Apoatropine - Compound Card

Apoatropine

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Apoatropine

Structure
Zoomed Structure
  • Family: Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CN1C2CCC1CC(C2)OC(=O)C(=C)c1ccccc1
InChI InChI=1S/C17H21NO2/c1-12(13-6-4-3-5-7-13)17(19)20-16-10-14-8-9-15(11-16)18(14)2/h3-7,14-16H,1,8-11H2,2H3
InChIKey WPUIZWXOSDVQJU-UHFFFAOYSA-N
Formula C17H21NO2
HBA 3
HBD 0
MW 271.36
Rotatable Bonds 3
TPSA 29.54
LogP 2.87
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.47
Exact Mass 271.16
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: 64695
Kegg Ligand: C10843
Chebi: 2780
Nmrshiftdb2: 60027297
CPRiL: 412296
Structure

SMILES: c1ccccc1C(=C)C(=O)OC(C2)CC(N3)CCC23

Level: 1

Mol. Weight: 257.33 g/mol

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 111.19 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 78.11 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.77
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
-2.27

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.48
Plasma Protein Binding
38.66
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
9.06
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.65
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.79
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.9
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
4.59
Rat (Acute)
2.79
Rat (Chronic Oral)
1.89
Fathead Minnow
4.13
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
318.01
Hydration Free Energy
-7.32
Log(D) at pH=7.4
1.97
Log(P)
2.88
Log S
-2.37
Log(Vapor Pressure)
-5.46
Melting Point
102.23
pKa Acid
8.18
pKa Basic
8.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8559
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.8559
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8323
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8323
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8209
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8209
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7892
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 2 0.7892
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7824
Cytochrome P450 2A6 P11509 CP2A6_HUMAN Homo sapiens 3 0.7824
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7791
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7791
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7725
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7725
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7553
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7553
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7538
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7538
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7533
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7533
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7517
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7517
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7502
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7502
Lethal factor P15917 LEF_BACAN Bacillus anthracis 2 0.7461
Lethal factor P15917 LEF_BACAN Bacillus anthracis 2 0.7461
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7448
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7448
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7448
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7448
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7447
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7447
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7409
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7409
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7399
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7399
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7398
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.7398
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7386
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7386
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7366
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7366
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7362
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 2 0.7362
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7356
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7356
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7331
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7331
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7327
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7327
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7314
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7314
Purine nucleoside phosphorylase DeoD-type 1 Q9KPM0 DEOD1_VIBCH Vibrio cholerae serotype O1 3 0.7309
Purine nucleoside phosphorylase DeoD-type 1 Q9KPM0 DEOD1_VIBCH Vibrio cholerae serotype O1 3 0.7309
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7280
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 2 0.7280
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7270
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7270
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7265
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7265
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7257
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7257
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7256
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7256
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7252
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7252
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7249
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7249
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7243
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7243
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7241
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7241
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7237
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7237
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7198
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7198
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7179
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7179
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7176
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7176
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7172
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7172
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7171
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7171
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 2 0.7169
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 2 0.7169
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7167
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 2 0.7167
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7166
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7166
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7159
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7159
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7155
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7155
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7153
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7153
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7151
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7151
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7150
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7150
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7142
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7142
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7128
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7128
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7124
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7124
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7121
Renin P00797 RENI_HUMAN Homo sapiens 2 0.7121
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 2 0.7119
Snake venom metalloproteinase atrolysin-D P15167 VM1AD_CROAT Crotalus atrox 2 0.7119
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7119
Pyridoxal kinase O00764 PDXK_HUMAN Homo sapiens 2 0.7119
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7114
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7114
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7112
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7112
Threonine synthase 1, chloroplastic Q9S7B5 THRC1_ARATH Arabidopsis thaliana 2 0.7109
Threonine synthase 1, chloroplastic Q9S7B5 THRC1_ARATH Arabidopsis thaliana 2 0.7109
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7106
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7106
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7102
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7102
Heat shock 70 kDa protein 1A P0DMV8 HS71A_HUMAN Homo sapiens 3 0.7099
Heat shock 70 kDa protein 1A P0DMV8 HS71A_HUMAN Homo sapiens 3 0.7099
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7098
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7098
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7094
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7094
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7093
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7093
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7090
Alanine racemase Q180W0 Q180W0_CLOD6 Clostridioides difficile 2 0.7090
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7089
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7089
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7088
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 2 0.7088
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7078
Inosine-5'-monophosphate dehydrogenase P50097 IMDH_TRIFO Tritrichomonas foetus 2 0.7078
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 2 0.7076
Carbonic anhydrase Q39588 Q39588_CHLRE Chlamydomonas reinhardtii 2 0.7076
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7075
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7075
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7061
Unconventional myosin-Va Q02440 MYO5A_CHICK Gallus gallus 2 0.7061
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7060
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7060
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7049
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 2 0.7049
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 2 0.7048
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 2 0.7048
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7039
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 2 0.7039
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7035
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 2 0.7035
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 2 0.7035
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7035
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7031
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7031
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 2 0.7023
Nicotinamide phosphoribosyltransferase P43490 NAMPT_HUMAN Homo sapiens 2 0.7023
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7020
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7020
VioE domain-containing protein Q7NSZ5 Q7NSZ5_CHRVO Chromobacterium violaceum 2 0.7007
VioE domain-containing protein Q7NSZ5 Q7NSZ5_CHRVO Chromobacterium violaceum 2 0.7007

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