3,6-ditigloyloxy-7-hydroxytropane - Compound Card

3,6-ditigloyloxy-7-hydroxytropane

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3,6-ditigloyloxy-7-hydroxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(/C(=O)OC1CC2N(C(C1)C(C2O)OC(=O)/C(=C/C)/C)C)\C
InChI InChI=1S/C18H27NO5/c1-6-10(3)17(21)23-12-8-13-15(20)16(14(9-12)19(13)5)24-18(22)11(4)7-2/h6-7,12-16,20H,8-9H2,1-5H3/b10-6+,11-7+
InChIKey FRQMNJFBOJQRAQ-JMQWPVDRSA-N
Formula C18H27NO5
HBA 6
HBD 1
MW 337.42
Rotatable Bonds 4
TPSA 76.07
LogP 1.58
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.67
Exact Mass 337.19
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: 12960452
Chebi: 169768
Nmrshiftdb2: 70004790

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 337.42 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.71
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.71
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.81

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.45
Plasma Protein Binding
17.42
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
6.72
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.15
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.64
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
7.49
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
3.97
Rat (Acute)
2.46
Rat (Chronic Oral)
1.42
Fathead Minnow
4.63
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
339.84
Hydration Free Energy
-8.6
Log(D) at pH=7.4
1.44
Log(P)
2.6
Log S
-1.87
Log(Vapor Pressure)
-6.63
Melting Point
123.14
pKa Acid
7.82
pKa Basic
7.72
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8795
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8795
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8461
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8461
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8370
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8370
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8250
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8250
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8249
Reaction center protein L chain P0C0Y7 RCEH_RHOSH Rhodobacter sphaeroides 3 0.8249
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8060
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.8060
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8050
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8050
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8037
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8037
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7807
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7807
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7774
Acetylcholinesterase P04058 ACES_TETCF Tetronarce californica 3 0.7774
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7713
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7713
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7516
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7516
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7501
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7501
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7458
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7458
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7369
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7369
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7349
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7349
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7309
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7309
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7195
Methyl-branched lipid omega-hydroxylase P9WPP3 CP124_MYCTU Mycobacterium tuberculosis 3 0.7195
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7171
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7171
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7159
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7159
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7114
Jasmonoyl--L-amino acid synthetase JAR1 Q9SKE2 JAR1_ARATH Arabidopsis thaliana 3 0.7114
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7102
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7102
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7019
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7019

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