3alpha-hydroxy-6beta-tigloyloxytropane - Compound Card

3alpha-hydroxy-6beta-tigloyloxytropane

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3alpha-hydroxy-6beta-tigloyloxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles C/C=C(/C(=O)OCN1C2CC(C[C@@H]1C2)O)\C
InChI InChI=1S/C12H19NO3/c1-3-8(2)12(15)16-7-13-9-4-10(13)6-11(14)5-9/h3,9-11,14H,4-7H2,1-2H3/b8-3+/t9-,10?,11?/m0/s1
InChIKey SNECHSBCFLJKND-PVEZAKGCSA-N
Formula C12H19NO3
HBA 4
HBD 1
MW 225.29
Rotatable Bonds 3
TPSA 49.77
LogP 1.05
Number Rings 3
Number Aromatic Rings 0
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.75
Exact Mass 225.14
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: 91750074
Nmrshiftdb2: 70004803

No compound-protein relationship available.

Structure

SMILES: C12CC(N2)CCC1

Level: 0

Mol. Weight: 225.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.11
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.46
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.26

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.24
Plasma Protein Binding
22.79
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
4.79
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.72
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.15
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.3
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
3.47
Rat (Acute)
2.03
Rat (Chronic Oral)
1.55
Fathead Minnow
3.97
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
284.59
Hydration Free Energy
-7.97
Log(D) at pH=7.4
0.46
Log(P)
1.06
Log S
-1.08
Log(Vapor Pressure)
-4.82
Melting Point
126.07
pKa Acid
8.98
pKa Basic
8.52
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9298
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.9298
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8990
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 3 0.8990
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8950
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8950
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8829
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.8829
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8363
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.8363
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8273
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8273
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8212
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.8212
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7510
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7510
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7455
Lysosomal acid glucosylceramidase P04062 GLCM_HUMAN Homo sapiens 3 0.7455
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7391
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7391
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7344
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.7344
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7306
Carnitine O-acetyltransferase P47934 CACP_MOUSE Mus musculus 2 0.7306
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7183
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7183
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7061
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7061
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7056
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7056
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7019
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7019
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7017
Angiotensin-converting enzyme Q10714 ACE_DROME Drosophila melanogaster 3 0.7017

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