3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2-methoxyphenoxy]-propyl-beta-D-glucopyranoside - Compound Card

3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2-methoxyphenoxy]-propyl-beta-D-glucopyranoside

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3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2-methoxyphenoxy]-propyl-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Solanaceae
  • Kingdom: Plantae
  • Class: Lignan
Canonical Smiles OC/C=C/c1ccc(c(c1)OC)O[C@H]([C@@H](c1ccc(c(c1)OC)O)O[C@H]1O[C@@H](CO)[C@@H]([C@H]([C@@H]1O)O)O)CO
InChI InChI=1S/C26H34O12/c1-34-18-11-15(6-7-16(18)30)25(38-26-24(33)23(32)22(31)20(12-28)37-26)21(13-29)36-17-8-5-14(4-3-9-27)10-19(17)35-2/h3-8,10-11,20-33H,9,12-13H2,1-2H3/b4-3+/t20-,21-,22-,23+,24-,25+,26+/m0/s1
InChIKey MNLWSKFTELUKMW-JTOXUZPZSA-N
Formula C26H34O12
HBA 12
HBD 7
MW 538.55
Rotatable Bonds 12
TPSA 187.76
LogP -0.29
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 38
Formal Charge 0
Fraction CSP3 0.46
Exact Mass 538.21
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Lycium schweinfurthii Solanaceae Plantae 416539
2 Lycium schweinfurthii Solanaceae Plantae 416539

Showing of synonyms

  • Elbermawi A, Halim A.F, et al. (2021). A new glucoside with a potent α-glucosidase inhibitory activity from Lycium schweinfurthii. Natural product research,2021, 35(6), 976-983. [View] [PubMed]
  • Elbermawi A, Halim A.F, et al. (2022). Lycium schweinfurthii: new secondary metabolites and their cytotoxic activities. Natural product research,2022, 36(20), 5134-5141. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(c2ccccc2)COc3ccccc3

Level: 2

Mol. Weight: 538.55 g/mol

Structure

SMILES: c1ccccc1OCCOC2CCCCO2

Level: 1

Mol. Weight: 538.55 g/mol

Structure

SMILES: c1ccccc1CCOc2ccccc2

Level: 1

Mol. Weight: 538.55 g/mol

Structure

SMILES: c1ccccc1COC2CCCCO2

Level: 1

Mol. Weight: 538.55 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 538.55 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 538.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.2
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.07
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.37

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.87
Plasma Protein Binding
71.52
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
9.66
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.27
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.75
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.94
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
-1228.0
Rat (Acute)
2.4
Rat (Chronic Oral)
4.1
Fathead Minnow
4.86
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
527.79
Hydration Free Energy
-2.93
Log(D) at pH=7.4
0.71
Log(P)
-0.91
Log S
-3.68
Log(Vapor Pressure)
-10.88
Melting Point
159.72
pKa Acid
5.32
pKa Basic
3.12
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 0.9357
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8784
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8517
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.8443
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8381
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.8363
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8201
N-alpha-acetyltransferase 50 Q9GZZ1 NAA50_HUMAN Homo sapiens 3 0.7837
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7820
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7775
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7727
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.7574
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7560
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7534
Oxygenase Q194P4 Q194P4_STRAA Streptomyces argillaceus 4 0.7521
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7473
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7451
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7449
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7418
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7418
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7412
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 3 0.7303
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7299
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7272
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7270
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7241
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7204
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.7156
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7152
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7139
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7105
Acyl-homoserine-lactone synthase Q4VSJ8 Q4VSJ8_BURGL Burkholderia glumae 4 0.7099
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7036
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7022
14-3-3 protein gamma P61981 1433G_HUMAN Homo sapiens 3 0.7020
Seminal ribonuclease P00669 RNS_BOVIN Bos taurus 3 0.7000

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