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3,4-dihydroxy-beta-phenylethoxy-O-alpha-L-lyxopyranosyl-(1→2)-alpha-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-beta-D-glucopyranoside
- Family: Plantae - Labiateae
- Kingdom: Plantae
-
Class: Phenylpropanoid
- Subclass: Phenylpropanoid Glycoside
| Canonical Smiles | OCC1OC(OCCc2ccc(c(c2)O)O)C(C(C1OC(=O)/C=C/c1ccc(c(c1)O)O)OC1OC(C)C(C(C1OC1OCC(C(C1O)O)O)O)O)O |
|---|---|
| InChI | InChI=1S/C34H44O19/c1-14-24(42)26(44)31(53-32-27(45)25(43)21(40)13-48-32)34(49-14)52-30-28(46)33(47-9-8-16-3-6-18(37)20(39)11-16)50-22(12-35)29(30)51-23(41)7-4-15-2-5-17(36)19(38)10-15/h2-7,10-11,14,21-22,24-40,42-46H,8-9,12-13H2,1H3/b7-4+ |
| InChIKey | UDHCHDJLZGYDDM-QPJJXVBHSA-N |
| Formula | C34H44O19 |
| HBA | 19 |
| HBD | 11 |
| MW | 756.71 |
| Rotatable Bonds | 12 |
| TPSA | 304.21 |
| LogP | -2.55 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 53 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.56 |
| Exact Mass | 756.25 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Teucrium chamaedrys | Labiateae | Plantae | 53176 |
Showing of synonyms
3,4-dihydroxy-beta-phenylethoxy-O-alpha-L-lyxopyranosyl-(1→2)-alpha-L-rhamnopyranosyl-(1→3)-4-O-caffeoyl-beta-D-glucopyranoside
Compound NP-000173
MEGxp0_000054
MEGxp0_000787
ACon1_000604
ACon1_001732
AKOS040740182
NCGC00168920-01
NCGC00168920-02
NS00097498
BRD-A01993200-001-01-8
[4-[4,5-dihydroxy-6-methyl-3-(3,4,5-trihydroxyoxan-2-yl)oxyoxan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)oxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate
- Gross G, Lahloub M, et al. (1988). Teucrioside, A Phenylpropanoid Glycoside from Teucrium Chamaedrys. Phytochemistry, 1988, 27(5), 1459-1463. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1OC2C(OCCC2)OC3C(OC(=O)C=Cc4ccccc4)COC(C3)OCCc5ccccc5
Level: 4
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC(C2OC3CCCCO3)COC(C2)OCCc4ccccc4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC(COCC2)C2OC(OCCC3)C3OC4CCCCO4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC(OCC2)CC2OC(OCCC3)C3OC4CCCCO4
Level: 3
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC2CCC(OC2)OCCc3ccccc3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1C=CC(=O)OC(COCC2)C2OC3CCCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC(OCC2)CC2OC3CCCCO3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: O1CCCCC1OC2C(OCCC2)OC3CCOCC3
Level: 2
Mol. Weight: 756.71 g/mol
SMILES: C1OCCCC1OC(=O)C=Cc2ccccc2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1CCOC2CCCCO2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: C1COCCC1OC2CCCCO2
Level: 1
Mol. Weight: 756.71 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 756.71 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 756.71 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.67
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- 0.7
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 878.38
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.68
- Plasma Protein Binding
- -18.01
- 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
- 9.82
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -19.71
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.51
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.89
- 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
- -1594015.12
- Rat (Acute)
- 2.25
- Rat (Chronic Oral)
- 4.81
- Fathead Minnow
- 2021.04
- 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
- 173222.94
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -0.6
- Log(P)
- -0.94
- Log S
- -3.96
- Log(Vapor Pressure)
- -5692.16
- Melting Point
- 191.08
- pKa Acid
- -10.48
- pKa Basic
- 3.91
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9354 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.9279 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.8849 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.8733 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8460 |
| MAP kinase-activated protein kinase 2 | P49137 | MAPK2_HUMAN | Homo sapiens | 3 | 0.8440 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8362 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8304 |
| 2-aminohexano-6-lactam racemase | Q7M181 | ACLR_ACHOB | Achromobacter obae | 3 | 0.8229 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8090 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7979 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7973 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.7943 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7905 |
| Tubulin--tyrosine ligase | F6Z895 | A9ULH4_XENTR | Xenopus tropicalis | 4 | 0.7736 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7646 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7625 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7608 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.7602 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 3 | 0.7474 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7415 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7377 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7291 |
| Serine/threonine-protein kinase SKY1 | Q03656 | SKY1_YEAST | Saccharomyces cerevisiae | 2 | 0.7264 |
| Fibroblast growth factor receptor 2 | P21802 | FGFR2_HUMAN | Homo sapiens | 3 | 0.7245 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7235 |
| Dual specificity mitogen-activated protein kinase kinase 1 | Q02750 | MP2K1_HUMAN | Homo sapiens | 3 | 0.7227 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7213 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7209 |
| 3-hydroxyanthranilate 3,4-dioxygenase | Q1LCS4 | 3HAO_CUPMC | Cupriavidus metallidurans | 2 | 0.7201 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7190 |
| Ephrin type-B receptor 2 | P54763 | EPHB2_MOUSE | Mus musculus | 2 | 0.7173 |
| Purine nucleoside phosphorylase 2 | P45563 | XAPA_ECOLI | Escherichia coli | 3 | 0.7142 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7121 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 2 | 0.7097 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 3 | 0.7093 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7062 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7057 |
| Purine nucleoside phosphorylase | P55859 | PNPH_BOVIN | Bos taurus | 3 | 0.7051 |
| Dihydropteroate synthase | Q81VW8 | Q81VW8_BACAN | Bacillus anthracis | 3 | 0.7045 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.7045 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7045 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7039 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7003 |
| Histone-lysine N-methyltransferase EHMT1 | Q9H9B1 | EHMT1_HUMAN | Homo sapiens | 3 | 0.7001 |