Toussaintine F - Compound Card

Toussaintine F

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Toussaintine F

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-/m1/s1
InChIKey GENLFYMJWHMPJH-CXLXYXDYSA-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)
-4.71
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
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.450
Plasma Protein Binding
50.34
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
2.510
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.820
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
5.790
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
-2.440
Rat (Acute)
3.100
Rat (Chronic Oral)
2.680
Fathead Minnow
4.080
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
402.660
Hydration Free Energy
-11.900
Log(D) at pH=7.4
1.090
Log(P)
1.35
Log S
-2.19
Log(Vapor Pressure)
-7.45
Melting Point
143.78
pKa Acid
8.14
pKa Basic
5.08
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9557
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9557
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.9063
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.9063
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8883
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8883
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8620
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8620
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8508
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8508
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8404
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.8404
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8318
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8318
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7821
Actin, alpha skeletal muscle P68135 ACTS_RABIT Oryctolagus cuniculus 3 0.7821
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7789
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7789
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7732
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7732
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7721
NAD(P) transhydrogenase subunit alpha part 1 Q2RSB2 PNTAA_RHORT Rhodospirillum rubrum 3 0.7721
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7681
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7681
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7596
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7596
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7560
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7560
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7524
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7524
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7500
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7500
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7409
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7409
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7306
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7306
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7304
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7304
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7301
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7301
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7285
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 3 0.7285
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7262
F420-dependent methylenetetrahydromethanopterin dehydrogenase P94951 MTD_METKA Methanopyrus kandleri 2 0.7262
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7256
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7256
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7252
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7252
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7231
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7231
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7188
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 3 0.7188
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7164
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 2 0.7164
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7164
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7164
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7133
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7133
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7130
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7130
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7129
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7129
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7127
Indole-3-glycerol phosphate synthase P9WFX7 TRPC_MYCTU Mycobacterium tuberculosis 2 0.7127
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7119
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7119
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7093
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7093
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7068
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7068
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7064
Polymerase basic protein 2 P31345 PB2_I75A3 Influenza A virus 2 0.7064
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 2 0.7061
Beta-galactoside-specific lectin 1 P81446 ML1_VISAL Viscum album 2 0.7061
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7042
Type II methyltransferase M.RsrI P14751 MTR1_RHOSH Cereibacter sphaeroides 3 0.7042
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7024
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7024
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7018
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7018
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7015
AcsD Q93AT8 Q93AT8_DICCH Dickeya chrysanthemi 3 0.7015

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