Glaucine - Compound Card

Glaucine

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Glaucine

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1cc2c(cc1OC)C[C@H]1c3c2c(OC)c(OC)cc3CCN1C
InChI InChI=1S/C21H25NO4/c1-22-7-6-12-9-18(25-4)21(26-5)20-14-11-17(24-3)16(23-2)10-13(14)8-15(22)19(12)20/h9-11,15H,6-8H2,1-5H3/t15-/m0/s1
InChIKey RUZIUYOSRDWYQF-HNNXBMFYSA-N
Formula C21H25NO4
HBA 5
HBD 0
MW 355.43
Rotatable Bonds 4
TPSA 40.16
LogP 3.47
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.43
Exact Mass 355.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Glaucium flavum Papaveraceae Plantae 56853

Showing of synonyms

  • Bournine L, Bensalem S, et al. (2013). Identification and quantification of the main active anticancer alkaloids from the root of Glaucium flavum. International Journal of Molecular Sciences,2013,14(12),23533-23544. [View] [PubMed]
Pubchem: 16754
Kegg Ligand: C09446
Chebi: 5373
Nmrshiftdb2: 60030669
Metabolights: MTBLC5373
Pdb Ligand: 08V
Bindingdb: 50197829
CPRiL: 42350
Structure

SMILES: c1cccc(c1c23)CC4c2c(ccc3)CCN4

Level: 0

Mol. Weight: 355.43 g/mol

Anticancer

Absorption

Caco-2 (logPapp)
-4.94
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.86

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.830
Plasma Protein Binding
45.72
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
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
9.060
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
3.090
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.900
Liver Injury II
Safe
hERG Blockers
Toxic
Daphnia Maga
10.110
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
-7.050
Rat (Acute)
2.850
Rat (Chronic Oral)
1.680
Fathead Minnow
4.940
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
400.360
Hydration Free Energy
-8.180
Log(D) at pH=7.4
3.260
Log(P)
2.39
Log S
-2.71
Log(Vapor Pressure)
-7.49
Melting Point
147.77
pKa Acid
11.04
pKa Basic
8.75
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.9554
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.9554
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9384
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9384
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9347
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9347
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9321
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9321
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9299
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9299
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.9108
Cis-2,3-dihydrobiphenyl-2,3-diol dehydrogenase Q46381 BPHB_COMTE Comamonas testosteroni 3 0.9108
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8967
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8967
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8946
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 4 0.8946
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8589
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8589
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8550
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8550
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8516
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8516
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8488
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8488
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8488
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.8488
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8426
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8426
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8365
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8365
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8325
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8325
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8315
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8315
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8291
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.8291
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8269
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8269
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8244
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8244
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8193
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8193
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8071
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8071
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8062
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8062
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8028
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8028
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8021
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8021
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7980
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7980
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7963
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7963
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7951
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7951
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7870
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7870
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7863
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7863
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7840
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7840
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7678
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7678
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7655
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7655
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7629
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7629
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7627
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7627
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7616
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7616
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7613
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7613
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7580
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7580
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7540
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7540
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7529
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7529
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7479
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7479
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7475
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7475
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7454
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 3 0.7454
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7453
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7453
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7447
Fatty acid-binding protein, intestinal P12104 FABPI_HUMAN Homo sapiens 3 0.7447
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7442
Biphenyl-2,3-diol 1,2-dioxygenase P17297 BPHC_PSES1 Pseudomonas sp 3 0.7442
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7441
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7441
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7434
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7434
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7431
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7431
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7401
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7401
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7348
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7348
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7328
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 3 0.7328
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7316
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7316
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7304
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7304
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7304
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7304
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7297
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 4 0.7297
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7244
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7244
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7230
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7230
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7192
Serine/threonine-protein kinase Nek2 P51955 NEK2_HUMAN Homo sapiens 3 0.7192
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7188
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7188
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7178
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7178
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7176
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7176
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7173
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7173
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7153
L-methionine gamma-lyase Q84AR1 Q84AR1_CITFR Citrobacter freundii 3 0.7153
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7147
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7147
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7145
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7145
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7144
Calmodulin-1 P0DP29 CALM1_RAT Rattus norvegicus 3 0.7144
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7124
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 3 0.7124
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7110
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7110
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7101
Focal adhesion kinase 1 Q00944 FAK1_CHICK Gallus gallus 3 0.7101
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7082
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7082
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7079
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7079
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7075
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.7075
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7072
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7072
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7066
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7066
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7052
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7052
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7049
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7049
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7041
Dihydroflavonol 4-reductase P51110 DFRA_VITVI Vitis vinifera 3 0.7041
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7029
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7029
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7023
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7023
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7018
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7018
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7014
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.7014
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7008
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7008

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