFFFAOYSA-N
Formula	C₁₅H₁₉NO₄
HBA	4
HBD	0
MW	277.32
Rotatable Bonds	2
TPSA	55.84
LogP	2.09
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	20
Formal Charge	0
Fraction CSP3	0.47
Exact Mass	277.13
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Haloxylon scoparium	Chenopodiaceae	Plantae	1665493

Showing of synonyms

Lachkar N, Lamchouri F, et al. (2021). Chemical composition, phenolic content and antioxidant capacity of Haloxylon scoparium extracts. Evidence-based complementary and alternative medicine : eCAM, 2021, 2021, 9011168. [View] [PubMed]

Pubchem: 613235

No compound-protein relationship available.

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 277.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -4.55
Human Oral Bioavailability 20%: Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -4.270
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -2.53

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Penetrable
Fraction Unbound (Human): 0.510
Plasma Protein Binding: 23.59
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: Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 7.880
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: 0.850
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 1.190
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 4.220
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: 2.750
Rat (Acute): 2.220
Rat (Chronic Oral): 1.740
Fathead Minnow: 4.140
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: 348.690
Hydration Free Energy: -8.620
Log(D) at pH=7.4: 1.330
Log(P): 1.41
Log S: -1.83
Log(Vapor Pressure): -5.35
Melting Point: 100.02
pKa Acid: 10.99
pKa Basic: 6.13

