Isocorydine - Compound Card

Isocorydine

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Isocorydine

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1ccc2c(c1O)c1c(OC)c(OC)cc3c1[C@H](C2)N(C)CC3
InChI InChI=1S/C20H23NO4/c1-21-8-7-12-10-15(24-3)20(25-4)18-16(12)13(21)9-11-5-6-14(23-2)19(22)17(11)18/h5-6,10,13,22H,7-9H2,1-4H3/t13-/m0/s1
InChIKey QELDJEKNFOQJOY-ZDUSSCGKSA-N
Formula C20H23NO4
HBA 5
HBD 1
MW 341.41
Rotatable Bonds 3
TPSA 51.16
LogP 3.17
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 341.16
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hypecoum procumbens Hypecoaceae Plantae 391933
2 Glaucium corniculatum Papaveraceae Plantae 1533087

Showing of synonyms

  • Saad HEA (1995). (±)-8-oxohypecorinine from Hypecoum procumbens Var. Glaucescens. Phytochemistry,1995,38(4),1049-1051. [View]
  • Al-Wakeel SAM, Moubasher MH, et al. (1995). Alkaloids from Glaucium corniculatum (L.) of Egyptian origin. Biochemical Systematics and Ecology,1995,23(3),337-338. [View]
Pubchem: 10143
Kegg Ligand: C09549
Chebi: 6000
Nmrshiftdb2: 60026209
Metabolights: MTBLC6000
Bindingdb: 50250273
CPRiL: 90426
Structure

SMILES: c1cccc(c1c23)CC4c2c(ccc3)CCN4

Level: 0

Mol. Weight: 341.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.83
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.810
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.900
Plasma Protein Binding
53.91
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
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
12.060
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
2.900
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.530
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
9.480
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
-4.370
Rat (Acute)
2.580
Rat (Chronic Oral)
1.920
Fathead Minnow
4.770
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
402.610
Hydration Free Energy
-8.630
Log(D) at pH=7.4
2.940
Log(P)
1.98
Log S
-2.48
Log(Vapor Pressure)
-7.6
Melting Point
171.61
pKa Acid
9.51
pKa Basic
8.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9398
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9398
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9363
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9363
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9351
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9351
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8560
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8560
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8558
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8558
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8546
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8546
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8509
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8509
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8506
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8506
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8432
Renin P00797 RENI_HUMAN Homo sapiens 3 0.8432
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8389
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8389
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8309
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8309
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8295
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8295
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8199
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8199
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8159
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8159
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8116
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8116
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7999
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7999
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7988
Glycylpeptide N-tetradecanoyltransferase Q4Q5S8 Q4Q5S8_LEIMA Leishmania major 3 0.7988
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7963
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7963
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7905
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7905
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7846
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7846
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7794
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7794
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7765
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7765
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7581
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7581
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7569
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7569
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7564
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7564
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7546
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7546
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7540
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7540
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7513
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7513
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7399
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7399
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7397
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7397
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7341
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7341
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7335
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7335
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7293
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7293
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7282
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7282
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7277
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7277
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7266
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7266
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7263
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7263
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7259
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7259
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7246
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7246
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7240
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7240
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7229
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7229
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7226
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7226
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7223
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7223
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7209
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7209
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7166
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7166
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase P23970 MEND_BACSU Bacillus subtilis 3 0.7128
2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase P23970 MEND_BACSU Bacillus subtilis 3 0.7128
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7124
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7124
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7123
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7123
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7117
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7117
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7069
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7069
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7065
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.7065
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7032
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7032
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7017
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7017
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7011
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7011
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7007
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7007

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