3-tigloyloxy-6-acetoxytropane - Compound Card

3-tigloyloxy-6-acetoxytropane

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3-tigloyloxy-6-acetoxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(/C(=O)O[C@H]1C[C@@H]2C[C@H]([C@H](C1)N2C)OC(=O)C)\C
InChI InChI=1S/C15H23NO4/c1-5-9(2)15(18)20-12-6-11-7-14(19-10(3)17)13(8-12)16(11)4/h5,11-14H,6-8H2,1-4H3/b9-5+/t11-,12+,13+,14-/m1/s1
InChIKey JZEPGIHACXZLFL-NYKPPTNSSA-N
Formula C15H23NO4
HBA 5
HBD 0
MW 281.35
Rotatable Bonds 3
TPSA 55.84
LogP 1.66
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.73
Exact Mass 281.16
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: 91750082
Nmrshiftdb2: 70004785

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 281.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.9
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.62
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)
0.28
Plasma Protein Binding
26.59
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
7.8
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.08
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.54
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.93
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
0.27
Rat (Acute)
2.11
Rat (Chronic Oral)
1.33
Fathead Minnow
3.94
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
300.81
Hydration Free Energy
-7.53
Log(D) at pH=7.4
0.34
Log(P)
2.1
Log S
-1.55
Log(Vapor Pressure)
-5.29
Melting Point
114.6
pKa Acid
8.73
pKa Basic
7.83
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8669
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8669
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7240
Muconolactone Delta-isomerase Q8G9L0 Q8G9L0_RHOOP Rhodococcus opacus 2 0.7240
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7139
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7139
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7121
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7121

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