3-tigloyloxy-6-propionyloxytropane - Compound Card

3-tigloyloxy-6-propionyloxytropane

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3-tigloyloxy-6-propionyloxytropane

Structure
Zoomed Structure
  • Family: Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles CCC(=O)OC1CC2N(C1CC(C2)OC(=O)/C(=C/C)/C)C
InChI InChI=1S/C16H25NO4/c1-5-10(3)16(19)20-12-7-11-8-14(21-15(18)6-2)13(9-12)17(11)4/h5,11-14H,6-9H2,1-4H3/b10-5+
InChIKey AUZMUMNBZCSKGT-BJMVGYQFSA-N
Formula C16H25NO4
HBA 5
HBD 0
MW 295.38
Rotatable Bonds 4
TPSA 55.84
LogP 2.05
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 21
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 295.18
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: 5368889
Nmrshiftdb2: 70004795

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 111.19 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.81
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.68
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
22.31
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
7.52
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.02
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.4
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.68
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
4.07
Rat (Acute)
2.15
Rat (Chronic Oral)
1.31
Fathead Minnow
4.28
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
301.91
Hydration Free Energy
-6.72
Log(D) at pH=7.4
0.97
Log(P)
2.68
Log S
-1.71
Log(Vapor Pressure)
-5.22
Melting Point
87.62
pKa Acid
9.03
pKa Basic
8.1
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7616
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7616
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 3 0.7542
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 3 0.7542
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7483
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7483
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7363
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7363
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7267
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7267
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7102
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7102
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7016
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7016

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