(7R,14S)-trans-N-methylcanadinium nitrate - Compound Card

(7R,14S)-trans-N-methylcanadinium nitrate

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(7R,14S)-trans-N-methylcanadinium nitrate

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1c(OC)ccc2c1C[N+]1(C)CCc3c(C1C2)cc1c(c3)OCO1
InChI InChI=1S/C21H24NO4/c1-22-7-6-14-9-19-20(26-12-25-19)10-15(14)17(22)8-13-4-5-18(23-2)21(24-3)16(13)11-22/h4-5,9-10,17H,6-8,11-12H2,1-3H3/q+1
InChIKey IPABSWBNWMXCHM-UHFFFAOYSA-N
Formula C21H24NO4+
HBA 4
HBD 0
MW 354.43
Rotatable Bonds 2
TPSA 36.92
LogP 3.23
Number Rings 5
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 1
Fraction CSP3 0.43
Exact Mass 354.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Glaucium arabicum Papaveraceae Plantae 2072396

Showing of synonyms

  • Elbermawi A, Sallam A, et al. (2018). Bioactive isoquinoline alkaloids from Glaucium arabicum. Phytochemistry Letters, 2018, 28, 139-144. [View]
Pubchem: 156308
Bindingdb: 50206180

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)cc3c(c2)C4[NH+](CC3)Cc5c(C4)cccc5

Level: 0

Mol. Weight: 354.43 g/mol

Antimelanogenesis

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.15

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
41.59
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
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.290
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.870
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.130
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
8.810
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
-5.360
Rat (Acute)
2.720
Rat (Chronic Oral)
0.860
Fathead Minnow
4.890
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
420.010
Hydration Free Energy
-6.470
Log(D) at pH=7.4
2.390
Log(P)
-0.43
Log S
-0.76
Log(Vapor Pressure)
-8.42
Melting Point
200.54
pKa Acid
9.67
pKa Basic
4.14
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9504
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9369
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.9357
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9177
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9175
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9103
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.9103
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.9048
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8961
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8878
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8853
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8818
S-norcoclaurine synthase Q67A25 NCS_THLFG Thalictrum flavum subsp. glaucum 3 0.8692
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8681
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8643
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8622
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8579
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8508
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8503
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8502
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8470
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8461
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8447
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8420
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8399
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8394
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8356
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8355
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8347
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.8196
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.8190
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8130
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8094
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8052
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.8031
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7983
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7956
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7953
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7953
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7947
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7900
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7892
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7874
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7871
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7738
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7713
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7711
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7694
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7674
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7666
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7660
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.7659
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7653
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7631
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7623
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7606
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7586
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7582
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7547
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7539
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7502
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7486
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7485
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.7485
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7480
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7469
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 2 0.7464
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7457
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7453
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7436
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7433
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7427
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7413
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7412
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7408
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 2 0.7401
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7399
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7398
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 2 0.7395
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7390
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7384
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7380
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7376
Putative cytochrome P450 Q70AS3 Q70AS3_STRPE Streptomyces peucetius 3 0.7352
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7341
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7325
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 2 0.7311
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7310
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 3 0.7309
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7309
Secoisolariciresinol dehydrogenase Q94KL8 SILD_PODPE Podophyllum peltatum 3 0.7308
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7291
Ditrans,polycis-undecaprenyl-diphosphate synthase ((2E,6E)-farnesyl-diphosphate specific) P60472 UPPS_ECOLI Escherichia coli 2 0.7267
Beta-adrenergic receptor kinase 1 P25098 ARBK1_HUMAN Homo sapiens 3 0.7255
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 2 0.7253
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7241
Aldehyde dehydrogenase, mitochondrial P05091 ALDH2_HUMAN Homo sapiens 3 0.7235
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 2 0.7235
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7233
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7225
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7223
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7212
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7205
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7201
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7197
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7196
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7194
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7193
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7193
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7188
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7182
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7178
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7175
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7174
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7167
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7167
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7162
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7150
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7146
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 2 0.7145
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7143
Protein mono-ADP-ribosyltransferase PARP15 Q460N3 PAR15_HUMAN Homo sapiens 3 0.7139
Serine hydroxymethyltransferase Q7SIB6 Q7SIB6_GEOSE Geobacillus stearothermophilus 3 0.7137
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7134
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7127
Chitinase Q54276 Q54276_SERMA Serratia marcescens 2 0.7126
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7119
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7115
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7111
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7108
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7104
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7103
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7091
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7084
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7075
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7070
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7069
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7067
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7062
Poly [ADP-ribose] polymerase 1 P26446 PARP1_CHICK Gallus gallus 4 0.7058
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7050
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7040
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7038
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7038
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7033
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7030
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7017
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7007

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