2-hydroxy-5-(2-hydroxyphenoxy) phenoxy-beta-glucopyranoside - Compound Card

2-hydroxy-5-(2-hydroxyphenoxy) phenoxy-beta-glucopyranoside

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2-hydroxy-5-(2-hydroxyphenoxy) phenoxy-beta-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Salicaceae
  • Kingdom: Plantae
  • Class: Phenolic
Canonical Smiles OC[C@@H]1O[C@H](Oc2cc(ccc2O)Oc2ccccc2O)[C@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C18H20O9/c19-8-14-15(22)16(23)17(24)18(27-14)26-13-7-9(5-6-11(13)21)25-12-4-2-1-3-10(12)20/h1-7,14-24H,8H2/t14-,15-,16+,17-,18-/m0/s1
InChIKey NRKVEGHHZIQBBL-JCECYMMASA-N
Formula C18H20O9
HBA 9
HBD 6
MW 380.35
Rotatable Bonds 5
TPSA 149.07
LogP 0.07
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 380.11
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Flacourtia rukam Salicaceae Plantae 1085434

Showing of synonyms

  • Afifi N.I, Moawad A.S, et al. (2022). Four new phenolics and antiparasitic secondary metabolites from Flacourtia rukam Zoll. & Mortizi. Natural product research, 2022, 36(14), 3626-3637. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1Oc2cc(ccc2)OC3CCCCO3

Level: 2

Mol. Weight: 380.35 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 380.35 g/mol

Structure

SMILES: c1ccccc1Oc2ccccc2

Level: 1

Mol. Weight: 380.35 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 380.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 380.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.43
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
-1.29

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.090
Plasma Protein Binding
82.69
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
13.040
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.890
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.360
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.370
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
-5.510
Rat (Acute)
2.120
Rat (Chronic Oral)
3.720
Fathead Minnow
3.990
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
488.190
Hydration Free Energy
-12.580
Log(D) at pH=7.4
0.730
Log(P)
-
Log S
-4.09
Log(Vapor Pressure)
-10.75
Melting Point
200.49
pKa Acid
5.61
pKa Basic
4.18
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 0.9680
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.9427
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.9417
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.9408
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.9283
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9251
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9239
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.9167
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.9111
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8996
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.8909
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8901
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8757
Inorganic pyrophosphatase Q3JUV5 Q3JUV5_BURP1 Burkholderia pseudomallei 3 0.8659
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 3 0.8616
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.8611
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8609
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8582
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8517
Beta-lactoglobulin P02754 LACB_BOVIN Bos taurus 3 0.8489
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8488
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8444
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.8430
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8383
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8378
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8350
Putative HMP/thiamine-binding protein YkoF O34911 YKOF_BACSU Bacillus subtilis 3 0.8299
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.8247
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.8241
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8213
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8188
Cholinesterase P06276 CHLE_HUMAN Homo sapiens 3 0.8139
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.8109
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.8104
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8092
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8061
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8060
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8055
Aurora kinase A O14965 AURKA_HUMAN Homo sapiens 3 0.8012
Matrix metalloproteinase-9 P14780 MMP9_HUMAN Homo sapiens 3 0.8010
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7991
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7972
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7929
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7883
Steroid C26-monooxygenase P9WPP1 CP125_MYCTU Mycobacterium tuberculosis 3 0.7866
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7860
TetR family transcriptional regulator Q58L87 Q58L87_MYCSM Mycolicibacterium smegmatis 3 0.7809
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7803
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7795
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7771
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7769
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7761
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7760
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7749
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7748
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7741
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7739
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7708
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7696
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.7692
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7690
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7677
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7664
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7637
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7628
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7606
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7606
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7596
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7595
Thymidylate synthase P45352 TYSY_RAT Rattus norvegicus 2 0.7581
Hematopoietic prostaglandin D synthase O60760 HPGDS_HUMAN Homo sapiens 3 0.7574
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7572
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.7571
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7557
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7538
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7537
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7534
Uncharacterized protein YML079W Q03629 YMH9_YEAST Saccharomyces cerevisiae 3 0.7518
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7516
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7514
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7512
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7511
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7507
Tubulin alpha chain D0VWZ0 D0VWZ0_SHEEP Ovis aries 3 0.7506
Oxygen-insensitive NADPH nitroreductase O25608 RDXA_HELPY Helicobacter pylori 5 0.7496
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase Q3JRA0 ISPF_BURP1 Burkholderia pseudomallei 3 0.7493
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7492
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7490
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 4 0.7480
Pyruvate dehydrogenase [ubiquinone] P07003 POXB_ECOLI Escherichia coli 3 0.7452
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7439
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7435
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7434
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7432
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 3 0.7432
11-beta-hydroxysteroid dehydrogenase 1 P50172 DHI1_MOUSE Mus musculus 3 0.7419
Pyridoxal kinase P82197 PDXK_SHEEP Ovis aries 3 0.7418
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7408
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7403
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7396
NmrA-like family domain-containing protein 1 Q9HBL8 NMRL1_HUMAN Homo sapiens 2 0.7373
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7360
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7359
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7359
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7351
F420-dependent NADP reductase O29370 FNO_ARCFU Archaeoglobus fulgidus 4 0.7347
Caffeoyl-CoA O-methyltransferase Q40313 CAMT_MEDSA Medicago sativa 3 0.7335
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7323
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7321
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7315
Succinyl-CoA:acetate CoA-transferase B3EY95 SCACT_ACEAC Acetobacter aceti 3 0.7299
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 3 0.7264
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7251
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7247
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7233
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7232
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7227
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7227
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7223
Renin P00797 RENI_HUMAN Homo sapiens 3 0.7221
F420H(2)-dependent reductase Rv1155 O06553 F420R_MYCTU Mycobacterium tuberculosis 3 0.7212
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7204
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7195
Cyclic GMP-AMP phosphodiesterase SMPDL3A Q92484 ASM3A_HUMAN Homo sapiens 2 0.7190
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7173
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 2 0.7172
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7157
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7155
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7151
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7137
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7131
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7130
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 3 0.7121
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7110
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7099
Gentisate 1,2-dioxygenase Q67FT0 Q67FT0_PSESE Pseudaminobacter salicylatoxidans 2 0.7098
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7092
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7079
Eukaryotic translation initiation factor 4E type 3 Q9DBB5 IF4E3_MOUSE Mus musculus 3 0.7077
Elongation factor Tu 1 P0CE47 EFTU1_ECOLI Escherichia coli 3 0.7068
Diguanylate phosphodiesterase A6T8V8 A6T8V8_KLEP7 Klebsiella pneumoniae subsp. pneumoniae 4 0.7055
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 2 0.7054
Phenazine biosynthesis protein A/B Q396C9 Q396C9_BURL3 Burkholderia lata 3 0.7051
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7041
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7040
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7013
Streptavidin P22629 SAV_STRAV Streptomyces avidinii 3 0.7011
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7008

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