Toussaintine G - Compound Card

Toussaintine G

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Toussaintine G

Structure
Zoomed Structure
  • Family: Plantae - Annonaceae
  • Kingdom: Plantae
  • Class: N-Cinnamoyltetraketide
Canonical Smiles CO[C@H]1CC(=O)CC([C@]1(O)CC(=O)OC)NC(=O)/C=C/c1ccccc1
InChI InChI=1S/C19H23NO6/c1-25-16-11-14(21)10-15(19(16,24)12-18(23)26-2)20-17(22)9-8-13-6-4-3-5-7-13/h3-9,15-16,24H,10-12H2,1-2H3,(H,20,22)/b9-8+/t15?,16-,19+/m0/s1
InChIKey GENLFYMJWHMPJH-BXRZTHIPSA-N
Formula C19H23NO6
HBA 6
HBD 2
MW 361.39
Rotatable Bonds 6
TPSA 101.93
LogP 0.86
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.42
Exact Mass 361.15
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Toussaintia orientalis Annonaceae Plantae 489350

Showing of synonyms

  • Nyandoro SS, Ndanu J, et al. (2015). N-Cinnamoyltetraketide derivatives from the leaves of Toussaintia orientalis. Journal of Natural Products,2015,78(8),2045-2050. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: C1CCC(CC1=O)NC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 361.39 g/mol

Structure

SMILES: O=C1CCCCC1

Level: 0

Mol. Weight: 361.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 361.39 g/mol

Antimycobacterial

Absorption

Caco-2 (logPapp)
-4.79
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.580
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.39

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.450
Plasma Protein Binding
50.88
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
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
2.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.810
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.000
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.780
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
-2.560
Rat (Acute)
3.110
Rat (Chronic Oral)
2.690
Fathead Minnow
4.070
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
403.220
Hydration Free Energy
-11.940
Log(D) at pH=7.4
1.050
Log(P)
1.33
Log S
-2.18
Log(Vapor Pressure)
-7.46
Melting Point
142.32
pKa Acid
8.14
pKa Basic
5.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9588
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.9588
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9504
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9504
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9038
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.9038
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8706
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8706
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8686
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8686
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8094
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.8094
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8017
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8017
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7987
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.7987
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7820
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7820
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7772
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7772
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7731
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7731
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7689
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7689
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7585
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7585
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7526
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7526
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7525
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7525
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7503
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7503
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7482
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7482
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7452
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7452
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7428
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7428
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7339
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7339
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7323
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7323
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7316
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7316
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7314
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7314
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7272
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7272
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7212
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7212
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7207
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7207
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7199
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7199
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7141
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7141
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7106
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7106
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7078
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7078
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7077
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7077
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7073
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7073
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 4 0.7057
Iota toxin component Ia Q46220 Q46220_CLOPF Clostridium perfringens 4 0.7057
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7050
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7050
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 4 0.7039
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 4 0.7039
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7009
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7009
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7001
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7001

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