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9-O-beta-xylopyranosyl-(1→6)-O-beta-glucopyranosyl-(1→6)-O-beta-glucopyranosyl trans-cinnamyl alcohol
- Family: Plantae - Acanthaceae
- Kingdom: Plantae
-
Class: Glycoside
- Subclass: Cinnamyl Alcohol Glycoside
| Canonical Smiles | O[C@@H]1C(CO[C@H]2OC(CO[C@@]3(O)OC[C@H](C([C@@H]3O)O)O)[C@H](C([C@@H]2O)O)O)O[C@@H]([C@H](C1O)O)OC/C=C/c1ccccc1 |
|---|---|
| InChI | InChI=1S/C26H38O16/c27-13-9-39-26(36,23(35)16(13)28)40-11-15-18(30)20(32)22(34)25(42-15)38-10-14-17(29)19(31)21(33)24(41-14)37-8-4-7-12-5-2-1-3-6-12/h1-7,13-25,27-36H,8-11H2/b7-4+/t13-,14?,15?,16?,17-,18-,19?,20?,21+,22+,23+,24+,25+,26+/m1/s1 |
| InChIKey | MQZYEDFNJPUADD-QAHOPEEMSA-N |
| Formula | C26H38O16 |
| HBA | 16 |
| HBD | 10 |
| MW | 606.57 |
| Rotatable Bonds | 10 |
| TPSA | 257.68 |
| LogP | -4.88 |
| Number Rings | 4 |
| Number Aromatic Rings | 1 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.69 |
| Exact Mass | 606.22 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Sanchezia nobilis | Acanthaceae | Plantae | 71612 |
Showing of synonyms
9-O-beta-xylopyranosyl-(1→6)-O-beta-glucopyranosyl-(1→6)-O-beta-glucopyranosyl trans-cinnamyl alcohol
- Abd Ellah AE, Mohamed KM, et al. (2014). Cinnamyl alcohol, benzyl alcohol, and flavonoid glycosides from Sanchezia nobilis. Chemistry of Natural Compounds,2014,50(5),823-826. [View]
No compound-protein relationship available.
SMILES: c1ccccc1C=CCOC(O2)CCCC2COC(O3)CCCC3COC4CCCCO4
Level: 3
Mol. Weight: 606.57 g/mol
SMILES: c1ccccc1C=CCOC(O2)CCCC2COC3CCCCO3
Level: 2
Mol. Weight: 606.57 g/mol
SMILES: O1CCCCC1OCC2CCCC(O2)OCC3CCCCO3
Level: 2
Mol. Weight: 606.57 g/mol
SMILES: c1ccccc1C=CCOC2CCCCO2
Level: 1
Mol. Weight: 606.57 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 606.57 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 606.57 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 606.57 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.43
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.16
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 4.43
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.89
- Plasma Protein Binding
- 43.7
- 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
- 3.99
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -4.36
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.13
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 5.76
- Micronucleos
- Safe
- 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
- -8234.44
- Rat (Acute)
- 2.42
- Rat (Chronic Oral)
- 4.32
- Fathead Minnow
- 16.17
- 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
- 409.79
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -0.99
- Log(P)
- -3.25
- Log S
- -1.31
- Log(Vapor Pressure)
- -12.92
- Melting Point
- 168.78
- pKa Acid
- 1.65
- pKa Basic
- 4.22
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8681 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8681 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8642 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8642 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8321 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.8321 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8223 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8223 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7998 |
| 2',3'-cyclic-nucleotide 3'-phosphodiesterase | P16330 | CN37_MOUSE | Mus musculus | 3 | 0.7998 |
| Disintegrin and metalloproteinase domain-containing protein 17 | P78536 | ADA17_HUMAN | Homo sapiens | 3 | 0.7850 |
| Disintegrin and metalloproteinase domain-containing protein 17 | P78536 | ADA17_HUMAN | Homo sapiens | 3 | 0.7850 |
| Caffeoyl-CoA O-methyltransferase | Q40313 | CAMT_MEDSA | Medicago sativa | 3 | 0.7633 |
| Caffeoyl-CoA O-methyltransferase | Q40313 | CAMT_MEDSA | Medicago sativa | 3 | 0.7633 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7450 |
| Pentaerythritol tetranitrate reductase | P71278 | P71278_ENTCL | Enterobacter cloacae | 2 | 0.7450 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7367 |
| NADPH-dependent oxidoreductase 2-alkenal reductase | Q39172 | AER_ARATH | Arabidopsis thaliana | 2 | 0.7367 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7188 |
| Single-stranded-DNA-specific exonuclease RecJ | D0EM60 | D0EM60_DEIRD | Deinococcus radiodurans | 2 | 0.7188 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7114 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7114 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.7098 |
| Adenosine 5'-monophosphoramidase HINT1 | P80912 | HINT1_RABIT | Oryctolagus cuniculus | 3 | 0.7098 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7053 |
| Collagenase 3 | P45452 | MMP13_HUMAN | Homo sapiens | 3 | 0.7053 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7044 |
| Carbonic anhydrase 4 | Q64444 | CAH4_MOUSE | Mus musculus | 2 | 0.7044 |
| Penicillin V acylase | P12256 | PAC_LYSSH | Lysinibacillus sphaericus | 3 | 0.7015 |
| Penicillin V acylase | P12256 | PAC_LYSSH | Lysinibacillus sphaericus | 3 | 0.7015 |