Touruosamine - Compound Card

Touruosamine

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Touruosamine

Structure
Zoomed Structure
  • Family: Plantae - Mesembryanthemaceae-Aizoaceae
  • Kingdom: Plantae
  • Class: Alkaloid
    • Subclass: Mesemberine Alkaloid
Canonical Smiles CNCCC1(CCCc2c1cccn2)c1ccc(c(c1)OC)OC
InChI InChI=1S/C20H26N2O2/c1-21-13-11-20(10-4-7-17-16(20)6-5-12-22-17)15-8-9-18(23-2)19(14-15)24-3/h5-6,8-9,12,14,21H,4,7,10-11,13H2,1-3H3
InChIKey LBNZFDKJDNQRPO-UHFFFAOYSA-N
Formula C20H26N2O2
HBA 4
HBD 1
MW 326.44
Rotatable Bonds 6
TPSA 43.38
LogP 3.33
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.45
Exact Mass 326.2
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Mesembryanthemum cordifolium-Aptenia cordifolia Mesembryanthemaceae-Aizoaceae Plantae 3543

Showing of synonyms

  • Said A.A.E, Ali T.F.S, et al. (2021). Antidepressant potential of Mesembryanthemum cordifolium roots assisted by metabolomic analysis and virtual screening. Natural product research, 2021, 35(23), 5493-5497. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccnc(c12)CCCC2c3ccccc3

Level: 1

Mol. Weight: 326.44 g/mol

Structure

SMILES: C1CCCc(c12)nccc2

Level: 0

Mol. Weight: 326.44 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 326.44 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.86
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.74
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.44

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.93
Plasma Protein Binding
54.46
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.38
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.75
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.51
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
6.47
Micronucleos
Safe
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
Toxic
T. Pyriformis
1.73
Rat (Acute)
2.83
Rat (Chronic Oral)
1.66
Fathead Minnow
4.57
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
379.78
Hydration Free Energy
-8.08
Log(D) at pH=7.4
2.27
Log(P)
2.82
Log S
-2.37
Log(Vapor Pressure)
-6.6
Melting Point
111.38
pKa Acid
11.78
pKa Basic
9.38
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.9571
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.9272
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9270
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.9268
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9265
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9238
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.9211
Histamine N-methyltransferase P50135 HNMT_HUMAN Homo sapiens 3 0.9146
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9136
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9110
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9088
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.9045
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.9023
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8992
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8962
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.8919
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.8909
Protein S100-A4 P26447 S10A4_HUMAN Homo sapiens 3 0.8847
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8846
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8769
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.8736
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8701
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8609
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8605
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8599
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8520
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8458
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 4 0.8392
Cytochrome P450 2D6 P10635 CP2D6_HUMAN Homo sapiens 3 0.8368
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8342
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.8341
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8304
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8268
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8238
Prostaglandin G/H synthase 1 P05979 PGH1_SHEEP Ovis aries 3 0.8206
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8133
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8125
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8105
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8093
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.8081
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.8075
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8060
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8024
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8019
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7987
Albumin P02768 ALBU_HUMAN Homo sapiens 4 0.7974
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7927
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7909
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7901
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7894
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7846
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7834
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7824
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7823
Endoplasmin P14625 ENPL_HUMAN Homo sapiens 3 0.7795
Activin receptor type-1 Q04771 ACVR1_HUMAN Homo sapiens 3 0.7795
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7789
Putative ketoacyl reductase P16544 ACT3_STRCO Streptomyces coelicolor / M145) 3 0.7780
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7771
Abscisic acid receptor PYL10 Q8H1R0 PYL10_ARATH Arabidopsis thaliana 3 0.7765
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7764
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7750
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7731
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7712
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7699
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7661
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7645
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7625
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7614
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7613
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7610
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7600
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7599
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7598
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7595
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7568
Proto-oncogene tyrosine-protein kinase receptor Ret P07949 RET_HUMAN Homo sapiens 3 0.7566
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7560
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7541
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7533
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7504
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7502
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7474
Lactoperoxidase A0A452E9Y6 PERL_CAPHI Capra hircus 2 0.7471
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7470
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7457
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.7433
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7425
TGF-beta receptor type-1 P36897 TGFR1_HUMAN Homo sapiens 3 0.7424
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7408
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7373
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7359
cGMP-dependent protein kinase, putative A5K0N4 A5K0N4_PLAVS Plasmodium vivax 3 0.7355
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7355
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7350
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7349
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.7345
Putative snRNP Sm-like protein Q8ZYG5 Q8ZYG5_PYRAE Pyrobaculum aerophilum 2 0.7338
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7322
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7315
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7286
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7282
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7260
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7251
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7250
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7249
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7248
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 2 0.7243
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7240
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7227
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7220
Dipeptidyl peptidase 4 P22411 DPP4_PIG Sus scrofa 3 0.7194
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7194
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7187
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7178
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7177
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7174
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.7166
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7158
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 2 0.7158
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7157
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7156
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7153
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7153
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7143
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7130
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 2 0.7129
Casein kinase I isoform gamma-3 Q9Y6M4 KC1G3_HUMAN Homo sapiens 3 0.7113
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 2 0.7113
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7111
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7103
Enoyl-ACP reductase Q9BH77 Q9BH77_PLAFA Plasmodium falciparum 3 0.7099
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 2 0.7099
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7097
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7085
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7082
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7076
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7075
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7074
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7069
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7067
ADP compounds hydrolase NudE P45799 NUDE_ECOLI Escherichia coli 2 0.7062
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7051
Ephrin type-A receptor 3 P29320 EPHA3_HUMAN Homo sapiens 3 0.7037
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7031
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7017
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7014
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 2 0.7011
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 2 0.7003
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 3 0.7002

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