9-O-demethylhomolycorine - Compound Card

9-O-demethylhomolycorine

Select a section from the left sidebar

9-O-demethylhomolycorine

Structure
Zoomed Structure
  • Family: Plantae - 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

  • 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
Kegg Ligand: C12190
Chebi: 31154
Nmrshiftdb2: 60027252
Metabolights: MTBLC31154

No compound-protein relationship available.

Structure

SMILES: C1CNC(C1=2)C3c4c(cccc4)C(=O)OC3CC2

Level: 0

Mol. Weight: 301.34 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

Download SDF