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5-p-trans-coumaroylquinic acid
- Family: Plantae - Asteraceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Quinic Acid Derivative
| Canonical Smiles | O=C(O[C@@H]1C[C@@](O)(C[C@H]([C@H]1O)O)C(=O)O)/C=C/c1ccc(cc1)O |
|---|---|
| InChI | InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(19)24-12-8-16(23,15(21)22)7-11(18)14(12)20/h1-6,11-12,14,17-18,20,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14-,16+/m1/s1 |
| InChIKey | BMRSEYFENKXDIS-OTCYKTEZSA-N |
| Formula | C16H18O8 |
| HBA | 7 |
| HBD | 5 |
| MW | 338.31 |
| Rotatable Bonds | 4 |
| TPSA | 144.52 |
| LogP | -0.35 |
| Number Rings | 2 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 24 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.38 |
| Exact Mass | 338.1 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tribulus terrestris | Zygophyllaceae | Plantae | 210369 |
| 2 | Cynara cardunculus | Asteraceae | Plantae | 4265 |
Showing of synonyms
5-p-trans-coumaroylquinic acid
5746-55-4
Trans-5-O-(4-coumaroyl)-D-quinic acid
2-Coumaroylquinic acid
5-p-coumaroylquinic acid
1899-30-5
(1R,3S,4R,5S)-1,3,4-TRIHYDROXY-5-[(E)-3-(4-HYDROXYPHENYL)PROP-2-ENOYL]OXY-CYCLOHEXANE-1-CARBOXYLIC ACID
3-p-coumaroylquinic acid
5-O-(E)-p-Coumaroylquinic acid
P-Coumaroyl quinic acid
O-Coumaroylquinic acid
(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
CHEBI:15937
4C4BU5688G
3-O-p-Coumaroylquinic acid
(1S,3R,4R,5R)-1,3,4-Trihydroxy-5-(((E)-3-(4-hydroxyphenyl)acryloyl)oxy)cyclohexanecarboxylic acid
(1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(2E)-3-(4-hydroxyphenyl)prop-2-enoyloxy]cyclohexanecarboxylic acid
P-Coumaroylquinic acid
UNII-4C4BU5688G
Coumaroylquinic acid
5-P-COQA
CHEMBL284243
SCHEMBL10307372
CHEBI:75500
HY-N10543A
HY-N10543
FC71593
5-P-COUMAROYLQUINIC ACID, (E)-
Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-((3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (1S-(1alpha,3alpha,4alpha,5beta))-
DA-59466
DA-70005
PD210271
TS-10189
21600YP321
CS-0610713
CS-0895414
TRANS-P-COUMARIC ACID 5-O-D-QUINATE
H38724
Q27098307
(1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}cyclohexanecarboxylic acid
CINNAMIC ACID, P-HYDROXY-, 5-ESTER WITH 1,3,4,5-TETRAHYDROXYCYCLOHEXANECARBOXYLIC ACID, (E)-
CYCLOHEXANECARBOXYLIC ACID, 1,3,4-TRIHYDROXY-5-(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-, (1S,3R,4R,5R)-
CYCLOHEXANECARBOXYLIC ACID, 1,3,4-TRIHYDROXY-5-(((2E)-3-(4-HYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (1S,3R,4R,5R)-
CYCLOHEXANECARBOXYLIC ACID, 1,3,4-TRIHYDROXY-5-((3-(4-HYDROXYPHENYL)-1-OXO-2-PROPENYL)OXY)-, (1S-(1.ALPHA.,3.ALPHA.,4.ALPHA.,5.BETA.(E)))-
Cyclohexanecarboxylic acid, 1,3,4-trihydroxy-5-((3-(4-hydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (1S-(1alpha,3alpha,4alpha,5beta(E)))-
- 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]
- Farag MA, El-Ahmady SH, et al. (2013). Metabolomics driven analysis of artichoke leaf and its commercial products via UHPLC–q-TOF-MS and chemometrics. Phytochemistry,2013,95,177-187. [View] [PubMed]
Pubchem:
6441280
Cas:
5746-55-4
Zinc:
ZINC000003804525
Kegg Ligand:
C12208
Chebi:
15937
Nmrshiftdb2:
60028591
Metabolights:
MTBLC15937
Chembl:
CHEMBL284243
No compound-protein relationship available.
SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 338.31 g/mol
SMILES: C1CCCCC1
Level: 0
Mol. Weight: 338.31 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 338.31 g/mol
Antioxidant
Absorption
- Caco-2 (logPapp)
- -6.31
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.7
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -2.82
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.74
- Plasma Protein Binding
- 60.23
- 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
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 4.86
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.93
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.64
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 3.78
- 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
- -0.4
- Rat (Acute)
- 1.98
- Rat (Chronic Oral)
- 3.09
- Fathead Minnow
- 3.87
- 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
- 416.96
- Hydration Free Energy
- -10.31
- Log(D) at pH=7.4
- -1.16
- Log(P)
- -0.13
- Log S
- -1.55
- Log(Vapor Pressure)
- -12.57
- Melting Point
- 202.78
- pKa Acid
- 3.0
- pKa Basic
- 6.62
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.9299 |
| Albumin | P02768 | ALBU_HUMAN | Homo sapiens | 3 | 0.9299 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.9150 |
| Dihydrofolate reductase | P00378 | DYR_CHICK | Gallus gallus | 3 | 0.9150 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.8927 |
| Kinesin-like protein KIF11 | P52732 | KIF11_HUMAN | Homo sapiens | 3 | 0.8927 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.8413 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.8413 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8225 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8225 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8090 |
| Thymidylate synthase | P0A884 | TYSY_ECOLI | Escherichia coli | 2 | 0.8090 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7917 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7917 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7805 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7805 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 5 | 0.7646 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 5 | 0.7646 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7562 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7562 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7511 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7511 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7511 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7511 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7464 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7464 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7446 |
| Ephrin type-A receptor 2 | P29317 | EPHA2_HUMAN | Homo sapiens | 3 | 0.7446 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7444 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.7444 |
| 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 | 0.7399 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7399 |
| 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 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7333 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 2 | 0.7333 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.7309 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.7309 |
| Nucleoside diphosphate kinase | Q5SLV5 | NDK_THET8 | Thermus thermophilus | 2 | 0.7305 |
| Nucleoside diphosphate kinase | Q5SLV5 | NDK_THET8 | Thermus thermophilus | 2 | 0.7305 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7283 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 2 | 0.7283 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7278 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7278 |
| 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 |
| Activated CDC42 kinase 1 | Q07912 | ACK1_HUMAN | Homo sapiens | 3 | 0.7246 |
| Activated CDC42 kinase 1 | Q07912 | ACK1_HUMAN | Homo sapiens | 3 | 0.7246 |
| Biotin carboxylase | P43873 | ACCC_HAEIN | Haemophilus influenzae | 3 | 0.7243 |
| Biotin carboxylase | P43873 | ACCC_HAEIN | Haemophilus influenzae | 3 | 0.7243 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7209 |
| Capsid protein | Q9WBP8 | Q9WBP8_9VIRU | Adeno-associated virus - 1 | 2 | 0.7209 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.7206 |
| ABC-type polar amino acid transport system, ATPase component | Q8RCC2 | Q8RCC2_CALS4 | Caldanaerobacter subterraneus subsp. tengcongensis | 3 | 0.7206 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7205 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7205 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7198 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7198 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7186 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7186 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7174 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 2 | 0.7174 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7155 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7155 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7132 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7132 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7131 |
| Myosin heavy chain kinase A | P42527 | MHCKA_DICDI | Dictyostelium discoideum | 2 | 0.7131 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7093 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7093 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7074 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7074 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7063 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7063 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7061 |
| Anthranilate phosphoribosyltransferase | P00500 | TRPD_ACIAD | Acinetobacter baylyi | 2 | 0.7061 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7058 |
| Fructose-1,6-bisphosphatase 1 | P09467 | F16P1_HUMAN | Homo sapiens | 2 | 0.7058 |
| Mitogen-activated protein kinase kinase kinase 21 | Q5TCX8 | M3K21_HUMAN | Homo sapiens | 3 | 0.7052 |
| Mitogen-activated protein kinase kinase kinase 21 | Q5TCX8 | M3K21_HUMAN | Homo sapiens | 3 | 0.7052 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7049 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7049 |
| Purine nucleoside phosphorylase DeoD-type | B1JL34 | DEOD_YERPY | Yersinia pseudotuberculosis serotype O:3 | 2 | 0.7049 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7049 |
| Protein kinase C iota type | Q62074 | KPCI_MOUSE | Mus musculus | 2 | 0.7048 |
| Protein kinase C iota type | Q62074 | KPCI_MOUSE | Mus musculus | 2 | 0.7048 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7045 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7045 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7044 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7044 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7042 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7042 |
| Kynurenine--oxoglutarate transaminase 1 | Q16773 | KAT1_HUMAN | Homo sapiens | 2 | 0.7018 |
| Kynurenine--oxoglutarate transaminase 1 | Q16773 | KAT1_HUMAN | Homo sapiens | 2 | 0.7018 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7015 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 2 | 0.7015 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7014 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 2 | 0.7014 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7013 |
| Serine/threonine-protein kinase Chk2 | O96017 | CHK2_HUMAN | Homo sapiens | 2 | 0.7013 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7010 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 2 | 0.7010 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7006 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 2 | 0.7006 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7006 |
| Formate--tetrahydrofolate ligase | P21164 | FTHS_MOOTH | Moorella thermoacetica | 2 | 0.7006 |