3-tigloyloxy-6-isobutyryloxytropane - Compound Card

3-tigloyloxy-6-isobutyryloxytropane

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3-tigloyloxy-6-isobutyryloxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(/C(=O)OC1CC2CC(C(C1)N2C)OC(=O)C(C)C)\C
InChI InChI=1S/C17H27NO4/c1-6-11(4)17(20)21-13-7-12-8-15(14(9-13)18(12)5)22-16(19)10(2)3/h6,10,12-15H,7-9H2,1-5H3/b11-6+
InChIKey ADNCMUUXIVQCLS-IZZDOVSWSA-N
Formula C17H27NO4
HBA 5
HBD 0
MW 309.41
Rotatable Bonds 4
TPSA 55.84
LogP 2.3
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.76
Exact Mass 309.19
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: 129662878

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 309.41 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.33

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.32
Plasma Protein Binding
25.32
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
8.54
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.26
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.39
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.74
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
3.8
Rat (Acute)
2.31
Rat (Chronic Oral)
1.36
Fathead Minnow
4.39
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
306.59
Hydration Free Energy
-6.21
Log(D) at pH=7.4
1.26
Log(P)
3.13
Log S
-1.91
Log(Vapor Pressure)
-5.3
Melting Point
97.84
pKa Acid
8.96
pKa Basic
8.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7221
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7221
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7146
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7146
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7123
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7123

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