Bicuculline - Compound Card

Bicuculline

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Bicuculline

Structure
Zoomed Structure
  • Family: Plantae - Papaveraceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Isoquinoline Alkaloid
Canonical Smiles CN1CCc2c([C@H]1[C@@H]1OC(=O)c3c1ccc1c3OCO1)cc1c(c2)OCO1
InChI InChI=1S/C20H17NO6/c1-21-5-4-10-6-14-15(25-8-24-14)7-12(10)17(21)18-11-2-3-13-19(26-9-23-13)16(11)20(22)27-18/h2-3,6-7,17-18H,4-5,8-9H2,1H3/t17-,18+/m0/s1
InChIKey IYGYMKDQCDOMRE-ZWKOTPCHSA-N
Formula C20H17NO6
HBA 7
HBD 0
MW 367.36
Rotatable Bonds 1
TPSA 66.46
LogP 2.58
Number Rings 6
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.35
Exact Mass 367.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Fumaria parviflora Fumariaceae Plantae 1464625
2 Fumaria parviflora Papaveraceae Plantae 1464625

Showing of synonyms

  • Elsaid M.B, Elnaggar D.M, et al. (2022). Production of isoquinoline alkaloids from the in vitro conserved Fumaria parviflora and their in vitro wound healing activity. Natural product research, 2022, 36(10), 2575-2579. [View] [PubMed]
Pubchem: 10237
Kegg Ligand: C09364
Chebi: 3092
Nmrshiftdb2: 60026162
Metabolights: MTBLC3092
Drugbank: DB11562
Pdb Ligand: H0Z
Bindingdb: 50000693
Selleck: bicuculline
CPRiL: 2418
Structure

SMILES: O1COc(c1c23)ccc2C(OC3=O)C(NCC4)c(c5)c4cc(c56)OCO6

Level: 1

Mol. Weight: 367.36 g/mol

Structure

SMILES: O1COc(c1c23)ccc2COC3=O

Level: 0

Mol. Weight: 367.36 g/mol

Structure

SMILES: O1COc(c12)cc3c(c2)CCNC3

Level: 0

Mol. Weight: 367.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.89
Plasma Protein Binding
67.17
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
15.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.41
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.47
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
-20.78
Rat (Acute)
2.51
Rat (Chronic Oral)
0.96
Fathead Minnow
4.61
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
449.75
Hydration Free Energy
-5.16
Log(D) at pH=7.4
2.7
Log(P)
2.23
Log S
-4.39
Log(Vapor Pressure)
-10.14
Melting Point
179.16
pKa Acid
8.85
pKa Basic
5.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9191
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9093
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.8986
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8918
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8884
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8858
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.8846
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.8758
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8714
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8712
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8696
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8680
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.8657
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.8607
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8519
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8378
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8343
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8256
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8211
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8197
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.8114
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8093
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.8081
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8060
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8057
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8047
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.8011
(RS)-norcoclaurine 6-O-methyltransferase Q5C9L7 6OMT_THLFG Thalictrum flavum subsp. glaucum 4 0.7916
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.7896
Mitomycin biosynthesis 6-O-methyltransferase Q9X5T6 MMCR_STRLA Streptomyces lavendulae 3 0.7894
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7826
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7811
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7680
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7645
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7639
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7632
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7622
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7611
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7594
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7566
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7554
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7547
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7537
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7525
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7524
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7451
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7445
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7440
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7435
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7418
Abscisic acid receptor PYL1 Q8VZS8 PYL1_ARATH Arabidopsis thaliana 3 0.7402
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7381
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7358
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7351
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7344
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 4 0.7328
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7279
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7261
Protein LlR18A P52778 L18A_LUPLU Lupinus luteus 3 0.7231
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7229
Enoyl-ACP reductase Q9BJJ9 Q9BJJ9_PLAFA Plasmodium falciparum 3 0.7217
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7203
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.7199
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7192
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7192
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7191
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7188
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7185
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7177
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 3 0.7176
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7167
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7159
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7158
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7156
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7151
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7145
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7144
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7140
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7140
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7138
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7133
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7131
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7119
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7118
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7108
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7103
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7097
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7078
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7070
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7068
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7062
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7045
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7041
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7029
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7020
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7016
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7011
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7003

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