N-isobutyl-6- 2-thienyl -2E,4E-hexadienamide - Compound Card

N-isobutyl-6- 2-thienyl -2E,4E-hexadienamide

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N-isobutyl-6- 2-thienyl -2E,4E-hexadienamide

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Amide
Canonical Smiles CC(CNC(=O)/C=C/C=C/Cc1cccs1)C
InChI InChI=1S/C14H19NOS/c1-12(2)11-15-14(16)9-5-3-4-7-13-8-6-10-17-13/h3-6,8-10,12H,7,11H2,1-2H3,(H,15,16)/b4-3+,9-5+
InChIKey KNGBXFMEGLRFHV-PRKJJMSOSA-N
Formula C14H19NOS
HBA 2
HBD 1
MW 249.38
Rotatable Bonds 6
TPSA 29.1
LogP 3.18
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 17
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 249.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chrysanthemum morifolium Asteraceae Plantae 41568
2 Matricaria pubescens Asteraceae Plantae 99022

Showing of synonyms

  • Shahat AA, Apers S, et al. (2001). Isolation and complete NMR assignment of the numbing principle from Chrysanthemum morifolium. Fitoterapia,2001,72,89-91. [View] [PubMed]
  • Greger H, Hofer O (1984). On the pungent principle of Matricaria pubescens. Phytochemistry,1984,23(5),1173-1174. [View]
Pubchem: 14776997
Nmrshiftdb2: 60075053

No compound-protein relationship available.

Structure

SMILES: c1ccsc1

Level: 0

Mol. Weight: 249.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.42
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.86
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.7

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.96
Plasma Protein Binding
52.78
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
3.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.7
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.92
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
4.85
Rat (Acute)
2.31
Rat (Chronic Oral)
1.67
Fathead Minnow
4.78
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
320.72
Hydration Free Energy
-9.24
Log(D) at pH=7.4
3.03
Log(P)
3.61
Log S
-3.56
Log(Vapor Pressure)
-5.12
Melting Point
92.21
pKa Acid
10.39
pKa Basic
4.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9782
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9782
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.9118
Prolyl endopeptidase P23687 PPCE_PIG Sus scrofa 3 0.9118
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8439
ADP-ribosylation factor 1 P84077 ARF1_HUMAN Homo sapiens 2 0.8439
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8323
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.8323
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.8234
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.8234
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8007
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8007
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7750
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7750
Avd protein A7YYL1 A7YYL1_XENTR Xenopus tropicalis 3 0.7713
Avd protein A7YYL1 A7YYL1_XENTR Xenopus tropicalis 3 0.7713
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7706
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7706
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7705
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7705
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7692
prolyl oligopeptidase Q9X6R4 Q9X6R4_AERCA Aeromonas caviae 2 0.7692
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7611
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 2 0.7611
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7601
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 2 0.7601
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7547
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7547
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7538
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7538
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7481
Alpha/beta hydrolase fold protein D2J2T6 D2J2T6_9RHIZ Ochrobactrum sp. T63 3 0.7481
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7480
Sodium-dependent dopamine transporter Q7K4Y6 DAT_DROME Drosophila melanogaster 2 0.7480
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7474
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7474
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7454
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7454
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7443
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 2 0.7443
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7432
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7432
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7381
Dipeptidyl peptidase 4 P14740 DPP4_RAT Rattus norvegicus 2 0.7381
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7343
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7343
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7340
ADP-ribosylation factor 1 P84080 ARF1_BOVIN Bos taurus 2 0.7340
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7323
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 2 0.7323
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7316
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 2 0.7316
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7295
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7295
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7287
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7287
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7279
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 2 0.7279
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7271
Chorismate mutase AroH P19080 AROH_BACSU Bacillus subtilis 2 0.7271
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7250
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 2 0.7250
Protein claret segregational P20480 NCD_DROME Drosophila melanogaster 2 0.7243
Protein claret segregational P20480 NCD_DROME Drosophila melanogaster 2 0.7243
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7231
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7231
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7228
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7228
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7221
Prolyl tripeptidyl peptidase Q7MUW6 PTP_PORGI Porphyromonas gingivalis 2 0.7221
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7208
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7208
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7195
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7195
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7181
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7181
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7171
Cytochrome P450 Q93H81 Q93H81_STRAX Streptomyces avermitilis 2 0.7171
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7159
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 2 0.7159
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7158
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7158
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7123
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 2 0.7123
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7120
Transcriptional activator, LuxR/UhpA family of regulators Q7NQP7 Q7NQP7_CHRVO Chromobacterium violaceum 2 0.7120
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7114
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7114
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7104
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 2 0.7104
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7089
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7089
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 2 0.7082
N-acyl-aromatic-L-amino acid amidohydrolase (carboxylate-forming) Q91XE4 ACY3_MOUSE Mus musculus 2 0.7082
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7076
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7076
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7065
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7065
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7057
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7057
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7053
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7053
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 2 0.7042
Carboxypeptidase A1 P00730 CBPA1_BOVIN Bos taurus 2 0.7042
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7028
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 2 0.7028
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7021
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7021

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