(Z)-p-coumaroyl-1-O-beta-D-glucopyranoside - Compound Card

(Z)-p-coumaroyl-1-O-beta-D-glucopyranoside

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(Z)-p-coumaroyl-1-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Phenolic
    • Subclass: Phenolic Glycoside
Canonical Smiles OC[C@H]1O[C@@H](OC(=O)/C=C\c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C15H18O8/c16-7-10-12(19)13(20)14(21)15(22-10)23-11(18)6-3-8-1-4-9(17)5-2-8/h1-6,10,12-17,19-21H,7H2/b6-3-/t10-,12-,13+,14-,15+/m1/s1
InChIKey DSNCQKUYZOSARM-CIDNPRDCSA-N
Formula C15H18O8
HBA 8
HBD 5
MW 326.3
Rotatable Bonds 4
TPSA 136.68
LogP -1.25
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 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: 162954369
Nmrshiftdb2: 70003088

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C=Cc2ccccc2

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

Antioxidant

Absorption

Caco-2 (logPapp)
-5.41
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.54
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.87

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.75
Plasma Protein Binding
56.19
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
7.03
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.82
Biodegradation
Toxic
Carcinogenesis
Toxic
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.03
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.14
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
-2.88
Rat (Acute)
2.07
Rat (Chronic Oral)
3.26
Fathead Minnow
4.05
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
462.03
Hydration Free Energy
-19.47
Log(D) at pH=7.4
-0.12
Log(P)
-0.58
Log S
-1.51
Log(Vapor Pressure)
-11.95
Melting Point
155.64
pKa Acid
5.99
pKa Basic
5.33
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.9369
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9003
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.8828
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8697
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 4 0.8544
Trichothecene 15-O-acetyltransferase TRI3 Q9C1B7 TRI3_FUSSP Fusarium sporotrichioides 3 0.8513
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8490
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8452
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8425
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8258
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8043
Methionine aminopeptidase P0AE18 MAP1_ECOLI Escherichia coli 3 0.7951
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7821
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7805
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7693
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7605
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7582
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7545
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7539
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7536
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7522
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7513
Ribosome-inactivating protein alpha-trichosanthin P09989 RIPT_TRIKI Trichosanthes kirilowii 3 0.7485
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7441
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 3 0.7401
Probable nicotinate-nucleotide adenylyltransferase Q9HX21 NADD_PSEAE Pseudomonas aeruginosa 3 0.7367
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7351
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7348
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7334
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7324
Precorrin-3 methylase O68097 O68097_RHOCA Rhodobacter capsulatus 3 0.7268
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7251
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7245
NTPase P4 Q94M05 Q94M05_9VIRU Pseudomonas phage phi12 3 0.7233
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7211
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7210
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7205
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7186
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7177
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7174
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7154
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7107
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7105
Purine nucleoside phosphorylase DeoD-type B1JL34 DEOD_YERPY Yersinia pseudotuberculosis serotype O:3 2 0.7103
Holliday junction branch migration complex subunit RuvB Q9PMT7 RUVB_CAMJE Campylobacter jejuni subsp. jejuni serotype O:2 2 0.7092
Purine nucleoside phosphorylase DeoD-type O34925 DEOD_BACSU Bacillus subtilis 3 0.7089
Protocatechuate 3,4-dioxygenase beta chain P00437 PCXB_PSEPU Pseudomonas putida 2 0.7039
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7038
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 3 0.7031
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7029
UTP-monosaccharide-1-phosphate uridylyltransferase D3G6S4 D3G6S4_LEIMA Leishmania major 3 0.7009

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