4'-hydroxylittorine - Compound Card

4'-hydroxylittorine

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4'-hydroxylittorine

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Alkaloid
Canonical Smiles O=C(C(O)C)O[C@@]1(CC2CCC(C1)N2C)c1ccc(cc1)O
InChI InChI=1S/C17H23NO4/c1-11(19)16(21)22-17(12-3-7-15(20)8-4-12)9-13-5-6-14(10-17)18(13)2/h3-4,7-8,11,13-14,19-20H,5-6,9-10H2,1-2H3
InChIKey MLAWOGWWJSYIKY-UHFFFAOYSA-N
Formula C17H23NO4
HBA 5
HBD 2
MW 305.37
Rotatable Bonds 3
TPSA 70.0
LogP 1.77
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 22
Formal Charge 0
Fraction CSP3 0.59
Exact Mass 305.16
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: 162817079

No compound-protein relationship available.

Structure

SMILES: C12CCC(N2)CC(C1)c3ccccc3

Level: 1

Mol. Weight: 305.37 g/mol

Structure

SMILES: C12CCC(N2)CCC1

Level: 0

Mol. Weight: 305.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 305.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.88
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
Non-Penetrable
Fraction Unbound (Human)
0.37
Plasma Protein Binding
1.57
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
12.54
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.32
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.9
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
1.54
Rat (Acute)
2.57
Rat (Chronic Oral)
1.94
Fathead Minnow
4.11
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
357.76
Hydration Free Energy
-9.41
Log(D) at pH=7.4
0.9
Log(P)
1.17
Log S
-1.86
Log(Vapor Pressure)
-6.78
Melting Point
174.47
pKa Acid
6.92
pKa Basic
8.61
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9537
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9537
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9524
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9524
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.9231
Chloramphenicol acetyltransferase P62577 CAT_ECOLX Escherichia coli 3 0.9231
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8853
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8853
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8807
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8807
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8712
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8712
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8692
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8692
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8621
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8621
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8398
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8398
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8302
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8302
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8302
Na(+):neurotransmitter symporter (Snf family) O67854 O67854_AQUAE Aquifex aeolicus 3 0.8302
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8231
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8231
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 4 0.8205
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q8ZMF7 ISPF_SALTY Salmonella typhimurium 4 0.8205
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8105
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8105
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.7970
Karilysin D0EM77 KLY_TANFA Tannerella forsythia 3 0.7970
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7806
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7806
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7761
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7761
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7758
Nucleoside diphosphate kinase A 2 P52175 NDKA2_BOVIN Bos taurus 3 0.7758
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.7674
Prenyltransferase Q4R2T2 Q4R2T2_STRC1 Streptomyces sp 3 0.7674
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7644
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7644
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7466
Type II methyltransferase M.TaqI P14385 MTTA_THEAQ Thermus aquaticus 3 0.7466
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7433
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7433
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7420
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7420
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7410
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7410
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7394
Orotidine 5'-phosphate decarboxylase O26232 PYRF_METTH Methanothermobacter thermautotrophicus 3 0.7394
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7392
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7392
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7385
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7385
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7367
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7367
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7330
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7330
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7329
Polyamine aminopropyltransferase Q5SK28 SPEE_THET8 Thermus thermophilus 3 0.7329
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7317
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7317
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7282
Leucine--tRNA ligase P07813 SYL_ECOLI Escherichia coli 3 0.7282
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7251
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7251
N-acetylhexosamine 1-kinase E8MF12 NAHK_BIFL2 Bifidobacterium longum subsp. longum 3 0.7218
N-acetylhexosamine 1-kinase E8MF12 NAHK_BIFL2 Bifidobacterium longum subsp. longum 3 0.7218
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7208
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7208
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7199
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7199
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7185
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 3 0.7185
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7123
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7123
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7117
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7117
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7113
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7113
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7102
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7102
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7095
Uridine phosphorylase P0A1F6 UDP_SALTY Salmonella typhimurium 3 0.7095
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.7058
7,8-dihydroneopterin aldolase J7VEZ6 J7VEZ6_BACCE Bacillus cereus BAG3X2-1 3 0.7058
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7054
Acidic mammalian chitinase Q9BZP6 CHIA_HUMAN Homo sapiens 3 0.7054
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7044
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7044
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7040
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7040
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7032
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.7032
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7005
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7005

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