3alpha-tropoyloxy-6beta-isovaleroyloxytropane - Compound Card

3alpha-tropoyloxy-6beta-isovaleroyloxytropane

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3alpha-tropoyloxy-6beta-isovaleroyloxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles OCC(c1ccccc1)C(=O)O[C@H]1CC2C[C@@H](C(C1)N2C)OC(=O)CC(C)C
InChI InChI=1S/C22H31NO5/c1-14(2)9-21(25)28-20-11-16-10-17(12-19(20)23(16)3)27-22(26)18(13-24)15-7-5-4-6-8-15/h4-8,14,16-20,24H,9-13H2,1-3H3/t16?,17-,18?,19?,20-/m0/s1
InChIKey UOEYCNAEZZOSJM-BHZIUBDXSA-N
Formula C22H31NO5
HBA 6
HBD 1
MW 389.49
Rotatable Bonds 7
TPSA 76.07
LogP 2.5
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 28
Formal Charge 0
Fraction CSP3 0.64
Exact Mass 389.22
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: 162817078
Nmrshiftdb2: 70004767

No compound-protein relationship available.

Structure

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

Level: 1

Mol. Weight: 389.49 g/mol

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 389.49 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 389.49 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.85
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.73
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)
0.55
Plasma Protein Binding
54.32
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
12.51
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.64
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.18
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.98
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
-9.13
Rat (Acute)
2.67
Rat (Chronic Oral)
1.83
Fathead Minnow
4.09
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
373.88
Hydration Free Energy
-6.28
Log(D) at pH=7.4
1.74
Log(P)
3.06
Log S
-2.32
Log(Vapor Pressure)
-8.36
Melting Point
114.24
pKa Acid
8.29
pKa Basic
8.71
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 0.9182
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.9182
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.9044
Gag-Pol polyprotein P03369 POL_HV1A2 Human immunodeficiency virus type 1 group M subtype B 3 0.9044
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9034
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.9034
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8835
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8835
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8810
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8810
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8720
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8720
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8696
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8696
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8631
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8631
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8631
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8631
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8625
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8625
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8481
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8481
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8305
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8305
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8251
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8251
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8091
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8091
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8084
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8084
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.8073
rRNA methylase Q8DSS3 Q8DSS3_STRMU Streptococcus mutans serotype c 2 0.8073
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8071
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8071
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8063
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8063
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7970
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7970
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7943
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7943
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7898
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7898
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7803
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7803
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7767
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7767
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7677
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7677
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7656
N-acetyltransferase domain-containing protein Q9HV14 Q9HV14_PSEAE Pseudomonas aeruginosa 2 0.7656
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7654
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7654
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7622
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7622
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 4 0.7595
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 4 0.7595
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7560
Agglutinin alpha chain P18674 LECA_MACPO Maclura pomifera 3 0.7560
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7524
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7524
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7481
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7481
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7476
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7476
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7471
4-hydroxyphenylacetate 3-monooxygenase, reductase component Q5SJP7 HPAC_THET8 Thermus thermophilus 3 0.7471
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7424
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7424
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7386
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7386
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7343
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7343
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7332
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7332
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7307
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7307
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7299
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7299
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7273
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7273
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7270
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7270
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7257
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7257
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7246
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7246
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.7246
Cystathionine gamma-synthase P56069 METB_HELPY Helicobacter pylori 3 0.7246
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7245
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 2 0.7245
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7233
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7233
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7222
Flavin reductase like domain-containing protein Q4UKE8 Q4UKE8_RICFE Rickettsia felis 3 0.7222
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7196
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7196
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 0.7172
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7172
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 0.7172
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7172
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7164
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7164
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.7117
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.7117
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7101
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7101
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7100
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.7100
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7086
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7086
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7080
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7080
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7073
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7073
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 2 0.7043
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 2 0.7043
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7042
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7042
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7020
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7020
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7017
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7017

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