4,5-di-p-trans-coumaroylquinic acid - Compound Card

4,5-di-p-trans-coumaroylquinic acid

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4,5-di-p-trans-coumaroylquinic acid

Structure
Zoomed Structure
  • Family: Plantae - Zygophyllaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Quinic Acid Derivative
Canonical Smiles Oc1ccc(cc1)/C=C/C(=O)O[C@@H]1[C@H](O)C[C@@](C[C@H]1OC(=O)/C=C/c1ccc(cc1)O)(O)C(=O)O
InChI InChI=1S/C25H24O10/c26-17-7-1-15(2-8-17)5-11-21(29)34-20-14-25(33,24(31)32)13-19(28)23(20)35-22(30)12-6-16-3-9-18(27)10-4-16/h1-12,19-20,23,26-28,33H,13-14H2,(H,31,32)/b11-5+,12-6+/t19-,20-,23-,25+/m1/s1
InChIKey NRDKGYVJVVIBTH-UZLNCMORSA-N
Formula C25H24O10
HBA 9
HBD 5
MW 484.46
Rotatable Bonds 7
TPSA 170.82
LogP 1.62
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 484.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tribulus terrestris Zygophyllaceae Plantae 210369

Showing of synonyms

  • Hammoda HM, Ghazy NM, et al. (2013). Chemical constituents from Tribulus terrestris and screening of their antioxidant activity. Phytochemistry,2013,92,153-159. [View] [PubMed]
Pubchem: 44715686
Chebi: 194119
Nmrshiftdb2: 70003038
CPRiL: 62669
Structure

SMILES: c1ccccc1C=CC(=O)OC2C(CCCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 484.46 g/mol

Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 484.46 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 484.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 484.46 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.54
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.260
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-3.89

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.840
Plasma Protein Binding
72.88
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
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
Non-Substrate
OATP1B1
Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
12.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.040
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.330
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.960
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-213.150
Rat (Acute)
2.230
Rat (Chronic Oral)
3.600
Fathead Minnow
4.110
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
539.560
Hydration Free Energy
-3.010
Log(D) at pH=7.4
-0.170
Log(P)
2.49
Log S
-2.92
Log(Vapor Pressure)
-13.43
Melting Point
248.98
pKa Acid
4.12
pKa Basic
5.81
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8929
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8929
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8907
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.8907
Bis(5'-adenosyl)-triphosphatase P49789 FHIT_HUMAN Homo sapiens 3 0.8849
Bis(5'-adenosyl)-triphosphatase P49789 FHIT_HUMAN Homo sapiens 3 0.8849
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8746
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8746
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8176
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.8176
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8102
Coagulation factor X P00742 FA10_HUMAN Homo sapiens 3 0.8102
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8084
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8084
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8024
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.8024
Copper-transporting ATPase Q97UU7 Q97UU7_SACS2 Saccharolobus solfataricus 4 0.7998
Copper-transporting ATPase Q97UU7 Q97UU7_SACS2 Saccharolobus solfataricus 4 0.7998
2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI Escherichia coli 3 0.7985
2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI Escherichia coli 3 0.7985
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7976
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7976
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7930
Chaperone protein HtpG P0A6Z3 HTPG_ECOLI Escherichia coli 3 0.7930
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7929
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7929
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7786
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7786
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7683
Squalene synthase P37268 FDFT_HUMAN Homo sapiens 4 0.7683
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7663
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7663
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7648
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7648
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7636
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 3 0.7636
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7616
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7616
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7554
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7554
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7513
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7490
Activated CDC42 kinase 1 Q07912 ACK1_HUMAN Homo sapiens 3 0.7490
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7481
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7481
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7475
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7475
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7432
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7432
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7424
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7424
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7408
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7408
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7401
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7401
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7399
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7399
Orf1ab polyprotein Q6T1E9 Q6T1E9_CVHSA SARS coronavirus CUHK-L2 3 0.7381
Orf1ab polyprotein Q6T1E9 Q6T1E9_CVHSA SARS coronavirus CUHK-L2 3 0.7381
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7371
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7371
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7357
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7357
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7326
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 2 0.7326
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7287
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7287
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7283
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7283
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7277
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7277
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7262
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7262
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7259
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7259
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7257
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7257
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7254
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7254
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase Q81LL4 MTNN_BACAN Bacillus anthracis 2 0.7254
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7254
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 3 0.7254
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7254
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7236
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7236
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7210
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7210
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7209
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7209
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7206
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7206
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7204
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7204
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7200
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7200
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7195
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7195
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7185
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7185
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7184
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7184
Ribosomal protein S6 kinase alpha-1 Q15418 KS6A1_HUMAN Homo sapiens 3 0.7175
Ribosomal protein S6 kinase alpha-1 Q15418 KS6A1_HUMAN Homo sapiens 3 0.7175
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7154
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7154
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7147
RIO-type serine/threonine-protein kinase Rio1 O28471 RIO1_ARCFU Archaeoglobus fulgidus 2 0.7147
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7145
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7145
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7136
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7136
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7118
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7118
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7098
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7098
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7095
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 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
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7091
Protein kinase C iota type Q62074 KPCI_MOUSE Mus musculus 2 0.7091
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7084
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 2 0.7084
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7074
Genome polyprotein C0LMU0 C0LMU0_9FLAV dengue virus type 3 3 0.7074
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7071
Myosin heavy chain kinase A P42527 MHCKA_DICDI Dictyostelium discoideum 2 0.7071
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7062
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7062
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7060
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7060
Anthranilate phosphoribosyltransferase P00500 TRPD_ACIAD Acinetobacter baylyi 2 0.7060
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7060
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7055
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7055
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7047
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7047
Nucleoside diphosphate kinase Q5SLV5 NDK_THET8 Thermus thermophilus 2 0.7042
Nucleoside diphosphate kinase Q5SLV5 NDK_THET8 Thermus thermophilus 2 0.7042
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7040
Urokinase-type plasminogen activator P00749 UROK_HUMAN Homo sapiens 2 0.7040
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7035
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7035
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7034
Antitumor antibiotic C-1027 apoprotein Q06110 CAGA_STRGL Streptomyces globisporus 3 0.7034
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7025
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7025
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7019
Fructose-1,6-bisphosphatase 1 P09467 F16P1_HUMAN Homo sapiens 2 0.7019
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7019
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 2 0.7019
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7017
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7017
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7012
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7012
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7011
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7011
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7010
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 2 0.7010
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7007
Chemotaxis protein CheA Q56310 CHEA_THEMA Thermotoga maritima 3 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 2 0.7007
Chemotaxis protein CheA Q56310 CHEA_THEMA Thermotoga maritima 3 0.7007
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7007

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