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9-O-demethylhomolycorine
- Family: Amaryllidaceae
- Kingdom: Plantae
-
Class: Alkaloid
- Subclass: Amaryllidaceae Alkaloid
| Canonical Smiles | COc1cc2[C@@H]3[C@@H](CC=C4[C@H]3N(C)CC4)OC(=O)c2cc1O |
|---|---|
| InChI | InChI=1S/C17H19NO4/c1-18-6-5-9-3-4-13-15(16(9)18)10-8-14(21-2)12(19)7-11(10)17(20)22-13/h3,7-8,13,15-16,19H,4-6H2,1-2H3/t13-,15-,16-/m1/s1 |
| InChIKey | VLDOBKJPRUQEEC-FVQBIDKESA-N |
| Formula | C17H19NO4 |
| HBA | 5 |
| HBD | 1 |
| MW | 301.34 |
| Rotatable Bonds | 1 |
| TPSA | 59.0 |
| LogP | 2.06 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 22 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.47 |
| Exact Mass | 301.13 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Narcissus tazetta | Amaryllidaceae | Plantae | 54860 |
| 2 | Narcissus species | Amaryllidaceae | Plantae | 54843 |
Showing of synonyms
9-O-demethylhomolycorine
6879-81-8
CHEBI:31154
(5aR,11bS,11cS)-9-hydroxy-10-methoxy-1-methyl-2,3,5,5a,11b,11c-hexahydroisochromeno[3,4-g]indol-7-one
Lycorenan-7-one, 9-hydroxy-10-methoxy-1-methyl-
9-hydroxy-10-methoxy-1-methyllycorenan-7-one
C12190
CHEMBL1979251
DTXSID90988500
NSC683872
NSC-683872
NCI60_030153
Q27114182
- Evidente A, Lametta R, et al. (1994). 9-O-Demethylhomolycorine from Egyptian Narcissus tazetta. Archiv der Pharmazie,1994,327,595-596. [View]
- Shawky E, Abou-Donia AH, et al. (2015). HPTLC and GC/MS study of Amaryllidaceae alkaloids of two Narcissus species. Chemistry and Biodiversity,2015,12(8),1184-1199. [View] [PubMed]
Pubchem:
388787
Cas:
6879-81-8
Zinc:
ZINC000004102398
Kegg Ligand:
C12190
Chebi:
31154
Nmrshiftdb2:
60027252
Metabolights:
MTBLC31154
Chembl:
CHEMBL1979251
No compound-protein relationship available.
SMILES: C1CNC(C1=2)C3c4c(cccc4)C(=O)OC3CC2
Level: 0
Mol. Weight: 241.29 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -4.9
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -4.740
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.92
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Penetrable
- Fraction Unbound (Human)
- 0.460
- Plasma Protein Binding
- 35.59
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Substrate
- CYP 2C19 Inhibitor
- Inhibitor
- CYP 2C19 Substrate
- Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Substrate
- CYP 2D6 Inhibitor
- Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 16.970
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- 1.870
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- -0.640
- Liver Injury II
- Toxic
- hERG Blockers
- Toxic
- Daphnia Maga
- 9.450
- 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
- -2.700
- Rat (Acute)
- 2.650
- Rat (Chronic Oral)
- 1.850
- Fathead Minnow
- 4.020
- 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
- 377.330
- Hydration Free Energy
- -9.780
- Log(D) at pH=7.4
- 2.040
- Log(P)
- 1.78
- Log S
- -2.04
- Log(Vapor Pressure)
- -7.35
- Melting Point
- 189.67
- pKa Acid
- 7.74
- pKa Basic
- 8.06
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.9307 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.9307 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8812 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8812 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8771 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.8771 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8719 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8719 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8681 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8681 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8468 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8468 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8449 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.8449 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8438 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8438 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8272 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.8272 |
| tRNA (guanine-N(1)-)-methyltransferase | Q2GIL5 | TRMD_ANAPZ | Anaplasma phagocytophilum | 4 | 0.8181 |
| tRNA (guanine-N(1)-)-methyltransferase | Q2GIL5 | TRMD_ANAPZ | Anaplasma phagocytophilum | 4 | 0.8181 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 4 | 0.8090 |
| Ribosomal RNA small subunit methyltransferase Nep1 | Q57977 | NEP1_METJA | Methanocaldococcus jannaschii | 4 | 0.8090 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.8086 |
