5-O-feruloylquinic acid methyl ester - Compound Card

5-O-feruloylquinic acid methyl ester

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5-O-feruloylquinic acid methyl ester

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles COC(=O)[C@@]1(O)C[C@@H](OC(=O)/C=C/c2ccc(c(c2)OC)O)[C@@H]([C@@H](C1)O)O
InChI InChI=1S/C18H22O9/c1-25-13-7-10(3-5-11(13)19)4-6-15(21)27-14-9-18(24,17(23)26-2)8-12(20)16(14)22/h3-7,12,14,16,19-20,22,24H,8-9H2,1-2H3/b6-4+/t12-,14-,16-,18+/m1/s1
InChIKey CPYDMLXRLHYXSV-JVCGYDKASA-N
Formula C18H22O9
HBA 9
HBD 4
MW 382.37
Rotatable Bonds 5
TPSA 142.75
LogP -0.25
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.44
Exact Mass 382.13
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: 24813764
Nmrshiftdb2: 60021929

No compound-protein relationship available.

Structure

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 382.37 g/mol

Structure

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 382.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 382.37 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-5.5
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.850
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.54

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.540
Plasma Protein Binding
56.55
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
8.090
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-0.810
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
6.450
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-5.160
Rat (Acute)
2.000
Rat (Chronic Oral)
3.370
Fathead Minnow
4.090
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Toxic
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
423.530
Hydration Free Energy
-12.740
Log(D) at pH=7.4
0.960
Log(P)
0.45
Log S
-2.37
Log(Vapor Pressure)
-8.35
Melting Point
159.9
pKa Acid
6.31
pKa Basic
2.78
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 0.9519
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9467
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8986
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8950
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8940
Caffeic acid O-methyltransferase Q9ZTU2 Q9ZTU2_LOLPR Lolium perenne 4 0.8885
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8848
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8814
Thermolysin P00800 THER_BACTH Bacillus thermoproteolyticus 3 0.8730
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8690
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8644
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8517
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8338
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8309
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8266
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.8183
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.8177
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 2 0.8134
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.8130
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8128
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8102
Pantothenate synthetase P9WIL5 PANC_MYCTU Mycobacterium tuberculosis 3 0.7975
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7779
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7655
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7647
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7635
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7610
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7541
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7540
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7531
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7448
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7438
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 3 0.7435
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7418
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7400
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7389
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7362
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7342
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7328
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7327
Histone-lysine N-methyltransferase, H3 lysine-9 specific SUVH4 Q8GZB6 SUVH4_ARATH Arabidopsis thaliana 3 0.7291
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 4 0.7287
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 2 0.7263
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7257
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7255
Histone-lysine N-methyltransferase EHMT2 Q96KQ7 EHMT2_HUMAN Homo sapiens 3 0.7252
Dihydrofolate reductase P00378 DYR_CHICK Gallus gallus 3 0.7246
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7245
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 2 0.7241
Histone-lysine N-methyltransferase 2C Q8NEZ4 KMT2C_HUMAN Homo sapiens 3 0.7224
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 2 0.7206
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7186
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7153
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7151
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 4 0.7150
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7142
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7126
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 2 0.7126
Histone-lysine N-methyltransferase 2A Q03164 KMT2A_HUMAN Homo sapiens 3 0.7123
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7122
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7104
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7086
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 2 0.7082
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7081
Histone-lysine N-methyltransferase EHMT1 Q9H9B1 EHMT1_HUMAN Homo sapiens 3 0.7079
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7071
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7058
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7055
Myosin heavy chain, striated muscle P24733 MYS_ARGIR Argopecten irradians 3 0.7054
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 3 0.7045
DNA (cytosine-5)-methyltransferase 3A O88508 DNM3A_MOUSE Mus musculus 3 0.7045
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7044
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7037
Kynurenine--oxoglutarate transaminase 1 Q16773 KAT1_HUMAN Homo sapiens 2 0.7017
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 2 0.7014
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 3 0.7008
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial Q8N5Z0 AADAT_HUMAN Homo sapiens 2 0.7001
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 2 0.7000

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