1-O-caffeoylquinic acid - Compound Card

1-O-caffeoylquinic acid

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1-O-caffeoylquinic acid

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles O=C(OC1(CC(O)C(C(C1)O)O)C(=O)O)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(21)25-16(15(23)24)6-11(19)14(22)12(20)7-16/h1-5,11-12,14,17-20,22H,6-7H2,(H,23,24)/b4-2+
InChIKey GWTUHAXUUFROTF-DUXPYHPUSA-N
Formula C16H18O9
HBA 8
HBD 6
MW 354.31
Rotatable Bonds 4
TPSA 164.75
LogP -0.65
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 25
Formal Charge 0
Fraction CSP3 0.38
Exact Mass 354.1
Number of Lipinski Rule Violations 1
# 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: 6451212
Nmrshiftdb2: 70019510
CPRiL: 416950
Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 354.31 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 354.31 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 354.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.41
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.13
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-3.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.69
Plasma Protein Binding
23.15
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
9.41
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.6
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.45
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.97
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
3.73
Rat (Acute)
1.84
Rat (Chronic Oral)
3.02
Fathead Minnow
4.02
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
474.76
Hydration Free Energy
-13.12
Log(D) at pH=7.4
-1.4
Log(P)
-0.88
Log S
-1.56
Log(Vapor Pressure)
-12.33
Melting Point
175.79
pKa Acid
4.13
pKa Basic
6.21
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 0.9270
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9270
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9146
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9146
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9123
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9123
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8921
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8921
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8661
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8661
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8654
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8654
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8429
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8429
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8362
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8362
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8229
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8229
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8210
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8210
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8184
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8184
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8058
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8058
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8050
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8050
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7914
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7914
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7885
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7885
2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI Escherichia coli 3 0.7872
2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI Escherichia coli 3 0.7872
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7841
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7841
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7785
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.7785
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7776
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7776
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7773
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7773
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7723
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7723
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7662
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7662
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.7628
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.7628
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7624
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7624
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7606
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7606
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7560
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7560
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7556
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7556
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7489
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7489
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7471
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7471
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7449
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7449
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7434
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7434
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7391
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7391
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7373
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7373
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7365
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7365
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7312
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7312
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7297
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7297
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.7297
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 4 0.7297
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7295
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7295
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7252
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 4 0.7252
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7248
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7248
Poly(A) polymerase, putative Q381M1 Q381M1_TRYB2 Trypanosoma brucei brucei 4 0.7248
Poly(A) polymerase, putative Q381M1 Q381M1_TRYB2 Trypanosoma brucei brucei 4 0.7248
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7237
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7237
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7232
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7232
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7222
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7222
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7216
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7216
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7215
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7215
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7192
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7192
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7186
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7186
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7181
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7181
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7179
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7179
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7148
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7148
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7144
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7144
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7123
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7123
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7117
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7117
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7112
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7112
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7111
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7111
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7103
Avidin P02701 AVID_CHICK Gallus gallus 2 0.7103
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7087
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7087
Uncharacterized protein Q8DY32 Q8DY32_STRA5 Streptococcus agalactiae serotype V 4 0.7082
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7082
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7082
Uncharacterized protein Q8DY32 Q8DY32_STRA5 Streptococcus agalactiae serotype V 4 0.7082
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7037
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7037
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7032
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7032
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7017
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7017
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7008
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7008

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