2-acetyl-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diyl diacetate - Compound Card

2-acetyl-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diyl diacetate

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2-acetyl-1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diyl diacetate

Structure
Zoomed Structure
  • Family: Plantae - Chenopodiaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles CC(=O)Oc1cc2c(cc1OC(=O)C)CCN(C2C)C(=O)C
InChI InChI=1S/C16H19NO5/c1-9-14-8-16(22-12(4)20)15(21-11(3)19)7-13(14)5-6-17(9)10(2)18/h7-9H,5-6H2,1-4H3
InChIKey DFABDZJGJOKSBM-UHFFFAOYSA-N
Formula C16H19NO5
HBA 5
HBD 0
MW 305.33
Rotatable Bonds 2
TPSA 72.91
LogP 2.0
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 305.13
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]

No compound-protein relationship available.

Structure

SMILES: C1CNCc(c12)cccc2

Level: 0

Mol. Weight: 305.33 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.5
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.49
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.59

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.47
Plasma Protein Binding
18.6
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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
9.06
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.66
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.38
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.56
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
2.5
Rat (Acute)
2.12
Rat (Chronic Oral)
1.92
Fathead Minnow
4.2
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
366.95
Hydration Free Energy
-8.33
Log(D) at pH=7.4
1.08
Log(P)
1.41
Log S
-2.56
Log(Vapor Pressure)
-5.86
Melting Point
119.35
pKa Acid
10.13
pKa Basic
6.34
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 0.9596
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9279
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9199
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9191
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9106
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.9090
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.9023
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8584
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8354
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8343
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8304
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8297
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8253
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8244
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 3 0.8182
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8130
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7976
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7969
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7966
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7887
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7880
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7701
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7676
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7596
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7563
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7527
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7525
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7518
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7504
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7497
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.7497
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7426
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7425
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7423
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7410
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7396
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7374
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7355
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7315
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7302
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7285
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7265
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7262
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7261
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7252
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 2 0.7247
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7245
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7243
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7242
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7240
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7225
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7214
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7211
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7210
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7200
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7186
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7182
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7176
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7172
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7163
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7156
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7143
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7134
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7124
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7119
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7112
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7101
Dihydroorotate dehydrogenase (quinone), mitochondrial Q02127 PYRD_HUMAN Homo sapiens 3 0.7095
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7091
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7086
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7074
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7070
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 2 0.7066
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7063
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7048
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7047
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7025
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7009
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7001

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