3-(2'-phenylpropionyloxy)tropane - Compound Card

3-(2'-phenylpropionyloxy)tropane

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3-(2'-phenylpropionyloxy)tropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CC(c1ccccc1)C(=O)OC1CC2CCC(C1)N2C
InChI InChI=1S/C17H23NO2/c1-12(13-6-4-3-5-7-13)17(19)20-16-10-14-8-9-15(11-16)18(14)2/h3-7,12,14-16H,8-11H2,1-2H3
InChIKey ABQUDUAAINLKTQ-UHFFFAOYSA-N
Formula C17H23NO2
HBA 3
HBD 0
MW 273.38
Rotatable Bonds 3
TPSA 29.54
LogP 2.96
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 273.17
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Datura stramonium Solanaceae Plantae 4076

Showing of synonyms

  • El Bazaoui A, Bellimam MA, et al. (2011). Nine new tropane alkaloids from Datura stramonium L. identified by GC/MS. Fitoterapia,2011,82(2),193-197. [View] [PubMed]
Pubchem: 10401092
Nmrshiftdb2: 70004775

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(=O)OC(C2)CC(N3)CCC23

Level: 1

Mol. Weight: 273.38 g/mol

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 273.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 273.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.47
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.23

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.41
Plasma Protein Binding
32.27
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.55
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.72
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.16
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
4.03
Rat (Acute)
2.68
Rat (Chronic Oral)
1.74
Fathead Minnow
4.0
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
315.26
Hydration Free Energy
-7.34
Log(D) at pH=7.4
1.7
Log(P)
2.82
Log S
-2.03
Log(Vapor Pressure)
-5.26
Melting Point
101.19
pKa Acid
9.56
pKa Basic
9.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.8810
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.8810
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8431
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8431
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8389
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8389
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8298
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8298
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8164
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8164
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7929
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 2 0.7929
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7881
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7881
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7855
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7855
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7849
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7849
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7811
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7811
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7800
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7800
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7703
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7703
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7630
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 2 0.7630
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7627
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7627
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7597
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7597
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7572
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7572
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7547
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7547
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7545
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7545
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7544
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7544
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7533
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7533
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7516
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7516
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7483
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7483
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7463
Aromatic-amino-acid aminotransferase P95468 TYRB_PARDE Paracoccus denitrificans 2 0.7463
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7462
IAG-nucleoside hydrolase Q9GPQ4 Q9GPQ4_TRYVI Trypanosoma vivax 3 0.7462
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7461
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7461
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7424
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7424
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7417
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7417
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7412
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7412
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7410
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7410
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7389
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7389
Endoglycoceramidase II O33853 O33853_RHOSO Rhodococcus sp 3 0.7386
Endoglycoceramidase II O33853 O33853_RHOSO Rhodococcus sp 3 0.7386
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7374
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7374
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7367
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7367
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7337
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7337
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7333
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7333
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7326
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7326
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7325
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7325
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7260
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7260
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7239
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7239
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7236
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7236
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7236
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7236
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7228
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7228
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7213
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7213
Heat shock 70 kDa protein 1A P0DMV8 HS71A_HUMAN Homo sapiens 3 0.7198
Heat shock 70 kDa protein 1A P0DMV8 HS71A_HUMAN Homo sapiens 3 0.7198
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7186
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7186
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 2 0.7180
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 2 0.7180
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7164
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7164
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7163
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7163
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7150
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7150
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7145
Ceramide transfer protein Q9Y5P4 CERT_HUMAN Homo sapiens 3 0.7145
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7111
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7111
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7109
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7109
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7104
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7104
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7100
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7100
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7090
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7090
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7089
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7089
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7082
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 2 0.7082
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7067
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7067
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7061
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7061
Heat shock cognate 71 kDa protein P19120 HSP7C_BOVIN Bos taurus 2 0.7051
Heat shock cognate 71 kDa protein P19120 HSP7C_BOVIN Bos taurus 2 0.7051
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7050
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 2 0.7050
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7050
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7050
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7048
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7048
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7045
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7045
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7042
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7042
Lipoprotein E P26093 HEL_HAEIN Haemophilus influenzae 3 0.7021
Lipoprotein E P26093 HEL_HAEIN Haemophilus influenzae 3 0.7021
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7020
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7020
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 2 0.7007
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 2 0.7007
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7004
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7004

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