3-tropoyloxy-6-tigloyloxytropane - Compound Card

3-tropoyloxy-6-tigloyloxytropane

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3-tropoyloxy-6-tigloyloxytropane

Structure
Zoomed Structure
  • Family: Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(/C(=O)OC1CC2N(C1CC(C2)OC(=O)C(c1ccccc1)CO)C)\C
InChI InChI=1S/C22H29NO5/c1-4-14(2)21(25)28-20-11-16-10-17(12-19(20)23(16)3)27-22(26)18(13-24)15-8-6-5-7-9-15/h4-9,16-20,24H,10-13H2,1-3H3/b14-4+
InChIKey OPGJHCLCUNWOSH-LNKIKWGQSA-N
Formula C22H29NO5
HBA 6
HBD 1
MW 387.48
Rotatable Bonds 6
TPSA 76.07
LogP 2.42
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.55
Exact Mass 387.2
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]

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 245.32 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)
-4.89
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.72
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.4

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.51
Plasma Protein Binding
24.19
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
11.66
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.56
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.31
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
8.04
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
-7.55
Rat (Acute)
2.58
Rat (Chronic Oral)
1.8
Fathead Minnow
4.52
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
378.43
Hydration Free Energy
-6.08
Log(D) at pH=7.4
1.88
Log(P)
2.84
Log S
-2.29
Log(Vapor Pressure)
-8.38
Melting Point
122.3
pKa Acid
8.41
pKa Basic
9.03
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9352
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.9352
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9248
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9248
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9102
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.9102
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9093
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9093
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9044
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9044
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9044
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9044
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9023
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9023
Heat shock cognate 71 kDa protein P11142 HSP7C_HUMAN Homo sapiens 3 0.9010
Heat shock cognate 71 kDa protein P11142 HSP7C_HUMAN Homo sapiens 3 0.9010
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9000
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.9000
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8970
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8970
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8892
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8892
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8858
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8858
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8819
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.8819
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8779
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8779
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.8616
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.8616
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8427
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8427
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8399
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.8399
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8365
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8365
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8291
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8291
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7896
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7896
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7880
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 3 0.7880
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7864
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7864
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7735
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.7735
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7733
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7733
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7722
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7722
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7681
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7681
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.7671
4-alpha-glucanotransferase O87172 MALQ_THETH Thermus thermophilus 3 0.7671
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7652
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7652
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.7630
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.7630
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7628
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7628
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7617
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.7617
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7606
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7606
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7563
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7563
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7536
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7536
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7535
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7535
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7514
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7514
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7493
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7493
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7484
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7484
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7450
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7450
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7440
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7440
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7396
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7396
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7353
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7353
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7346
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 2 0.7346
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7345
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7345
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7339
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7339
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7323
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7323
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7320
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7320
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7283
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7283
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7282
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 2 0.7282
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7281
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7281
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7263
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7263
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7253
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 2 0.7253
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7250
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7250
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic Q1XH05 HGL1B_WHEAT Triticum aestivum 3 0.7207
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1b, chloroplastic Q1XH05 HGL1B_WHEAT Triticum aestivum 3 0.7207
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7198
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7198
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7197
Nitric oxide synthase 3 P29474 NOS3_HUMAN Homo sapiens 3 0.7197
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7185
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7185
4-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl glucoside beta-D-glucosidase 1, chloroplastic P49235 HGGL1_MAIZE Zea mays 2 0.7185
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 3 0.7185
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7175
Archaeal actin homolog Q9HKL4 ACTH_THEAC Thermoplasma acidophilum 2 0.7175
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7166
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7166
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 2 0.7165
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 2 0.7165
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7145
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7145
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7144
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7144
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7132
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7132
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7118
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7118
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7115
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7115
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7069
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7069
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7066
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7066
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7066
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7066
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7042
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7042
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7042
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7042
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7033
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 2 0.7033
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7030
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7030
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7027
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7027
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7022
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7022
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7020
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7020
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7018
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7018
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 2 0.7018
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7018
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7015
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 2 0.7015
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7014
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7014
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7010
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7010

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