Atropine - Compound Card

Atropine

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Atropine

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles OCC(c1ccccc1)C(=O)OC1C[C@@H]2CC[C@H](C1)N2C
InChI InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15?,16?
InChIKey RKUNBYITZUJHSG-PJPHBNEVSA-N
Formula C17H23NO3
HBA 4
HBD 1
MW 289.38
Rotatable Bonds 4
TPSA 49.77
LogP 1.93
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 289.17
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: 174174
Nmrshiftdb2: 70004804
Bindingdb: 200229
CPRiL: 579
Structure

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

Level: 1

Mol. Weight: 289.38 g/mol

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 289.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 289.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.02
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.48
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.65

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.27
Plasma Protein Binding
44.8
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
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.3
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.2
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-2.97
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
4.37
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
0.66
Rat (Acute)
2.8
Rat (Chronic Oral)
2.04
Fathead Minnow
3.93
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
353.38
Hydration Free Energy
-9.28
Log(D) at pH=7.4
0.66
Log(P)
1.96
Log S
-1.83
Log(Vapor Pressure)
-6.52
Melting Point
122.08
pKa Acid
9.48
pKa Basic
9.15
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8982
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.8982
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8747
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8747
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8541
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8541
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8537
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8537
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8472
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8472
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8330
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8330
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8275
Gag-Pol polyprotein P0C6F2 POL_HV1LW Human immunodeficiency virus type 1 group M subtype B 3 0.8275
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8136
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8136
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8108
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8108
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.8108
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8108
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8069
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8069
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.8020
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.8020
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7997
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7997
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7908
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 3 0.7908
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7867
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7867
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7842
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7842
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7837
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7837
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7562
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7562
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7554
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7554
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7545
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7545
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7543
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7543
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7525
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7525
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7520
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7520
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7509
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7509
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7470
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7470
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7398
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7398
Endoglycoceramidase II O33853 O33853_RHOSO Rhodococcus sp 3 0.7388
Endoglycoceramidase II O33853 O33853_RHOSO Rhodococcus sp 3 0.7388
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 4 0.7377
Purine nucleoside phosphorylase P50389 PNPH_SACS2 Saccharolobus solfataricus 4 0.7377
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7332
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7332
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7327
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7327
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7321
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7321
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7314
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7314
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7268
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7268
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7237
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7237
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7208
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7208
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7195
Bifunctional dihydrofolate reductase-thymidylate synthase Q27793 DRTS_TRYCR Trypanosoma cruzi 3 0.7195
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7189
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7189
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7168
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7168
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7164
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7164
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7125
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7125
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7112
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 2 0.7112
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7110
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7110
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7107
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7107
Bifunctional dihydrofolate reductase-thymidylate synthase A7UD81 A7UD81_PLAFA Plasmodium falciparum 3 0.7107
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7107
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7094
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 3 0.7094
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7092
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 2 0.7092
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7070
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7070
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7050
Focal adhesion kinase 1 Q05397 FAK1_HUMAN Homo sapiens 2 0.7050
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7037
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7037
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7032
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7032
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7015
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7015
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7003
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7003

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