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3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2-methoxyphenoxy]propyl-beta-D-glucopyranoside
- Family: Plantae - Acanthaceae
- Kingdom: Plantae
-
Class: Phenolic
- Subclass: Phenolic Glycoside
| Canonical Smiles | OCC=Cc1ccc(c(c1)OC)OC(C(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/t20-,21?,22-,23+,24-,25?,26+/m1/s1 |
| InChIKey | MNLWSKFTELUKMW-VTIZYCQHSA-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 | Ruellia tuberosa | Acanthaceae | Plantae | 441035 |
Showing of synonyms
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxy-1-(E)-propenyl)-2-methoxyphenoxy]propyl-beta-D-glucopyranoside
- Samy MN, Khalil HE, et al. (2013). Chemical constituents from the leaves of Ruellia tuberosa. Chemistry of Natural Compounds,2013,49(1),175-176. [View]
Pubchem:
91321267
No compound-protein relationship available.
SMILES: O1CCCCC1OC(c2ccccc2)COc3ccccc3
Level: 2
Mol. Weight: 538.55 g/mol
SMILES: c1ccccc1OCCOC2CCCCO2
Level: 1
Mol. Weight: 538.55 g/mol
SMILES: c1ccccc1CCOc2ccccc2
Level: 1
Mol. Weight: 538.55 g/mol
SMILES: c1ccccc1COC2CCCCO2
Level: 1
Mol. Weight: 538.55 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 538.55 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 538.55 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.17
- 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
- 51.31
- 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
- 9.65
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -2.19
- 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
- Safe
- Daphnia Maga
- 5.96
- 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
- -1228.16
- Rat (Acute)
- 2.38
- Rat (Chronic Oral)
- 4.1
- Fathead Minnow
- 4.83
- 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
- 524.07
- Hydration Free Energy
- -2.93
- Log(D) at pH=7.4
- 0.67
- Log(P)
- -0.85
- Log S
- -3.65
- Log(Vapor Pressure)
- -10.7
- Melting Point
- 164.29
- pKa Acid
- 5.3
- pKa Basic
- 3.03
| 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 | 0.9332 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.9332 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.9181 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.9181 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9125 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.9125 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8643 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8643 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8548 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8548 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8527 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8527 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8384 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8384 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8384 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.8384 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8376 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8376 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8244 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8244 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8229 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8229 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.8219 |
| Genome polyprotein | P26663 | POLG_HCVBK | Hepatitis C virus genotype 1b | 3 | 0.8219 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8091 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8091 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8069 |
| NAD-capped RNA hydrolase NudC | P32664 | NUDC_ECOLI | Escherichia coli | 3 | 0.8069 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8067 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8067 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8007 |
| Serpin domain-containing protein | H0ZQY2 | H0ZQY2_TAEGU | Taeniopygia guttata | 3 | 0.8007 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7978 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7978 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7957 |
| Liver carboxylesterase 1 | P23141 | EST1_HUMAN | Homo sapiens | 3 | 0.7957 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7947 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7947 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 4 | 0.7904 |
| Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 4 | 0.7904 |
| Caspase-3 | P42574 | CASP3_HUMAN | Homo sapiens | 3 | 0.7860 |
| Caspase-3 | P42574 | CASP3_HUMAN | Homo sapiens | 3 | 0.7860 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7785 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7785 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7729 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7729 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7723 |
| Carbonic anhydrase 1 | P00915 | CAH1_HUMAN | Homo sapiens | 3 | 0.7723 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7629 |
| N-alpha-acetyltransferase 50 | Q9GZZ1 | NAA50_HUMAN | Homo sapiens | 3 | 0.7629 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7564 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 3 | 0.7564 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7562 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7562 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7518 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7518 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7510 |
| Hypoxanthine phosphoribosyltransferase | Q4DRC4 | Q4DRC4_TRYCC | Trypanosoma cruzi | 3 | 0.7510 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7499 |
| Peptidyl-prolyl cis-trans isomerase FKBP1A | P62942 | FKB1A_HUMAN | Homo sapiens | 3 | 0.7499 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7487 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7487 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7432 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7432 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7430 |
| Protein ppBat | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron VPI-5482 | 3 | 0.7430 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7417 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7417 |
| Virulence sensor histidine kinase PhoQ | P0DM80 | PHOQ_SALTY | Salmonella typhimurium | 4 | 0.7416 |
| Virulence sensor histidine kinase PhoQ | P0DM80 | PHOQ_SALTY | Salmonella typhimurium | 4 | 0.7416 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7401 |
| UDP-galactopyranose mutase | Q48485 | GLF1_KLEPN | Klebsiella pneumoniae | 3 | 0.7401 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7384 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7384 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7380 |
| Seminal ribonuclease | P00669 | RNS_BOVIN | Bos taurus | 3 | 0.7380 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7374 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.7374 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7349 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7349 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7317 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7317 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7308 |
| Chitinase | Q54276 | Q54276_SERMA | Serratia marcescens | 3 | 0.7308 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7300 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.7300 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7292 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7292 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7256 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7256 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7248 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.7248 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7244 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7244 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7215 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7215 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7187 |
| Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 | Q9Y3Z3 | SAMH1_HUMAN | Homo sapiens | 3 | 0.7187 |
| Karilysin | D0EM77 | KLY_TANFA | Tannerella forsythia | 3 | 0.7156 |
| Karilysin | D0EM77 | KLY_TANFA | Tannerella forsythia | 3 | 0.7156 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7147 |
| Oxygenase | Q194P4 | Q194P4_STRAA | Streptomyces argillaceus | 3 | 0.7147 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7144 |
| Thymidylate synthase | P00469 | TYSY_LACCA | Lacticaseibacillus casei | 3 | 0.7144 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7133 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7133 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7130 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7130 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7125 |
| GCN5-related N-acetyltransferase | B1YEL6 | B1YEL6_EXIS2 | Exiguobacterium sibiricum | 3 | 0.7125 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7118 |
| Macrophage metalloelastase | P39900 | MMP12_HUMAN | Homo sapiens | 3 | 0.7118 |
| Calcium/calmodulin-dependent protein kinase type 1D | Q8IU85 | KCC1D_HUMAN | Homo sapiens | 4 | 0.7117 |
| Calcium/calmodulin-dependent protein kinase type 1D | Q8IU85 | KCC1D_HUMAN | Homo sapiens | 4 | 0.7117 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7046 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 3 | 0.7046 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.7026 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.7026 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7010 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7010 |