P-hydroxycinnamic acid, ethyl ester - Compound Card

P-hydroxycinnamic acid, ethyl ester

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P-hydroxycinnamic acid, ethyl ester

Structure
Zoomed Structure
  • Family: Animalia - Apidae
  • Kingdom: Animalia
  • Class: Ester
Canonical Smiles CCOC(=O)/C=C/c1ccc(cc1)O
InChI InChI=1S/C11H12O3/c1-2-14-11(13)8-5-9-3-6-10(12)7-4-9/h3-8,12H,2H2,1H3/b8-5+
InChIKey ZOQCEVXVQCPESC-VMPITWQZSA-N
Formula C11H12O3
HBA 3
HBD 1
MW 192.21
Rotatable Bonds 3
TPSA 46.53
LogP 1.97
Number Rings 1
Number Aromatic Rings 1
Heavy Atom Count 14
Formal Charge 0
Fraction CSP3 0.18
Exact Mass 192.08
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Apis species Apidae Animalia 7459

Showing of synonyms

  • Boutabet K, Kebsa W, et al. (2011). Polyphenolic fraction of Algerian propolis protects rat kidney against acute oxidative stress induced by doxorubicin. Indian Journal of Nephrology,2011,21(2),101-106. [View] [PubMed]
CPRiL: 101536
Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 192.21 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.47
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.17
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.5
Plasma Protein Binding
33.24
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
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.1
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
0.72
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.75
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.42
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Toxic
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
4.18
Rat (Acute)
1.97
Rat (Chronic Oral)
2.38
Fathead Minnow
4.17
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
308.16
Hydration Free Energy
-9.04
Log(D) at pH=7.4
2.22
Log(P)
2.74
Log S
-2.93
Log(Vapor Pressure)
-3.57
Melting Point
107.58
pKa Acid
9.84
pKa Basic
2.55
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.9359
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.9359
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9336
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.9336
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9015
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9015
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9000
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.9000
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8846
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8846
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8315
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8315
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8259
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8259
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8117
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8117
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8077
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.8077
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8057
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8057
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7956
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7956
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7939
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7939
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7876
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7876
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7829
Type IV / VI secretion system DotU domain-containing protein Q9KN50 Q9KN50_VIBCH Vibrio cholerae serotype O1 2 0.7829
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7818
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7818
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7740
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 2 0.7740
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7733
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7733
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7730
Cytochrome P450 3A4 P08684 CP3A4_HUMAN Homo sapiens 3 0.7730
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7689
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7689
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7671
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7671
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7667
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7667
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7512
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7512
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7508
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7508
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7506
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7506
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7448
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7448
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7441
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7441
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7398
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7398
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7376
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7376
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7335
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7335
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7328
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7328
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7326
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7326
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7318
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7318
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7281
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7281
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7273
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7273
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7265
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7265
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7258
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7258
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7241
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7241
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7214
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7214
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7212
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7212
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7211
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7211
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7206
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7206
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7206
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7206
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7188
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7188
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7171
Adenosine monophosphate-protein transferase Q8ZVF7 Q8ZVF7_PYRAE Pyrobaculum aerophilum 3 0.7171
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7156
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7156
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7147
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7147
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7137
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7137
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7127
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7127
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7125
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7125
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7110
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7110
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7105
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7105
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7101
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7101
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7095
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7095
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7095
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7095
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7092
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7092
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7086
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7086
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7086
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7086
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7075
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7075
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7065
Biotin carboxylase P43873 ACCC_HAEIN Haemophilus influenzae 2 0.7065
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7062
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7062
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7056
Cholesterol side-chain cleavage enzyme, mitochondrial P00189 CP11A_BOVIN Bos taurus 3 0.7056
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7055
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7055
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7051
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7051
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7051
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7051
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7050
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7050
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 2 0.7049
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 2 0.7049
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7049
Histone deacetylase-like amidohydrolase Q70I53 HDAH_ALCSD Alcaligenes sp.) 2 0.7049
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7046
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7046
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7046
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7046
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7045
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7045
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7037
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7037
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 2 0.7022
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 2 0.7022
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7019
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7019
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7013
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7013
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7012
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7012
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7012
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7012
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7012
Protein BRASSINOSTEROID INSENSITIVE 1 O22476 BRI1_ARATH Arabidopsis thaliana 3 0.7012
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7009
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7009
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7007
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7006
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7006
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7000
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7000

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