2-chloro-4-(5-(penta-1,3-diynyl)thiophen-2-yl)but-3-yn-1-ol - Compound Card

2-chloro-4-(5-(penta-1,3-diynyl)thiophen-2-yl)but-3-yn-1-ol

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2-chloro-4-(5-(penta-1,3-diynyl)thiophen-2-yl)but-3-yn-1-ol

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Alkyne
Canonical Smiles CC#CC#Cc1ccc(s1)C#CC(CO)Cl
InChI InChI=1S/C13H9ClOS/c1-2-3-4-5-12-8-9-13(16-12)7-6-11(14)10-15/h8-9,11,15H,10H2,1H3
InChIKey OIMRGFPTZIUKNX-UHFFFAOYSA-N
Formula C13H9ClOS
HBA 2
HBD 1
MW 248.73
Rotatable Bonds 1
TPSA 20.23
LogP 2.07
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 248.01
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —

Showing of synonyms

  • Dawidar AA, Metwally M (1985). New alpha-cyclocostunolide and isocostic acid derivatives from Pluchea dioscoridis. Chemical and Pharmaceutical Bulletin,1985,33(11),5068-5070. [View]
Pubchem: 14550069

No compound-protein relationship available.

Structure

SMILES: c1ccsc1

Level: 0

Mol. Weight: 248.73 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.45
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.53
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.32

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.17
Plasma Protein Binding
51.61
Steady State Volume of Distribution
-

Metabolism

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

Excretion

Clearance
8.69
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.8
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.67
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.05
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
Toxic
T. Pyriformis
6.01
Rat (Acute)
2.59
Rat (Chronic Oral)
1.13
Fathead Minnow
4.81
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
343.47
Hydration Free Energy
-6.41
Log(D) at pH=7.4
3.58
Log(P)
4.09
Log S
-3.84
Log(Vapor Pressure)
-5.16
Melting Point
68.42
pKa Acid
9.6
pKa Basic
-1.68
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.8549
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.8549
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8116
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8116
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.8078
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.8078
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8067
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8067
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.8008
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.8008
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7850
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7850
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 2 0.7783
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 2 0.7783
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7699
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7699
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7688
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7688
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 2 0.7668
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 2 0.7668
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7665
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7665
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7660
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7660
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7588
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7588
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7588
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7588
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7554
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7554
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7495
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7495
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7494
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7494
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7482
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 2 0.7482
Cytokinin dehydrogenase 1 Q9T0N8 CKX1_MAIZE Zea mays 3 0.7476
Cytokinin dehydrogenase 1 Q9T0N8 CKX1_MAIZE Zea mays 3 0.7476
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 2 0.7469
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 2 0.7469
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7416
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 2 0.7416
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7399
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7399
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7382
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7382
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7361
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7361
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7354
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7354
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7352
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7352
Protein UshA P07024 USHA_ECOLI Escherichia coli 2 0.7349
Protein UshA P07024 USHA_ECOLI Escherichia coli 2 0.7349
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 2 0.7332
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 2 0.7332
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7316
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7316
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7308
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7308
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7304
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7304
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7302
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 2 0.7302
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7282
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7282
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7270
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7270
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7269
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7269
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7257
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7257
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7251
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7251
Protein claret segregational P20480 NCD_DROME Drosophila melanogaster 2 0.7247
Protein claret segregational P20480 NCD_DROME Drosophila melanogaster 2 0.7247
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7243
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7243
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7238
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7238
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7238
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 2 0.7238
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 2 0.7227
Metallophosphoesterase A3DJ38 A3DJ38_HUNT2 Clostridium thermocellum 2 0.7227
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7226
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7226
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7221
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 2 0.7221
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7213
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 2 0.7213
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7211
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7211
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 2 0.7201
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 2 0.7201
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3 Q16875 F263_HUMAN Homo sapiens 2 0.7199
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 3 Q16875 F263_HUMAN Homo sapiens 2 0.7199
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7197
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7197
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7191
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 2 0.7191
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 2 0.7191
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7191
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 2 0.7183
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 2 0.7183
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7176
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7176
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7172
Nucleoside 2-deoxyribosyltransferase Q8RLY5 Q8RLY5_LACHE Lactobacillus helveticus 2 0.7172
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7169
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 2 0.7169
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7163
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 2 0.7163
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7152
GMP reductase Q81JJ9 GUAC_BACAN Bacillus anthracis 2 0.7152
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7146
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7146
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7145
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7145
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7142
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7142
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7124
Abscisic acid receptor PYL2 O80992 PYL2_ARATH Arabidopsis thaliana 2 0.7124
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7120
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 2 0.7120
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7115
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7115
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 2 0.7109
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 2 0.7109
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7081
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 2 0.7081
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7072
cGMP-dependent protein kinase 1 Q13976 KGP1_HUMAN Homo sapiens 2 0.7072
Cytokinin dehydrogenase 1 Q9T0N8 CKX1_MAIZE Zea mays 2 0.7066
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7066
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 2 0.7066
Cytokinin dehydrogenase 1 Q9T0N8 CKX1_MAIZE Zea mays 2 0.7066
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7061
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7061
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7060
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7060
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7052
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7052
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7049
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7049
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7043
Lanosterol 14-alpha demethylase CYP51 P10614 CP51_YEAST Saccharomyces cerevisiae 3 0.7043
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7040
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 2 0.7040
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7029
Abscisic acid receptor PYL9 Q84MC7 PYL9_ARATH Arabidopsis thaliana 2 0.7029
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7025
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7025
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7023
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 2 0.7023
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 2 0.7022
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 2 0.7022
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7020
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7020
Gamma-aminobutyric acid type B receptor subunit 1 Q9UBS5 GABR1_HUMAN Homo sapiens 2 0.7019
Gamma-aminobutyric acid type B receptor subunit 1 Q9UBS5 GABR1_HUMAN Homo sapiens 2 0.7019
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7014
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7014
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7009
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7009
Nucleoside diphosphate kinase A5J299 A5J299_PENVA Penaeus vannamei 2 0.7006
Nucleoside diphosphate kinase A5J299 A5J299_PENVA Penaeus vannamei 2 0.7006
S-methyl-5'-thioadenosine phosphorylase Q97W94 MTAP_SACS2 Saccharolobus solfataricus 2 0.7002
S-methyl-5'-thioadenosine phosphorylase Q97W94 MTAP_SACS2 Saccharolobus solfataricus 2 0.7002

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