3-tigloyloxy-6,7-epoxytropane - Compound Card

3-tigloyloxy-6,7-epoxytropane

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3-tigloyloxy-6,7-epoxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(/C(=O)OC1CC2C3C(C(C1)N2C)O3)\C
InChI InChI=1S/C13H19NO3/c1-4-7(2)13(15)16-8-5-9-11-12(17-11)10(6-8)14(9)3/h4,8-12H,5-6H2,1-3H3/b7-4+
InChIKey MAHIMWLGPHYDSP-QPJJXVBHSA-N
Formula C13H19NO3
HBA 4
HBD 0
MW 237.3
Rotatable Bonds 2
TPSA 42.07
LogP 1.11
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.77
Exact Mass 237.14
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: 91700481
Nmrshiftdb2: 70004763

No compound-protein relationship available.

Structure

SMILES: C12C(O2)C3CCCC1N3

Level: 0

Mol. Weight: 237.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.0
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.52
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.56

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.07
Plasma Protein Binding
0.74
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
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
13.51
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.25
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.12
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
7.55
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
4.37
Rat (Acute)
2.46
Rat (Chronic Oral)
0.59
Fathead Minnow
4.48
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
280.14
Hydration Free Energy
-7.66
Log(D) at pH=7.4
0.48
Log(P)
1.54
Log S
-0.66
Log(Vapor Pressure)
-4.63
Melting Point
69.55
pKa Acid
5.78
pKa Basic
6.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9646
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.9646
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9496
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.9496
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.9191
3-ketosteroid dehydrogenase Q9RA02 Q9RA02_RHOER Rhodococcus erythropolis 3 0.9191
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9103
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.9103
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9029
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.9029
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8750
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.8750
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8695
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8695
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8407
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8407
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8176
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8176
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8002
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8002
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7622
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7622
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7607
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7607
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7508
Camphor 5-monooxygenase P00183 CPXA_PSEPU Pseudomonas putida 3 0.7508
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7455
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7455
Vitamin D3 dihydroxylase P18326 CPXE_STRGO Streptomyces griseolus 3 0.7455
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7455
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7414
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7414
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7289
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7289
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7265
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 2 0.7265
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7257
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7257
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7199
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7199
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7184
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7184
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7167
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7167
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7123
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 2 0.7123
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7067
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7067
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7059
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7059
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7038
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7038
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7020
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7020
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7009
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7009

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