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Isocorydine N-oxide
- Family: Plantae - Papaveraceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Isoquinoline Alkaloid
| Canonical Smiles | COc1ccc2c(c1O)c1c(OC)c(OC)cc3c1[C@H](C2)N(=O)(C)CC3 |
|---|---|
| InChI | InChI=1S/C20H23NO5/c1-21(23)8-7-12-10-15(25-3)20(26-4)18-16(12)13(21)9-11-5-6-14(24-2)19(22)17(11)18/h5-6,10,13,22H,7-9H2,1-4H3/t13-,21?/m0/s1 |
| InChIKey | AGIAQPIYGHUVMY-JRTLGTJJSA-N |
| Formula | C20H23NO5 |
| HBA | 5 |
| HBD | 1 |
| MW | 357.41 |
| Rotatable Bonds | 3 |
| TPSA | 70.98 |
| LogP | 3.18 |
| Number Rings | 4 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.4 |
| Exact Mass | 357.16 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Glaucium corniculatum | Papaveraceae | Plantae | 1533087 |
Showing of synonyms
Isocorydine N-oxide
UNII-45U4MW62MJ
25405-80-5
45U4MW62MJ
(+)-ISOCORYDINE N-OXIDE
DTXSID30180066
ISOCORYDINE N-OXIDE, (+)-
4H-DIBENZO(DE,G)QUINOLIN-11-OL, 5,6,6A,7-TETRAHYDRO-1,2,10-TRIMETHOXY-6-METHYL-, 6-OXIDE, (6AS)-
DTXCID40102557
6Aalpha-APORPHIN-11-OL, 1,2,10-TRIMETHOXY-, 6-OXIDE
(6aS)-1,2,10-trimethoxy-6-methyl-6-oxido-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinolin-6-ium-11-ol
Q27258862
6A.ALPHA.-APORPHIN-11-OL, 1,2,10-TRIMETHOXY-, 6-OXIDE
- 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:
71587071
Cas:
25405-80-5
Zinc:
ZINC000014559004
Nmrshiftdb2:
60145470
Comptox:
DTXSID30180066
No compound-protein relationship available.
SMILES: c1cccc(c1c23)CC4c2c(ccc3)CC[N+]4=O
Level: 0
Mol. Weight: 357.41 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.14
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.820
- Human Oral Bioavailability 50%
- Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.28
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.600
- Plasma Protein Binding
- 80.14
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Inhibitor
- CYP 1A2 Substrate
- Non-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
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.200
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 3.550
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.490
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.920
- 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
- -0.780
- Rat (Acute)
- 2.490
- Rat (Chronic Oral)
- 1.750
- Fathead Minnow
- 4.660
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Toxic
- SR-ARE
- Toxic
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 422.390
- Hydration Free Energy
- -7.540
- Log(D) at pH=7.4
- 1.450
- Log(P)
- 0.73
- Log S
- -1.42
- Log(Vapor Pressure)
- -8.55
- Melting Point
- 225.68
- pKa Acid
- 7.14
- pKa Basic
- 1.66
| 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 | 0.9409 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.9409 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9373 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.9373 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9346 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.9346 |
| Three-prime repair exonuclease 1 | Q91XB0 | TREX1_MOUSE | Mus musculus | 3 | 0.8773 |
| Three-prime repair exonuclease 1 | Q91XB0 | TREX1_MOUSE | Mus musculus | 3 | 0.8773 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 4 | 0.8771 |
| NAD(P)H dehydrogenase [quinone] 1 | P15559 | NQO1_HUMAN | Homo sapiens | 4 | 0.8771 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.8637 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 4 | 0.8637 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8425 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.8425 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.8374 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.8374 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8303 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8303 |
| Cysteine desulfurase IscS 2 | O29689 | ISCS2_ARCFU | Archaeoglobus fulgidus | 3 | 0.8278 |
| Cysteine desulfurase IscS 2 | O29689 | ISCS2_ARCFU | Archaeoglobus fulgidus | 3 | 0.8278 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8069 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.8069 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7888 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7888 |
| Cysteine desulfurase IscS 2 | O29689 | ISCS2_ARCFU | Archaeoglobus fulgidus | 3 | 0.7874 |
| Cysteine desulfurase IscS 2 | O29689 | ISCS2_ARCFU | Archaeoglobus fulgidus | 3 | 0.7874 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 3 | 0.7863 |
| NmrA-like family domain-containing protein 1 | Q9HBL8 | NMRL1_HUMAN | Homo sapiens | 3 | 0.7863 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7838 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7838 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7833 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7833 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7821 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7821 |
| Glycylpeptide N-tetradecanoyltransferase | Q4Q5S8 | Q4Q5S8_LEIMA | Leishmania major | 3 | 0.7801 |
| Glycylpeptide N-tetradecanoyltransferase | Q4Q5S8 | Q4Q5S8_LEIMA | Leishmania major | 3 | 0.7801 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 3 | 0.7768 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 3 | 0.7768 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.7691 |
| Renin | P00797 | RENI_HUMAN | Homo sapiens | 3 | 0.7691 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 4 | 0.7664 |
| 3',5'-cyclic-AMP phosphodiesterase 4B | Q07343 | PDE4B_HUMAN | Homo sapiens | 4 | 0.7664 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7654 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7654 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7644 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7644 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7616 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 3 | 0.7616 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7607 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7607 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7570 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 3 | 0.7570 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7428 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7428 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7424 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 2 | 0.7424 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7313 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.7313 |
| 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 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7266 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7266 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 3 | 0.7257 |
| Phenazine biosynthesis protein A/B | Q396C9 | Q396C9_BURL3 | Burkholderia lata | 3 | 0.7257 |
| Benzoylformate decarboxylase | P20906 | MDLC_PSEPU | Pseudomonas putida | 3 | 0.7250 |
| Benzoylformate decarboxylase | P20906 | MDLC_PSEPU | Pseudomonas putida | 3 | 0.7250 |
| Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7249 |
| Stimulator of interferon genes protein | Q86WV6 | STING_HUMAN | Homo sapiens | 3 | 0.7249 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7225 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7225 |
| Fatty acid-binding protein, adipocyte | P15090 | FABP4_HUMAN | Homo sapiens | 3 | 0.7139 |
| Fatty acid-binding protein, adipocyte | P15090 | FABP4_HUMAN | Homo sapiens | 3 | 0.7139 |
| ATP-dependent helicase/nuclease subunit A | P23478 | ADDA_BACSU | Bacillus subtilis | 2 | 0.7136 |
| ATP-dependent helicase/nuclease subunit A | P23478 | ADDA_BACSU | Bacillus subtilis | 2 | 0.7136 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7132 |
| Riboflavin synthase | P0AFU8 | RISA_ECOLI | Escherichia coli | 3 | 0.7132 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7130 |
| cGMP-specific 3',5'-cyclic phosphodiesterase | O76074 | PDE5A_HUMAN | Homo sapiens | 3 | 0.7130 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7118 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7118 |
| Benzaldehyde lyase | Q9F4L3 | Q9F4L3_PSEFL | Pseudomonas fluorescens | 3 | 0.7080 |
| Benzaldehyde lyase | Q9F4L3 | Q9F4L3_PSEFL | Pseudomonas fluorescens | 3 | 0.7080 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7063 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 3 | 0.7063 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7041 |
| Focal adhesion kinase 1 | Q00944 | FAK1_CHICK | Gallus gallus | 3 | 0.7041 |