| Na(+):neurotransmitter symporter (Snf family) | O67854 | O67854_AQUAE | Aquifex aeolicus | 3 | 0.8086 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8080 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8080 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8045 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.8045 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7814 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7814 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7655 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7655 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7640 |
| Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial | Q0QF01 | SDHA_PIG | Sus scrofa | 3 | 0.7640 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7592 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7592 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7533 |
| Estrogen receptor | P03372 | ESR1_HUMAN | Homo sapiens | 3 | 0.7533 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7506 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7506 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 4 | 0.7504 |
| Deoxycytidine kinase | P27707 | DCK_HUMAN | Homo sapiens | 4 | 0.7504 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7458 |
| Pheromone-binding protein ASP1 | Q9U9J6 | Q9U9J6_APIME | Apis mellifera | 3 | 0.7458 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7402 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.7402 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7374 |
| Soluble cytochrome b562 | P0ABE7 | C562_ECOLX | Escherichia coli | 3 | 0.7374 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7359 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7359 |
| Diphthine synthase | O58456 | DPHB_PYRHO | Pyrococcus horikoshii | 4 | 0.7327 |
| Diphthine synthase | O58456 | DPHB_PYRHO | Pyrococcus horikoshii | 4 | 0.7327 |
| Mitogen-activated protein kinase 1 | P63086 | MK01_RAT | Rattus norvegicus | 3 | 0.7326 |
| Mitogen-activated protein kinase 1 | P63086 | MK01_RAT | Rattus norvegicus | 3 | 0.7326 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7259 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7259 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7254 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7254 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7237 |
| Laminarinase | Q9WXN1 | Q9WXN1_THEMA | Thermotoga maritima | 3 | 0.7237 |
| NAD-dependent protein deacetylase sirtuin-3, mitochondrial | Q9NTG7 | SIR3_HUMAN | Homo sapiens | 4 | 0.7234 |
| NAD-dependent protein deacetylase sirtuin-3, mitochondrial | Q9NTG7 | SIR3_HUMAN | Homo sapiens | 4 | 0.7234 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 3 | 0.7230 |
| 17-beta-hydroxysteroid dehydrogenase 14 | Q9BPX1 | DHB14_HUMAN | Homo sapiens | 3 | 0.7230 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7228 |
| Steroid Delta-isomerase | P00947 | SDIS_COMTE | Comamonas testosteroni | 3 | 0.7228 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7179 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7179 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7141 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7141 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7137 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7137 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7135 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7135 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7092 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7092 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7072 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7072 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7068 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7068 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7065 |
| Hypoxanthine-guanine phosphoribosyltransferase | P00492 | HPRT_HUMAN | Homo sapiens | 3 | 0.7065 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7065 |
| Lethal(3)malignant brain tumor-like protein 1 | Q9Y468 | LMBL1_HUMAN | Homo sapiens | 3 | 0.7065 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7057 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7057 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7051 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7051 |
| Riboflavin synthase | Q58584 | RISC_METJA | Methanocaldococcus jannaschii | 4 | 0.7050 |
| Riboflavin synthase | Q58584 | RISC_METJA | Methanocaldococcus jannaschii | 4 | 0.7050 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7032 |
| dTDP-4-dehydrorhamnose 3,5-epimerase | A0A6L7H6N0 | A0A1S0QLH9_BACAN | Bacillus anthracis | 3 | 0.7032 |