(3R,4S,5S,6R)-2-(2-phenyl-4H-chromen-4-ylperoxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-3,4,5-triol - Compound Card

(3R,4S,5S,6R)-2-(2-phenyl-4H-chromen-4-ylperoxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-3,4,5-triol

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(3R,4S,5S,6R)-2-(2-phenyl-4H-chromen-4-ylperoxy)-tetrahydro-6-(hydroxymethyl)-2H-pyran-3,4,5-triol

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
Canonical Smiles OC[C@H]1OC(OOC2C=C(Oc3c2cccc3)c2ccccc2)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C21H22O8/c22-11-17-18(23)19(24)20(25)21(27-17)29-28-16-10-15(12-6-2-1-3-7-12)26-14-9-5-4-8-13(14)16/h1-10,16-25H,11H2/t16?,17-,18-,19+,20-,21?/m1/s1
InChIKey YDVUPJQQUBNDSO-OOFUGKDGSA-N
Formula C21H22O8
HBA 8
HBD 4
MW 402.4
Rotatable Bonds 5
TPSA 117.84
LogP 0.91
Number Rings 4
Number Aromatic Rings 2
Heavy Atom Count 29
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 402.13
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia helioscopia Euphorbiaceae Plantae 154990

Showing of synonyms

  • Mohamed AH, Hegazy MF, et al. (2012). Euphorbia helioscopia: Chemical constituents and biological activities. International Journal of Phytopharmacology,2012,3(1),78-90. [View]
Pubchem: 54503160

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(c3ccccc3)=CC2OOC4CCCCO4

Level: 2

Mol. Weight: 402.4 g/mol

Structure

SMILES: c1cccc(c12)OC=CC2OOC3CCCCO3

Level: 1

Mol. Weight: 402.4 g/mol

Structure

SMILES: c1ccccc1C(=CC2)Oc(c23)cccc3

Level: 1

Mol. Weight: 402.4 g/mol

Structure

SMILES: C1C=COc(c12)cccc2

Level: 0

Mol. Weight: 402.4 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 402.4 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 402.4 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.42
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.26
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.22

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.56
Plasma Protein Binding
72.16
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
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
6.94
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.17
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.95
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.88
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
-28.43
Rat (Acute)
2.44
Rat (Chronic Oral)
3.32
Fathead Minnow
4.17
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
443.97
Hydration Free Energy
-6.44
Log(D) at pH=7.4
1.93
Log(P)
1.07
Log S
-3.19
Log(Vapor Pressure)
-11.95
Melting Point
168.25
pKa Acid
7.46
pKa Basic
1.65
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9106
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9106
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8870
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8870
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8491
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8491
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8119
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8119
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8108
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8108
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8050
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8050
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8042
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.8042
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8031
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 3 0.8031
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7948
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7948
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7852
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 2 0.7852
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7831
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7831
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7768
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7768
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7738
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7738
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7713
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7713
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7698
Caspase-3 P42574 CASP3_HUMAN Homo sapiens 3 0.7698
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7632
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7632
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7608
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7606
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7606
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 2 0.7596
Kinesin-like protein KIF11 P52732 KIF11_HUMAN Homo sapiens 2 0.7596
Pyruvate kinase PKM P14618 KPYM_HUMAN Homo sapiens 3 0.7588
Pyruvate kinase PKM P14618 KPYM_HUMAN Homo sapiens 3 0.7588
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7565
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7565
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7557
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 3 0.7557
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7555
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7555
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7555
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 2 0.7555
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7542
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7542
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7523
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7523
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7518
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7518
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7511
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7511
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7510
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7510
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 2 0.7510
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7510
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7487
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7487
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7465
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 2 0.7465
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7427
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7427
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7404
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7404
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7397
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 2 0.7397
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7382
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7382
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7377
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7377
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7371
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7371
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7369
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7369
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7360
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7360
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7343
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 3 0.7343
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7329
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 2 0.7329
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7325
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.7325
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7288
Chymotrypsinogen A P00766 CTRA_BOVIN Bos taurus 3 0.7288
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 2 0.7272
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 2 0.7272
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7262
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7262
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7249
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7249
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7241
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7241
Neutrophil gelatinase-associated lipocalin P80188 NGAL_HUMAN Homo sapiens 2 0.7241
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7241
GTPase KRas P01116 RASK_HUMAN Homo sapiens 2 0.7233
GTPase KRas P01116 RASK_HUMAN Homo sapiens 2 0.7233
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7198
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7198
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7193
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7193
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7163
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7163
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7161
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7161
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7156
Carbonic anhydrase 4 Q64444 CAH4_MOUSE Mus musculus 2 0.7156
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7125
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7125
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7113
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7113
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 2 0.7094
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 2 0.7094
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7092
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7092
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7060
Cathepsin S P25774 CATS_HUMAN Homo sapiens 2 0.7060
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7055
Pantothenate kinase P9WPA7 COAA_MYCTU Mycobacterium tuberculosis 3 0.7055
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7039
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7039
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7034
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7034
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 2 0.7018
Proto-oncogene tyrosine-protein kinase Src P12931 SRC_HUMAN Homo sapiens 2 0.7018
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 2 0.7004
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 2 0.7004

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