3-(O-beta-D-glucopyranosyl)-alpha-(O-beta-D-glucopyranosyl)-4-hydroxyphenylethanol - Compound Card

3-(O-beta-D-glucopyranosyl)-alpha-(O-beta-D-glucopyranosyl)-4-hydroxyphenylethanol

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3-(O-beta-D-glucopyranosyl)-alpha-(O-beta-D-glucopyranosyl)-4-hydroxyphenylethanol

Structure
Zoomed Structure
  • Family: Plantae - Lamiaceae
  • Kingdom: Plantae
  • Class: Terpenoid
    • Subclass: Iridoid Glycoside
Canonical Smiles OC[C@H]1O[C@@H](OCCc2ccc(c(c2)O[C@@H]2O[C@H](CO)[C@H]([C@@H]([C@H]2O)O)O)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C20H30O13/c21-6-11-13(24)15(26)17(28)19(32-11)30-4-3-8-1-2-9(23)10(5-8)31-20-18(29)16(27)14(25)12(7-22)33-20/h1-2,5,11-29H,3-4,6-7H2/t11-,12-,13-,14-,15+,16+,17-,18-,19-,20-/m1/s1
InChIKey SGXQDOGGNJBNCM-XSVWGIRKSA-N
Formula C20H30O13
HBA 13
HBD 9
MW 478.45
Rotatable Bonds 8
TPSA 218.99
LogP -4.07
Number Rings 3
Number Aromatic Rings 1
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.7
Exact Mass 478.17
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Teucrium polium Lamiaceae Plantae 1117157

Showing of synonyms

  • Elmasri W.A, Yang T, et al. (2015). Teucrium polium phenylethanol and iridoid glycoside characterization and flavonoid inhibition of biofilm-forming Staphylococcus aureus. Journal of natural products, 2015, 78(1), 2-9. [View] [PubMed]
Pubchem: 101910084

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OCCc2cc(ccc2)OC3CCCCO3

Level: 2

Mol. Weight: 478.45 g/mol

Structure

SMILES: c1ccccc1CCOC2CCCCO2

Level: 1

Mol. Weight: 478.45 g/mol

Structure

SMILES: c1ccccc1OC2CCCCO2

Level: 1

Mol. Weight: 478.45 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 478.45 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 478.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.4
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.480
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.93

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.690
Plasma Protein Binding
68.76
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
7.180
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.290
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.910
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
4.890
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
-100.090
Rat (Acute)
1.980
Rat (Chronic Oral)
4.410
Fathead Minnow
3.150
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
577.410
Hydration Free Energy
-3.950
Log(D) at pH=7.4
-1.690
Log(P)
-3.55
Log S
-1.48
Log(Vapor Pressure)
-18.59
Melting Point
205.1
pKa Acid
4.81
pKa Basic
5.76
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.8935
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.8666
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.8636
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8601
L-lactate dehydrogenase A chain P04642 LDHA_RAT Rattus norvegicus 3 0.8557
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8491
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8369
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8187
Lactoperoxidase P80025 PERL_BOVIN Bos taurus 3 0.8072
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8046
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8016
beta-glucosidase Q92AS9 Q92AS9_LISIN Listeria innocua serovar 6a 3 0.7726
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7550
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7526
Benzoylformate decarboxylase P20906 MDLC_PSEPU Pseudomonas putida 3 0.7317
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7288
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7158
Beta-galactosidase P00722 BGAL_ECOLI Escherichia coli 3 0.7123
Macrophage metalloelastase P39900 MMP12_HUMAN Homo sapiens 3 0.7048
Beta-glucosidase 1A Q25BW5 BGL1A_PHACH Phanerodontia chrysosporium 3 0.7014
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7000

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