3-tigloyloxy-6-(2'-methylbutyryloxy)tropane - Compound Card

3-tigloyloxy-6-(2'-methylbutyryloxy)tropane

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3-tigloyloxy-6-(2'-methylbutyryloxy)tropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CCC(C(=O)OC1CC2N(C1CC(C2)OC(=O)/C(=C/C)/C)C)C
InChI InChI=1S/C18H29NO4/c1-6-11(3)17(20)22-14-8-13-9-16(15(10-14)19(13)5)23-18(21)12(4)7-2/h6,12-16H,7-10H2,1-5H3/b11-6+
InChIKey LWJJYAYQOTXATC-IZZDOVSWSA-N
Formula C18H29NO4
HBA 5
HBD 0
MW 323.43
Rotatable Bonds 5
TPSA 55.84
LogP 2.69
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.78
Exact Mass 323.21
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: 91700476
Nmrshiftdb2: 70004800

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 323.43 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.7
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.25

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.33
Plasma Protein Binding
26.34
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
8.78
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.19
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.44
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.88
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
3.96
Rat (Acute)
2.44
Rat (Chronic Oral)
1.36
Fathead Minnow
4.36
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
312.74
Hydration Free Energy
-5.82
Log(D) at pH=7.4
1.81
Log(P)
3.66
Log S
-2.27
Log(Vapor Pressure)
-5.49
Melting Point
86.7
pKa Acid
9.17
pKa Basic
8.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9229
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.9229
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8416
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8416
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7962
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7962
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7741
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7741
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7692
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7692
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7634
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7634
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7554
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7554
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7529
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7529
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7364
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7364
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7302
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7302
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7235
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7235
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7229
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 2 0.7229
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7204
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7204
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7144
Abscisic acid receptor PYL3 Q9SSM7 PYL3_ARATH Arabidopsis thaliana 3 0.7144
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7122
Abscisic acid receptor PYR1 O49686 PYR1_ARATH Arabidopsis thaliana 3 0.7122
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7080
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7080
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7031
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7031

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