5-O-caffeoyl quinic acid - Compound Card

5-O-caffeoyl quinic acid

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5-O-caffeoyl quinic acid

Structure
Zoomed Structure
  • Family: Plantae - Apiaceae
  • Kingdom: Plantae
  • Class: Cinnamic Acid Derivative
Canonical Smiles O=C(O[C@@H]1CC(O)(C[C@H](C1O)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(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14?,16?/m1/s1
InChIKey CWVRJTMFETXNAD-AVXJPILUSA-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 Pituranthos scoparius Apiaceae Plantae 489362

Showing of synonyms

  • Dahia M, Siracusa L, et al. (2009). Constituents of the polar extracts from Algerian Pituranthos scoparius. Natural Product Communications,2009,4(12),1691-1692. [View] [PubMed]
Pubchem: 147305083

No compound-protein relationship available.

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)
-6.45
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.13
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.62

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.64
Plasma Protein Binding
46.13
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
6.37
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-2.2
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.63
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.16
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
0.07
Rat (Acute)
1.87
Rat (Chronic Oral)
3.29
Fathead Minnow
3.89
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
453.94
Hydration Free Energy
-9.38
Log(D) at pH=7.4
-0.99
Log(P)
-0.66
Log S
-1.32
Log(Vapor Pressure)
-13.41
Melting Point
202.11
pKa Acid
3.24
pKa Basic
7.02
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 0.9274
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9274
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9176
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9176
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9149
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9149
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9117
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8813
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8813
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8647
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8647
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8638
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8638
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8635
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8635
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.8607
Shikimate dehydrogenase (NADP(+)) P56119 AROE_HELPY Helicobacter pylori 3 0.8607
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8567
Albumin P02768 ALBU_HUMAN Homo sapiens 3 0.8567
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8400
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8400
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8377
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8377
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8363
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8363
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8278
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8278
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8209
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8209
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8184
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8184
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8178
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8178
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8090
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.8090
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8074
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8027
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8027
2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI Escherichia coli 3 0.7916
2-dehydro-3-deoxyphosphooctonate aldolase P0A715 KDSA_ECOLI Escherichia coli 3 0.7916
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7899
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7899
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7894
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7894
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7890
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7890
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7882
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7882
Ectonucleoside triphosphate diphosphohydrolase I Q5ZUA2 Q5ZUA2_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7876
Ectonucleoside triphosphate diphosphohydrolase I Q5ZUA2 Q5ZUA2_LEGPH Legionella pneumophila subsp. pneumophila 3 0.7876
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7866
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7866
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7832
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7832
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7779
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7779
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7734
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7734
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7725
Aspartate carbamoyltransferase catalytic subunit P0A786 PYRB_ECOLI Escherichia coli 3 0.7725
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.7695
Carboxyethyl-arginine beta-lactam-synthase P0DJQ7 BLS_STRCL Streptomyces clavuligerus 3 0.7695
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.7679
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase B1MKD5 B1MKD5_MYCA9 Mycobacteroides abscessus 3 0.7679
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7675
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7675
3-dehydroquinate dehydratase P9WPX7 AROQ_MYCTU Mycobacterium tuberculosis 3 0.7629
3-dehydroquinate dehydratase P9WPX7 AROQ_MYCTU Mycobacterium tuberculosis 3 0.7629
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7619
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7619
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7521
5-formaminoimidazole-4-carboxamide-1-(beta)-D-ribofuranosyl 5'-monophosphate synthetase Q8U0R7 PURP_PYRFU Pyrococcus furiosus 3 0.7521
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7463
Hydroxymethylglutaryl-CoA synthase Q9FD71 HMGCS_ENTFL Enterococcus faecalis 2 0.7463
Mevalonate kinase Q4Q6K7 Q4Q6K7_LEIMA Leishmania major 3 0.7419
Mevalonate kinase Q4Q6K7 Q4Q6K7_LEIMA Leishmania major 3 0.7419
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7415
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7415
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7406
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7406
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7400
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7400
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7390
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7390
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7356
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7356
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7352
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.7352
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7317
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7317
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7276
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7276
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7274
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7274
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7228
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7228
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.7213
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 3 0.7213
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7210
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7210
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7205
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7205
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7190
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7190
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
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7178
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7178
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7145
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7145
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7138
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7138
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7129
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7129
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7127
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7127
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
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7111
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7111
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7090
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7090
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7059
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7059
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7059
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7059
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7040
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7038
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7038
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7033
Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 Q9Y3Z3 SAMH1_HUMAN Homo sapiens 3 0.7033
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7024
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7024
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7020
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7020
tRNA (guanine-N(1)-)-methyltransferase Q2GIL5 TRMD_ANAPZ Anaplasma phagocytophilum 3 0.7003
tRNA (guanine-N(1)-)-methyltransferase Q2GIL5 TRMD_ANAPZ Anaplasma phagocytophilum 3 0.7003

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