4-O-caffeoylquinic acid methyl ester - Compound Card

4-O-caffeoylquinic acid methyl ester

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4-O-caffeoylquinic acid methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles COC(=O)C1(O)C[C@@H](O)C([C@@H](C1)O)OC(=O)/C=C/c1ccc(c(c1)O)O
InChI InChI=1S/C17H20O9/c1-25-16(23)17(24)7-12(20)15(13(21)8-17)26-14(22)5-3-9-2-4-10(18)11(19)6-9/h2-6,12-13,15,18-21,24H,7-8H2,1H3/b5-3+/t12-,13-,15?,17?/m1/s1
InChIKey SMFKCIHIAHWGGL-JUEQGWKHSA-N
Formula C17H20O9
HBA 9
HBD 5
MW 368.34
Rotatable Bonds 4
TPSA 153.75
LogP -0.56
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 26
Formal Charge 0
Fraction CSP3 0.41
Exact Mass 368.11
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia gaditana Euphorbiaceae Plantae 3990

Showing of synonyms

  • Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]
Pubchem: 71720840
Nmrshiftdb2: 70128914

No compound-protein relationship available.

Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 368.34 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 368.34 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 368.34 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-5.85
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.920
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.38

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.560
Plasma Protein Binding
45.18
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
10.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.930
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.630
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.620
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
-2.620
Rat (Acute)
1.930
Rat (Chronic Oral)
3.360
Fathead Minnow
4.120
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
447.310
Hydration Free Energy
-14.330
Log(D) at pH=7.4
0.450
Log(P)
0.34
Log S
-2.45
Log(Vapor Pressure)
-8.44
Melting Point
173.55
pKa Acid
5.98
pKa Basic
4.25
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 0.9259
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.9216
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.9135
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9120
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9038
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8903
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8791
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8721
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.8568
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8424
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8361
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8256
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8229
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.8227
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8226
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8121
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7997
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 3 0.7970
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7957
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7927
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7903
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.7883
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7880
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7880
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7769
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7720
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7673
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7651
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7651
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7644
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7616
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7545
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7525
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.7510
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7495
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7466
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7448
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7436
Eukaryotic translation initiation factor 4E-1 P29557 IF4E1_WHEAT Triticum aestivum 4 0.7431
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7396
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7380
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7364
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7356
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7316
Phosphatidylinositol 5-phosphate 4-kinase type-2 beta P78356 PI42B_HUMAN Homo sapiens 3 0.7309
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7308
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7307
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7296
Serine/threonine-protein kinase RAD53 P22216 RAD53_YEAST Saccharomyces cerevisiae 4 0.7293
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7240
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7231
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7231
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7221
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7205
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7198
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7191
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7162
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7151
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7148
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7143
Ribosomal RNA small subunit methyltransferase NEP1 Q06287 NEP1_YEAST Saccharomyces cerevisiae 4 0.7122
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7120
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7117
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7105
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7100
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7090
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7088
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7074
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7073
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.7062
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7042
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7003
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7002

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