Araglaucine B - Compound Card

Araglaucine B

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Araglaucine B

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles COc1c(OC)ccc2c1C(=O)NC2(O)c1nccc2c1cc1OCOc1c2
InChI InChI=1S/C20H16N2O6/c1-25-13-4-3-12-16(17(13)26-2)19(23)22-20(12,24)18-11-8-15-14(27-9-28-15)7-10(11)5-6-21-18/h3-8,24H,9H2,1-2H3,(H,22,23)
InChIKey SPVGQUOEZLKSQZ-UHFFFAOYSA-N
Formula C20H16N2O6
HBA 7
HBD 2
MW 380.36
Rotatable Bonds 3
TPSA 99.14
LogP 1.92
Number Rings 5
Number Aromatic Rings 3
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.2
Exact Mass 380.1
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: c1cccc(c12)C(NC2=O)c(ncc3)c(c4)c3cc(c45)OCO5

Level: 1

Mol. Weight: 380.36 g/mol

Structure

SMILES: O1COc(c12)cc3c(c2)ccnc3

Level: 0

Mol. Weight: 380.36 g/mol

Structure

SMILES: O=C1NCc(c12)cccc2

Level: 0

Mol. Weight: 380.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.720
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.540
Plasma Protein Binding
76.31
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.090
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.100
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
Safe
Daphnia Maga
5.700
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
Toxic
T. Pyriformis
-22.460
Rat (Acute)
2.170
Rat (Chronic Oral)
2.250
Fathead Minnow
4.970
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
465.460
Hydration Free Energy
-6.680
Log(D) at pH=7.4
1.670
Log(P)
1.55
Log S
-3.74
Log(Vapor Pressure)
-9.22
Melting Point
204.92
pKa Acid
8.67
pKa Basic
2.23
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8962
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8923
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8776
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8412
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8400
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8372
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8354
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8255
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8150
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8118
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.8091
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8051
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7959
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7956
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7926
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.7871
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7802
Hepatocyte growth factor receptor P08581 MET_HUMAN Homo sapiens 4 0.7786
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7774
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7743
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7651
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7633
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7627
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7567
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7554
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7553
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7552
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7539
Serine/threonine-protein kinase PLK2 Q9NYY3 PLK2_HUMAN Homo sapiens 3 0.7530
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7483
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7429
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 4 0.7361
Gag-Pol polyprotein P04584 POL_HV2RO Human immunodeficiency virus type 2 subtype A 3 0.7356
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7337
Phosphodiesterase Q8WQX9 Q8WQX9_9TRYP Trypanosoma brucei 4 0.7319
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7304
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7291
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7291
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7290
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7289
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7287
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7287
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7260
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7245
Cytochrome P450 2C5 P00179 CP2C5_RABIT Oryctolagus cuniculus 3 0.7239
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.7235
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7228
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7224
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7215
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7188
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7151
Neuropilin-1 O14786 NRP1_HUMAN Homo sapiens 3 0.7100
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7076
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7065
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7051
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7049
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7045
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7035
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7012
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7011
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7010
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7001

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