Araglaucine A - Compound Card

Araglaucine A

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Araglaucine A

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COC(=O)c1c2OCOc2ccc1C(=O)c1nccc2c1cc1OCOc1c2
InChI InChI=1S/C20H13NO7/c1-24-20(23)16-11(2-3-13-19(16)28-9-25-13)18(22)17-12-7-15-14(26-8-27-15)6-10(12)4-5-21-17/h2-7H,8-9H2,1H3
InChIKey ZHIOBQMWWICIRQ-UHFFFAOYSA-N
Formula C20H13NO7
HBA 8
HBD 0
MW 379.32
Rotatable Bonds 3
TPSA 93.18
LogP 2.71
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.15
Exact Mass 379.07
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Glaucium arabicum Papaveraceae Plantae 2072396

Showing of synonyms

  • Elbermawi A, Sallam A, et al. (2018). Bioactive isoquinoline alkaloids from Glaucium arabicum. Phytochemistry Letters, 2018, 28, 139-144. [View]

No compound-protein relationship available.

Structure

SMILES: O1COc(c12)ccc(c2)C(=O)c(ncc3)c(c4)c3cc(c45)OCO5

Level: 1

Mol. Weight: 379.32 g/mol

Structure

SMILES: O1COc(c12)cc3c(c2)ccnc3

Level: 0

Mol. Weight: 379.32 g/mol

Structure

SMILES: O1COc(c12)cccc2

Level: 0

Mol. Weight: 379.32 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.520
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.450
Plasma Protein Binding
78.58
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.220
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.590
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.020
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.170
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
-27.020
Rat (Acute)
2.790
Rat (Chronic Oral)
2.100
Fathead Minnow
5.540
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
469.870
Hydration Free Energy
-5.950
Log(D) at pH=7.4
3.370
Log(P)
3.21
Log S
-5.18
Log(Vapor Pressure)
-9.0
Melting Point
185.05
pKa Acid
7.69
pKa Basic
-0.17
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.9751
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.9587
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.9312
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.9311
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.9215
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9177
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8845
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8717
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.8665
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8660
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8598
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8549
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8427
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8398
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.8343
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8298
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8281
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.8273
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8236
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8208
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8198
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8194
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8122
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8093
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8026
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8012
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7997
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7995
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7965
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.7953
11-beta-hydroxysteroid dehydrogenase 1 Q6QLL4 DHI1_CAVPO Cavia porcellus 3 0.7902
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7872
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7870
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7859
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7847
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7846
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7813
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7780
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7772
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7753
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7728
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7708
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7708
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7665
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7623
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7619
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7603
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7590
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7576
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7570
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7556
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7553
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7526
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7510
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7507
Actin-related protein 3 P61157 ARP3_BOVIN Bos taurus 4 0.7487
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7485
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7479
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7476
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7458
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 3 0.7457
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7451
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7443
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7419
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7419
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7418
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7409
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7403
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7397
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7391
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7388
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7386
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7386
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7378
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7373
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7356
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7353
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7350
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7348
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7344
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7342
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7332
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7310
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7296
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7294
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7285
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7278
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7275
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7270
Carbonic anhydrase 4 P22748 CAH4_HUMAN Homo sapiens 3 0.7260
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7251
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7244
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7238
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7230
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7227
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7223
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7210
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7207
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7197
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7193
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7183
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7178
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7172
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7157
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7150
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7135
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7133
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7130
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7125
Isoflavone-7-O-methyltransferase 8 O24529 7OMT8_MEDSA Medicago sativa 4 0.7116
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7097
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7085
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7083
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7082
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7073
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7067
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.7067
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7063
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7060
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7059
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7052
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7048
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7048
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7044
Rifampin ADP-ribosyl transferase A0QRS5 A0QRS5_MYCS2 Mycolicibacterium smegmatis155) 3 0.7043
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7041
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7036
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7028
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7025
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7022
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7010
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7007
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7004
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7001

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