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1-(alpha-L-rhamnosyl-(1→6)-O-beta-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene
- Family: Plantae - Bignoniaceae
- Kingdom: Plantae
- Class: Phenolic
| Canonical Smiles | COc1cc(OC2OC(COC3OC(C)C(C(C3O)O)O)C(C(C2O)O)O)cc(c1OC)OC |
|---|---|
| InChI | InChI=1S/C21H32O13/c1-8-13(22)15(24)17(26)20(32-8)31-7-12-14(23)16(25)18(27)21(34-12)33-9-5-10(28-2)19(30-4)11(6-9)29-3/h5-6,8,12-18,20-27H,7H2,1-4H3 |
| InChIKey | FNPXSSIBZAQOBP-UHFFFAOYSA-N |
| Formula | C21H32O13 |
| HBA | 13 |
| HBD | 6 |
| MW | 492.47 |
| Rotatable Bonds | 8 |
| TPSA | 185.99 |
| LogP | -2.26 |
| Number Rings | 3 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 34 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.71 |
| Exact Mass | 492.18 |
| Number of Lipinski Rule Violations | 2 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Tecoma mollis | Bignoniaceae | Plantae | 2822953 |
Showing of synonyms
1-(alpha-L-rhamnosyl-(1→6)-O-beta-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene
Antiarol rutinoside
261351-23-9
Antiarol rutiside
2-methyl-6-[[3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy]oxane-3,4,5-triol
1-(alpha-L-Rhamnosyl-(1-->6)-O-beta-D-glucopyranosyloxy)-3,4,5-trimethoxybenzene
3,4,5-Trimethoxyphenyl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
2-methyl-6-{[3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxane-3,4,5-triol
SCHEMBL14365675
- Abdel-Mageed W, Al-Wahaibi L, et al. (2017). New phenolic glycosides with cyclooxygenase inhibition from the roots of Tecoma mollis. Phytochemistry Letters, 2017, 21, 98-103. [View]
No compound-protein relationship available.
SMILES: O1CCCCC1OCC2CCCC(O2)Oc3ccccc3
Level: 2
Mol. Weight: 492.47 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 492.47 g/mol
SMILES: c1ccccc1OC2CCCCO2
Level: 1
Mol. Weight: 492.47 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 492.47 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 492.47 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.12
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.150
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.45
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.790
- Plasma Protein Binding
- -5.12
- 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
- 6.250
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.880
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.090
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.650
- 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
- -142.560
- Rat (Acute)
- 2.200
- Rat (Chronic Oral)
- 4.010
- Fathead Minnow
- 3.700
- 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
- 497.070
- Hydration Free Energy
- -3.410
- Log(D) at pH=7.4
- -0.570
- Log(P)
- -1.4
- Log S
- -2.29
- Log(Vapor Pressure)
- -12.56
- Melting Point
- 154.69
- pKa Acid
- 6.29
- pKa Basic
- 1.34
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.9223 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8672 |
| Mitogen-activated protein kinase 1 | P28482 | MK01_HUMAN | Homo sapiens | 3 | 0.8362 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.8344 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.8256 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8202 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | P48736 | PK3CG_HUMAN | Homo sapiens | 3 | 0.8187 |
| RNA-dependent RNA polymerase | Q6A562 | Q6A562_9VIRU | Thosea asigna virus | 3 | 0.8177 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8170 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7968 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7858 |
| Proton-gated ion channel | Q7NDN8 | GLIC_GLOVI | Gloeobacter violaceus | 3 | 0.7672 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7580 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7543 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 3 | 0.7543 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7417 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 2 | 0.7381 |
| HTH-type transcriptional repressor PurR | P0ACP7 | PURR_ECOLI | Escherichia coli | 2 | 0.7380 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7329 |
| Cyclin-dependent kinase 9 | P50750 | CDK9_HUMAN | Homo sapiens | 3 | 0.7282 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7271 |
| Adenylate cyclase type 5 | P30803 | ADCY5_CANLF | Canis lupus familiaris | 4 | 0.7223 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7177 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7095 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7090 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7085 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7083 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7055 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7055 |
| LIM domain kinase 1 | P53667 | LIMK1_HUMAN | Homo sapiens | 2 | 0.7053 |
| Mitogen-activated protein kinase 14 | Q16539 | MK14_HUMAN | Homo sapiens | 3 | 0.7052 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7031 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7010 |
| Purine nucleoside phosphorylase DeoD-type | P0ABP9 | DEOD_ECO57 | Escherichia coli O157:H7 | 3 | 0.7000 |