3,5-di-O-caffeoylquinic acid - Compound Card

3,5-di-O-caffeoylquinic acid

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3,5-di-O-caffeoylquinic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles O=C(OC1CC(O)(CC(C1O)OC(=O)/C=C/c1ccc(c(c1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+
InChIKey KRZBCHWVBQOTNZ-FCXRPNKRSA-N
Formula C25H24O12
HBA 11
HBD 7
MW 516.46
Rotatable Bonds 7
TPSA 211.28
LogP 1.03
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 37
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 516.13
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Cynara cardunculus Asteraceae Plantae 4265

Showing of synonyms

  • 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: 13604687
Nmrshiftdb2: 60028434
Bindingdb: 50528375
CPRiL: 84372
Structure

SMILES: c1ccccc1C=CC(=O)OC2CC(CCC2)OC(=O)C=Cc3ccccc3

Level: 2

Mol. Weight: 516.46 g/mol

Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 516.46 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 516.46 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 516.46 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.67
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.87
Plasma Protein Binding
13.77
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
11.21
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.15
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.73
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.16
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
-462.15
Rat (Acute)
2.16
Rat (Chronic Oral)
3.82
Fathead Minnow
4.3
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
595.98
Hydration Free Energy
-2.97
Log(D) at pH=7.4
0.19
Log(P)
1.34
Log S
-2.73
Log(Vapor Pressure)
-13.75
Melting Point
241.62
pKa Acid
4.95
pKa Basic
5.89
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9345
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9345
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.9270
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 3 0.9270
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9076
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9076
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9040
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9040
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8697
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8697
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8672
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8672
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8633
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8633
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.8499
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.8499
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8419
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8419
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8347
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8347
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8317
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8317
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8273
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8273
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8187
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.8187
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8134
Formate--tetrahydrofolate ligase P21164 FTHS_MOOTH Moorella thermoacetica 3 0.8134
Ectonucleoside triphosphate diphosphohydrolase I Q5ZUA2 Q5ZUA2_LEGPH Legionella pneumophila subsp. pneumophila 3 0.8122
Ectonucleoside triphosphate diphosphohydrolase I Q5ZUA2 Q5ZUA2_LEGPH Legionella pneumophila subsp. pneumophila 3 0.8122
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7978
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7978
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7968
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7968
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7928
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7928
Nitrate reductase [NADH] 1 P17571 NIA1_MAIZE Zea mays 3 0.7902
Nitrate reductase [NADH] 1 P17571 NIA1_MAIZE Zea mays 3 0.7902
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7876
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7876
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7826
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7826
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7791
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7791
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7683
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7683
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7677
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7677
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7660
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7660
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7613
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7613
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7603
Putative choline kinase Q5CUP2 Q5CUP2_CRYPI Cryptosporidium parvum 3 0.7603
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7555
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7555
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 3 0.7521
Amino-acid acetyltransferase Q5FAK7 Q5FAK7_NEIG1 Neisseria gonorrhoeae 3 0.7521
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7505
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7505
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7499
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7499
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7492
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7492
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7483
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7483
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7398
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7398
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7374
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7374
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7374
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7374
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7359
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7359
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7343
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7343
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7338
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7338
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7303
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7303
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7264
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7264
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7191
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7191
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7181
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7181
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7176
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7176
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7167
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7167
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7165
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7165
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7157
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7157
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7149
Serine/threonine-protein kinase Chk2 O96017 CHK2_HUMAN Homo sapiens 2 0.7149
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7145
Tryptophan--tRNA ligase Q9PIB4 SYW_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 4 0.7145
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7141
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7141
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7136
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7136
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7134
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7134
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7134
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7134
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7129
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7129
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7127
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7127
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7109
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7109
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7102
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7102
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7077
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7077
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7075
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7075
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7063
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7063
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7061
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7061
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7057
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7057
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7044
DNA ligase P43813 DNLJ_HAEIN Haemophilus influenzae 3 0.7044
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7043
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7043
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7029
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7029
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7002
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7002
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 4 0.7002
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 4 0.7002
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7001
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7001

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