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	0.9490
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9464
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.9435
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.9268
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial	Q0QF01	SDHA_PIG	Sus scrofa	3	0.9157
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	3	0.9100
Retinoic acid receptor RXR-alpha	P19793	RXRA_HUMAN	Homo sapiens	3	0.9063
Casein kinase II subunit alpha'	P19784	CSK22_HUMAN	Homo sapiens	3	0.9032
3',5'-cyclic-AMP phosphodiesterase 4D	Q08499	PDE4D_HUMAN	Homo sapiens	3	0.8914
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A	Q9Y233	PDE10_HUMAN	Homo sapiens	3	0.8873
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.8729
Pentaerythritol tetranitrate reductase	P71278	P71278_ENTCL	Enterobacter cloacae	3	0.8710
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	3	0.8697
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.8691
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8616
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	3	0.8579
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.8515
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.8458
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8366
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.8328
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.8314
3-alpha-hydroxysteroid dehydrogenase	P23457	DIDH_RAT	Rattus norvegicus	3	0.8313
Sulfotransferase 2A1	Q06520	ST2A1_HUMAN	Homo sapiens	3	0.8231
2-phospho-L-lactate transferase	Q8PVT6	COFD_METMA	Methanosarcina mazei	3	0.8180
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8177
Acetylcholine-binding protein	P58154	ACHP_LYMST	Lymnaea stagnalis	3	0.8153
Sex hormone-binding globulin	P04278	SHBG_HUMAN	Homo sapiens	3	0.8150
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8137
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	3	0.8090
AGAP003309-PA	A0A1U7F4W2	A0A1U7F4W2_ANOGA	Anopheles gambiae	3	0.8080
Na(+):neurotransmitter symporter (Snf family)	O67854	O67854_AQUAE	Aquifex aeolicus	3	0.8076
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.8050
cGMP-specific 3',5'-cyclic phosphodiesterase	O76074	PDE5A_HUMAN	Homo sapiens	3	0.7913
cGMP-dependent protein kinase 1	P00516	KGP1_BOVIN	Bos taurus	3	0.7830
Cytochrome P450 monooxygenase	Q5YNS8	Q5YNS8_NOCFA	Nocardia farcinica	3	0.7816
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7806
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	3	0.7769
Phytohormone-binding protein	G7J032	PHBP_MEDTR	Medicago truncatula	4	0.7730
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7694
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7692
Sulfotransferase 2B1	O00204	ST2B1_HUMAN	Homo sapiens	2	0.7686
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7668
Corticosteroid-binding globulin	P08185	CBG_HUMAN	Homo sapiens	3	0.7629
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	2	0.7601
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7598
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7585
Lactoylglutathione lyase	Q9CPU0	LGUL_MOUSE	Mus musculus	2	0.7528
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7517
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7511
Genome polyprotein	P26663	POLG_HCVBK	Hepatitis C virus genotype 1b	3	0.7507
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7497
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7494
17-beta-hydroxysteroid dehydrogenase type 1	P14061	DHB1_HUMAN	Homo sapiens	2	0.7468
Dihydroorotate dehydrogenase (quinone), mitochondrial	Q02127	PYRD_HUMAN	Homo sapiens	3	0.7460
NADPH dehydrogenase 1	Q02899	OYE1_SACPS	Saccharomyces pastorianus	2	0.7460
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform	P48736	PK3CG_HUMAN	Homo sapiens	3	0.7439
Steroid Delta-isomerase	P07445	SDIS_PSEPU	Pseudomonas putida	2	0.7438
Ferrochelatase, mitochondrial	P22830	HEMH_HUMAN	Homo sapiens	2	0.7410
Tetracycline repressor protein class H	P51561	TETR8_PASMD	Pasteurella multocida	2	0.7409
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	2	0.7402
Type IV / VI secretion system DotU domain-containing protein	Q9KN50	Q9KN50_VIBCH	Vibrio cholerae serotype O1	2	0.7393
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	3	0.7391
Bromodomain adjacent to zinc finger domain protein 2B	Q9UIF8	BAZ2B_HUMAN	Homo sapiens	2	0.7366
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7362
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7362
3'-5' exoribonuclease Rv2179c	P9WJ73	EXRBN_MYCTU	Mycobacterium tuberculosis	2	0.7346
Pheromone-binding protein ASP1	Q9U9J6	Q9U9J6_APIME	Apis mellifera	2	0.7341
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7308
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7303
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	3	0.7298
Methylketone synthase I	E0YCS2	E0YCS2_SOLHA	Solanum habrochaites	2	0.7284
Acetylcholinesterase	P22303	ACES_HUMAN	Homo sapiens	3	0.7270
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7258
Metallo-beta-lactamase type 2	C7C422	BLAN1_KLEPN	Klebsiella pneumoniae	2	0.7257
Nuclear receptor subfamily 1 group I member 3	O35627	NR1I3_MOUSE	Mus musculus	2	0.7255
Polymerase acidic protein	C3W5S0	C3W5S0_I09A0	Influenza A virus	2	0.7255
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7252
RNA-dependent RNA polymerase	Q6A562	Q6A562_9VIRU	Thosea asigna virus	2	0.7236
Steroid Delta-isomerase	P00947	SDIS_COMTE	Comamonas testosteroni	2	0.7225
ADP-ribosylation factor 1	P84077	ARF1_HUMAN	Homo sapiens	2	0.7219
Aldo-keto reductase family 1 member C1	Q04828	AK1C1_HUMAN	Homo sapiens	2	0.7214
CmeR	Q7B8P6	Q7B8P6_CAMJU	Campylobacter jejuni	2	0.7213
Carminomycin 4-O-methyltransferase DnrK	Q06528	DNRK_STRPE	Streptomyces peucetius	2	0.7211
Prostaglandin reductase 2	Q8N8N7	PTGR2_HUMAN	Homo sapiens	2	0.7196
Aromatase	P11511	CP19A_HUMAN	Homo sapiens	3	0.7181
Beta-galactoside-specific lectin 4	Q6ITZ3	ML4_VISAL	Viscum album	2	0.7132
Mineralocorticoid receptor	P08235	MCR_HUMAN	Homo sapiens	3	0.7128
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7121
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7118
CCA-adding enzyme	O28126	CCA_ARCFU	Archaeoglobus fulgidus	2	0.7099
Pteridine reductase, putative	Q581W1	Q581W1_TRYB2	Trypanosoma brucei brucei	2	0.7098
3-phosphoinositide-dependent protein kinase 1	O15530	PDPK1_HUMAN	Homo sapiens	3	0.7092
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	3	0.7076
Fatty acid-binding protein, liver	P80226	FABPL_CHICK	Gallus gallus	2	0.7069
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta	P78356	PI42B_HUMAN	Homo sapiens	3	0.7063
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7057
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	2	0.7057
Acetylcholinesterase	P04058	ACES_TETCF	Tetronarce californica	3	0.7043
Dihydropteroate synthase	Q81VW8	Q81VW8_BACAN	Bacillus anthracis	3	0.7041
Adenylate cyclase type 5	P30803	ADCY5_CANLF	Canis lupus familiaris	3	0.7039
Thymidine kinase	P0DTH5	KITH_HHV11	Human herpesvirus 1	2	0.7036
Androgen receptor	P10275	ANDR_HUMAN	Homo sapiens	2	0.7018
Oxygenase	Q194P4	Q194P4_STRAA	Streptomyces argillaceus	3	0.7011
Aldo-keto reductase family 1 member C2	P52895	AK1C2_HUMAN	Homo sapiens	2	0.7011

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