3-phenylacetoxy-6-hydroxytropane - Compound Card

3-phenylacetoxy-6-hydroxytropane

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3-phenylacetoxy-6-hydroxytropane

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O=C(Cc1ccccc1)OC1C[C@@H]2CC([C@H](C1)N2C)O
InChI InChI=1S/C16H21NO3/c1-17-12-8-13(10-14(17)15(18)9-12)20-16(19)7-11-5-3-2-4-6-11/h2-6,12-15,18H,7-10H2,1H3/t12-,13?,14+,15?/m1/s1
InChIKey NHJIGOBHFARUPD-JLVJUDLZSA-N
Formula C16H21NO3
HBA 4
HBD 1
MW 275.35
Rotatable Bonds 3
TPSA 49.77
LogP 1.37
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 20
Formal Charge 0
Fraction CSP3 0.56
Exact Mass 275.15
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: 91750089
Nmrshiftdb2: 70004757

No compound-protein relationship available.

Structure

SMILES: c1ccccc1CC(=O)OC(C2)CC(N3)CCC23

Level: 1

Mol. Weight: 275.35 g/mol

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 275.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 275.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.03
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.42
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.09

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.38
Plasma Protein Binding
46.31
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
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.38
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.47
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-1.55
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.97
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
1.47
Rat (Acute)
2.5
Rat (Chronic Oral)
1.87
Fathead Minnow
3.74
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
353.23
Hydration Free Energy
-10.67
Log(D) at pH=7.4
0.57
Log(P)
1.83
Log S
-1.73
Log(Vapor Pressure)
-6.93
Melting Point
120.38
pKa Acid
8.38
pKa Basic
8.39
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.9266
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.9266
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8633
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8633
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8600
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8600
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8432
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8432
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8375
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8375
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.8301
3-hydroxydecanoyl-[acyl-carrier-protein] dehydratase O33877 FABA_PSEAE Pseudomonas aeruginosa 3 0.8301
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7889
cAMP-dependent protein kinase type I-alpha regulatory subunit P00514 KAP0_BOVIN Bos taurus 3 0.7889
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7497
Adenylate cyclase type 5 P30803 ADCY5_CANLF Canis lupus familiaris 3 0.7497
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7469
Mitomycin-binding protein O05205 O05205_STRLA Streptomyces lavendulae 2 0.7469
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7463
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7463
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7389
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7389
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7348
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7348
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7306
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7306
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7295
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7295
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7294
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7294
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7235
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7235
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7196
Raucaffricine-O-beta-D-glucosidase Q9SPP9 RG1_RAUSE Rauvolfia serpentina 3 0.7196
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7182
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7182
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7163
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7163
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7123
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7123
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 2 0.7101
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 2 0.7101
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7090
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7090
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7088
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7088
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7072
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7072
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7069
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 2 0.7069
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7060
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7060
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7057
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7057
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7051
Acidic phospholipase A2 3 P60045 PA2A3_NAJSG Naja sagittifera 2 0.7051
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 2 0.7044
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 2 0.7044
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7040
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7040
Nucleoside diphosphate kinase Q9U1E1 Q9U1E1_LEIMA Leishmania major 3 0.7023
Nucleoside diphosphate kinase Q9U1E1 Q9U1E1_LEIMA Leishmania major 3 0.7023
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7013
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7013
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7009
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7009
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7003
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7003

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