Beninine - Compound Card

Beninine

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Beninine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COC1=CC=CC2=C1NC3C24CCN5C4C6(CC3)CCOC6CC5
InChI InChI=1S/C20H26N2O2/c1-23-14-4-2-3-13-17(14)21-15-5-7-19-9-12-24-16(19)6-10-22-11-8-20(13,15)18(19)22/h2-4,15-16,18,21H,5-12H2,1H3
InChIKey MPEAAEUXFWYMLD-UHFFFAOYSA-N
Formula C20H26N2O2
HBA 4
HBD 1
MW 326.44
Rotatable Bonds 1
TPSA 33.73
LogP 2.77
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 326.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Hedranthera barteri Apocynaceae Plantae 141540

Showing of synonyms

  • Agwada V, Patel MB, et al. (1970). Die Alkaloide aus Hedranthera barteri (Hook. f.) Pichonl. 139. Mitteilung uber die Alkaloide. Helvetica Chimica Acta,1970,53(7),1567-1577. [View]
Pubchem: 101297747

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)NC3CCC56C2N(CC4)CCC5OCC6

Level: 0

Mol. Weight: 326.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.87
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.160
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.53

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.490
Plasma Protein Binding
7.3
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.690
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.270
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.560
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.500
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
-3.630
Rat (Acute)
3.130
Rat (Chronic Oral)
1.530
Fathead Minnow
4.120
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
394.200
Hydration Free Energy
-5.500
Log(D) at pH=7.4
2.170
Log(P)
2.68
Log S
-2.15
Log(Vapor Pressure)
-7.26
Melting Point
152.03
pKa Acid
12.22
pKa Basic
8.47
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9655
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9655
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9635
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9635
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.9370
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.9370
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9326
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9326
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.9264
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.9264
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9204
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.9204
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9086
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9086
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.9041
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.9041
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8606
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8606
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8576
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8576
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8518
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8518
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8474
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8474
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8468
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8468
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8294
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8294
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8180
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8180
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8022
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.8022
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7983
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7983
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7928
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7928
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7807
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7807
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7758
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7758
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7700
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7700
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7583
Odorant binding protein ASP1 Q8WRW5 Q8WRW5_APIME Apis mellifera 3 0.7583
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7582
Class 10 plant pathogenesis-related protein 2B Q9LLQ2 P102B_LUPLU Lupinus luteus 2 0.7582
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7543
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7543
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7533
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.7533
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7528
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7528
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7519
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7519
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7510
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7510
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7504
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7504
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7500
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7500
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7488
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.7488
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7477
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7477
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7473
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7473
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7460
Fatty acid-binding protein 10-A, liver basic Q9I8L5 FA10A_DANRE Danio rerio 3 0.7460
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7449
Virulence sensor histidine kinase PhoQ P0DM80 PHOQ_SALTY Salmonella typhimurium 3 0.7449
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7422
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7422
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7408
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7408
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7408
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7408
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7404
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7404
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7382
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7382
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7346
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7346
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7340
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7340
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7327
dTDP-4-dehydro-6-deoxyglucose 3-epimerase Q5SFD1 CHMJ_STRBI Streptomyces bikiniensis 3 0.7327
Elongation factor 1-alpha O59153 EF1A_PYRHO Pyrococcus horikoshii 3 0.7292
Elongation factor 1-alpha O59153 EF1A_PYRHO Pyrococcus horikoshii 3 0.7292
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7276
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7276
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7270
16S rRNA (guanine(1405)-N(7))-methyltransferase Q763K9 Q763K9_ECOLX Escherichia coli 3 0.7270
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7266
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7266
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7257
SKP1-like protein 1A Q39255 SKP1A_ARATH Arabidopsis thaliana 3 0.7257
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7249
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7249
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7237
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7237
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 3 0.7216
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 3 0.7216
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7214
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7214
Elongation factor 1-alpha P02994 EF1A_YEAST Saccharomyces cerevisiae 3 0.7202
Elongation factor 1-alpha P02994 EF1A_YEAST Saccharomyces cerevisiae 3 0.7202
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7198
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7198
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7180
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7180
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 2 0.7173
Feruloyl esterase A O42807 FAEA_ASPNG Aspergillus niger 2 0.7173
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7171
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7171
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7161
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7161
Ribosome biogenesis GTPase YqeH D0VWU7 D0VWU7_GEOSE Geobacillus stearothermophilus 3 0.7160
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7160
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7160
Ribosome biogenesis GTPase YqeH D0VWU7 D0VWU7_GEOSE Geobacillus stearothermophilus 3 0.7160
Guanylate kinase P15454 KGUA_YEAST Saccharomyces cerevisiae 3 0.7150
Guanylate kinase P15454 KGUA_YEAST Saccharomyces cerevisiae 3 0.7150
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7142
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7142
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7127
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7127
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 3 0.7123
CalS13 Q8KND8 Q8KND8_MICEC Micromonospora echinospora 3 0.7123
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7111
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7111
Chromosome-associated kinesin KIF4 P33174 KIF4_MOUSE Mus musculus 2 0.7110
Chromosome-associated kinesin KIF4 P33174 KIF4_MOUSE Mus musculus 2 0.7110
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 2 0.7103
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 2 0.7103
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7101
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7101
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7089
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 2 0.7089
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7081
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7081
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7078
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7078
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 2 0.7066
Purine nucleoside phosphorylase, putative A2E7Y6 A2E7Y6_TRIVA Trichomonas vaginalis 2 0.7066
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7056
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7056
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7031
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7031
Bifunctional AAC/APH P0A0C1 AACA_STAAU Staphylococcus aureus 3 0.7031
Bifunctional AAC/APH P0A0C1 AACA_STAAU Staphylococcus aureus 3 0.7031
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7016
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7016
Uricase Q00511 URIC_ASPFL Aspergillus flavus 3 0.7001
Uricase Q00511 URIC_ASPFL Aspergillus flavus 3 0.7001

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