2-[penta-1,3-diyn-1-yl]-5-[3,4-dihydroxy-but-1-yn-1-yl] thiophene - Compound Card

2-[penta-1,3-diyn-1-yl]-5-[3,4-dihydroxy-but-1-yn-1-yl] thiophene

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2-[penta-1,3-diyn-1-yl]-5-[3,4-dihydroxy-but-1-yn-1-yl] thiophene

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Thiophene
Canonical Smiles CC#CC#Cc1ccc(s1)C#CC(CO)O
InChI InChI=1S/C13H10O2S/c1-2-3-4-5-12-8-9-13(16-12)7-6-11(15)10-14/h8-9,11,14-15H,10H2,1H3
InChIKey MZCFHXFKOQBSQU-UHFFFAOYSA-N
Formula C13H10O2S
HBA 3
HBD 2
MW 230.29
Rotatable Bonds 1
TPSA 40.46
LogP 0.83
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 16
Formal Charge 0
Fraction CSP3 0.23
Exact Mass 230.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Pluchea dioscoridis Asteraceae Plantae —
2 Sphaeranthus suaveolens Asteraceae Plantae 1548666

Showing of synonyms

  • Ahmed AA, Mahmoud AA (1997). Carvotacetone derivatives from the Egyptian plant Sphaeranthus suaveolens. Phytochemistry,1997,45(3),533-535. [View]
  • Bohlmann F, Metwally MA, et al. (1984). Eudesmanolides from Pluchea dioscoridis. Phytochemistry,1984,23(9),1975-1977. [View]
Pubchem: 25014552
Nmrshiftdb2: 70059453
Bindingdb: 50035708

No compound-protein relationship available.

Structure

SMILES: c1ccsc1

Level: 0

Mol. Weight: 230.29 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.17
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-3.82
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.13
Plasma Protein Binding
48.81
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.31
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.91
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.88
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
5.02
Rat (Acute)
2.56
Rat (Chronic Oral)
1.62
Fathead Minnow
4.61
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
350.68
Hydration Free Energy
-9.66
Log(D) at pH=7.4
2.86
Log(P)
2.92
Log S
-2.66
Log(Vapor Pressure)
-6.6
Melting Point
82.35
pKa Acid
9.28
pKa Basic
-0.84
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.9527
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.9527
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.9250
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.9250
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 3 0.9085
Cyclin-dependent kinase 8 P49336 CDK8_HUMAN Homo sapiens 3 0.9085
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.8885
Purine nucleoside phosphorylase Q8I3X4 Q8I3X4_PLAF7 Plasmodium falciparum 3 0.8885
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.8833
Amine oxidase [flavin-containing] B P27338 AOFB_HUMAN Homo sapiens 3 0.8833
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8793
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.8793
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8754
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8754
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.8720
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.8720
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8714
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8714
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8659
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.8659
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.8630
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.8630
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8614
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.8614
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8596
Quorum-sensing transcriptional activator Q8XBD0 Q8XBD0_ECO57 Escherichia coli O157:H7 3 0.8596
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8479
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8479
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8407
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8407
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8359
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8359
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8342
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8342
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8282
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.8282
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.8279
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.8279
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8241
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8241
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.8235
Disintegrin and metalloproteinase domain-containing protein 17 P78536 ADA17_HUMAN Homo sapiens 3 0.8235
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8164
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.8164
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8115
Purine nucleoside phosphorylase DeoD-type Q5EEL8 DEOD_BACCE Bacillus cereus 3 0.8115
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8077
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.8077
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8048
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.8048
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8040
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8040
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8014
Beta-glucosidase Q8T0W7 Q8T0W7_9NEOP Neotermes koshunensis 3 0.8014
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7970
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7970
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7961
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7961
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7849
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7849
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7813
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7813
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7785
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7785
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7769
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7769
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7701
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7701
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7658
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7658
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7650
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7650
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7647
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7647
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7622
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7622
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7618
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7618
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7595
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7595
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7590
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7590
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 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 0.7586
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7586
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7579
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7579
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7558
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7558
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7536
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7536
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7488
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7488
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7417
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7417
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7383
Collagenase 3 P45452 MMP13_HUMAN Homo sapiens 3 0.7383
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7377
HTH-type transcriptional regulator EthR P9WMC1 ETHR_MYCTU Mycobacterium tuberculosis 2 0.7377
Putative cysteine ligase BshC P55342 BSHC_BACSU Bacillus subtilis 3 0.7330
Putative cysteine ligase BshC P55342 BSHC_BACSU Bacillus subtilis 3 0.7330
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7309
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7309
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7306
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 2 0.7306
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7304
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7304
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7294
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7294
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7250
Tyrosine 3-monooxygenase P04177 TY3H_RAT Rattus norvegicus 3 0.7250
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7249
Plasma membrane ATPase Q42932 Q42932_NICPL Nicotiana plumbaginifolia 2 0.7249
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7241
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 2 0.7241
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7236
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7236
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7205
Adenosine kinase Q9TVW2 ADK_TOXGO Toxoplasma gondii 3 0.7205
2-keto-3-deoxy-gluconate kinase Q96XN9 Q96XN9_SULTO Sulfolobus tokodaii 3 0.7191
2-keto-3-deoxy-gluconate kinase Q96XN9 Q96XN9_SULTO Sulfolobus tokodaii 3 0.7191
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 2 0.7182
Fumarate reductase subunit D P0A8Q3 FRDD_ECOLI Escherichia coli 2 0.7182
Methionine--tRNA ligase P00959 SYM_ECOLI Escherichia coli 3 0.7175
Methionine--tRNA ligase P00959 SYM_ECOLI Escherichia coli 3 0.7175
Aminopeptidase A2V759 A2V759_9BACL Aneurinibacillus sp. AM-1 3 0.7170
Aminopeptidase A2V759 A2V759_9BACL Aneurinibacillus sp. AM-1 3 0.7170
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7162
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7162
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 2 0.7150
Epothilone C/D epoxidase Q9KIZ4 C167_SORCE Sorangium cellulosum 2 0.7150
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7100
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 2 0.7100
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7099
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 2 0.7099
Metallophosphoesterase MPPED2 B1WBP0 MPPD2_RAT Rattus norvegicus 3 0.7090
Metallophosphoesterase MPPED2 B1WBP0 MPPD2_RAT Rattus norvegicus 3 0.7090
Glutathione S-transferase Q8ILQ7 GST_PLAFA Plasmodium falciparum 3 0.7089
Glutathione S-transferase Q8ILQ7 GST_PLAFA Plasmodium falciparum 3 0.7089
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7063
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7063
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7062
Ribonuclease 4 P15468 RNAS4_PIG Sus scrofa 2 0.7062
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7060
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7060
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7060
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7060
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7055
Diamine acetyltransferase 1 P21673 SAT1_HUMAN Homo sapiens 2 0.7055
Tyrosine-protein kinase receptor TYRO3 P55144 TYRO3_MOUSE Mus musculus 3 0.7050
Tyrosine-protein kinase receptor TYRO3 P55144 TYRO3_MOUSE Mus musculus 3 0.7050
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7024
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7024
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7023
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7023
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7021
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 2 0.7021
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
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7004
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7004
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7002
Single-stranded-DNA-specific exonuclease RecJ D0EM60 D0EM60_DEIRD Deinococcus radiodurans 2 0.7002

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