1,2-dehydrobeninine - Compound Card

1,2-dehydrobeninine

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1,2-dehydrobeninine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles COc1cccc2c1N=C1[C@@]32CCN2[C@H]3[C@@]3(CC1)CCO[C@H]3CC2
InChI InChI=1S/C20H24N2O2/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/h2-4,16,18H,5-12H2,1H3/t16-,18-,19-,20-/m0/s1
InChIKey AVQFIGCLTPFSKP-LEAZDLGRSA-N
Formula C20H24N2O2
HBA 4
HBD 0
MW 324.42
Rotatable Bonds 1
TPSA 34.06
LogP 3.07
Number Rings 6
Number Aromatic Rings 1
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.65
Exact Mass 324.18
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: 163072097
Nmrshiftdb2: 70026278

No compound-protein relationship available.

Structure

SMILES: c1cccc(c1C234)N=C2CCC56C3N(CC4)CCC5OCC6

Level: 0

Mol. Weight: 324.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.73
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.840
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.57

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.630
Plasma Protein Binding
43.23
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
9.410
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.110
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.510
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.650
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
-5.930
Rat (Acute)
3.420
Rat (Chronic Oral)
1.430
Fathead Minnow
3.980
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
410.590
Hydration Free Energy
-4.210
Log(D) at pH=7.4
1.900
Log(P)
2.45
Log S
-2.54
Log(Vapor Pressure)
-7.34
Melting Point
155.7
pKa Acid
11.47
pKa Basic
8.34
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.9392
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.9392
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9271
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.9271
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8958
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8958
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8951
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8951
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8913
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8913
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8827
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8827
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8669
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8669
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8522
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8522
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8202
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.8202
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8134
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8134
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7854
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7854
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7847
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7847
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7806
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7806
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7519
Orotidine 5'-phosphate decarboxylase O58462 PYRF_PYRHO Pyrococcus horikoshii 3 0.7519
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7509
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7509
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7423
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7423
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7369
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7369
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7338
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7338
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7300
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7300
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7265
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 2 0.7265
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7258
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7258
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7248
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7248
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7212
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7212
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7197
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7197
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7126
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7126
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7100
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7100
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7051
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7051
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7031
Large structural protein Q91L20 Q91L20_9MONO Human metapneumovirus 3 0.7031
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7014
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7014
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7003
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7003

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