Coumaric acid-O-hexoside - Compound Card

Coumaric acid-O-hexoside

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Coumaric acid-O-hexoside

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OCC1OC(Oc2ccc(cc2)/C=C/C(=O)O)C(C(C1O)O)O
InChI InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(23-10)22-9-4-1-8(2-5-9)3-6-11(17)18/h1-6,10,12-16,19-21H,7H2,(H,17,18)/b6-3+
InChIKey LJFYQZQUAULRDF-ZZXKWVIFSA-N
Formula C15H18O8
HBA 7
HBD 5
MW 326.3
Rotatable Bonds 5
TPSA 136.68
LogP -1.04
Number Rings 2
Number Aromatic Rings 1
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.4
Exact Mass 326.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Rosmarinuseriocalyx Lamiaceae Plantae —

Showing of synonyms

  • Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
Pubchem: 13783633
Nmrshiftdb2: 80001309

No compound-protein relationship available.

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 326.3 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 326.3 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 326.3 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.64
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-4.83
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.95

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.65
Plasma Protein Binding
3.05
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
4.05
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.04
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.91
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
3.84
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
0.87
Rat (Acute)
1.65
Rat (Chronic Oral)
3.48
Fathead Minnow
4.11
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
441.78
Hydration Free Energy
-15.17
Log(D) at pH=7.4
-2.43
Log(P)
-0.33
Log S
-1.64
Log(Vapor Pressure)
-10.34
Melting Point
171.81
pKa Acid
3.72
pKa Basic
4.11
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.9199
Peptide deformylase 1B, chloroplastic/mitochondrial Q9FUZ2 DEF1B_ARATH Arabidopsis thaliana 3 0.8788
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.8626
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8605
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.8598
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8534
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8331
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8014
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7838
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7811
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7801
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7758
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 3 0.7727
Beta-glucosidase 12 B8AVF0 BGL12_ORYSI Oryza sativa subsp. indica 3 0.7716
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7701
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 2 0.7626
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7607
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7549
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7532
Strictosidine-O-beta-D-glucosidase Q8GU20 SG1_RAUSE Rauvolfia serpentina 5 0.7457
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7427
Purine nucleoside phosphorylase DeoD-type P0ABP9 DEOD_ECO57 Escherichia coli O157:H7 3 0.7421
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7401
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7383
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7297
Putative b-glycan phosphorylase Q21MB1 Q21MB1_SACD2 Saccharophagus degradans 4 0.7269
Nucleoside diphosphate kinase Q5UQL3 NDK_MIMIV Acanthamoeba polyphaga mimivirus 2 0.7264
5-formyltetrahydrofolate cyclo-ligase P75430 MTHFS_MYCPN Mycoplasma pneumoniae 2 0.7263
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7246
Alpha-aminoadipic semialdehyde dehydrogenase P49419 AL7A1_HUMAN Homo sapiens 3 0.7234
N-terminal acetyltransferase A complex subunit NAT1 P12945 NAT1_YEAST Saccharomyces cerevisiae 2 0.7219
Aminopeptidase N P15145 AMPN_PIG Sus scrofa 2 0.7212
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7206
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7202
Galactoside O-acetyltransferase P07464 THGA_ECOLI Escherichia coli 4 0.7178
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7172
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.7166
cGMP-dependent protein kinase 2 Q13237 KGP2_HUMAN Homo sapiens 3 0.7148
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7126
Adenosine 5'-monophosphoramidase HINT1 P80912 HINT1_RABIT Oryctolagus cuniculus 3 0.7120
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7117
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 2 0.7108
ATP-dependent helicase/nuclease subunit A P23478 ADDA_BACSU Bacillus subtilis 2 0.7098
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7096
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7086
Retinal dehydrogenase 2 O94788 AL1A2_HUMAN Homo sapiens 3 0.7007

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