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Alizarin 1-methyl ether 2-O-primeveroside (ruberythric acid 1-methyl ether)
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
- Class: Anthraquinone
| Canonical Smiles | COc1c(ccc2c1C(=O)c1ccccc1C2=O)O[C@H]1O[C@@H](COC2OC[C@@H]([C@H]([C@@H]2O)O)O)[C@@H]([C@H]([C@@H]1O)O)O |
|---|---|
| InChI | InChI=1S/C26H28O13/c1-35-24-14(7-6-12-16(24)18(29)11-5-3-2-4-10(11)17(12)28)38-26-23(34)21(32)20(31)15(39-26)9-37-25-22(33)19(30)13(27)8-36-25/h2-7,13,15,19-23,25-27,30-34H,8-9H2,1H3/t13-,15-,19+,20-,21+,22-,23-,25?,26-/m0/s1 |
| InChIKey | IKXUYXBMZZLWRY-BBGWUZQQSA-N |
| Formula | C26H28O13 |
| HBA | 13 |
| HBD | 6 |
| MW | 548.5 |
| Rotatable Bonds | 6 |
| TPSA | 201.67 |
| LogP | -1.89 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 39 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.46 |
| Exact Mass | 548.15 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Galium sinaicum | Rubiaceae | Plantae | 25168 |
Showing of synonyms
Alizarin 1-methyl ether 2-O-primeveroside (ruberythric acid 1-methyl ether)
No compound-protein relationship available.
SMILES: O1CCCCC1OCC2CCCC(O2)Oc(c3)ccc(c34)C(=O)c5c(C4=O)cccc5
Level: 2
Mol. Weight: 548.5 g/mol
SMILES: c1cccc(C2=O)c1C(=O)c(c23)ccc(c3)OC4CCCCO4
Level: 1
Mol. Weight: 548.5 g/mol
SMILES: O1CCCCC1COC2CCCCO2
Level: 1
Mol. Weight: 548.5 g/mol
SMILES: c1cccc(c12)C(=O)c3c(C2=O)cccc3
Level: 0
Mol. Weight: 548.5 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 548.5 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.35
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -4.890
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 0.68
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.910
- Plasma Protein Binding
- 85.49
- 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
- Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 5.470
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -2.800
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.860
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.960
- 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
- -2959.320
- Rat (Acute)
- 2.790
- Rat (Chronic Oral)
- 4.040
- Fathead Minnow
- 8.370
- 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
- 532.810
- Hydration Free Energy
- -2.920
- Log(D) at pH=7.4
- -0.060
- Log(P)
- -0.46
- Log S
- -3.41
- Log(Vapor Pressure)
- -11.94
- Melting Point
- 194.05
- pKa Acid
- 3.37
- pKa Basic
- 3.99
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.9309 |
| Cholinesterase | P06276 | CHLE_HUMAN | Homo sapiens | 3 | 0.8734 |
| Alpha-ketoglutarate-dependent dioxygenase FTO | Q9C0B1 | FTO_HUMAN | Homo sapiens | 3 | 0.8525 |
| Cytohesin-2 | Q99418 | CYH2_HUMAN | Homo sapiens | 3 | 0.8262 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8225 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8135 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7933 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7879 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 2 | 0.7876 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7840 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 2 | 0.7837 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7819 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7731 |
| Lactoperoxidase | A0A452E9Y6 | PERL_CAPHI | Capra hircus | 2 | 0.7572 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7550 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7532 |
| ATP-dependent molecular chaperone HSP82 | P02829 | HSP82_YEAST | Saccharomyces cerevisiae | 2 | 0.7506 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9Y233 | PDE10_HUMAN | Homo sapiens | 3 | 0.7500 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7494 |
| Photosynthetic reaction center cytochrome c subunit | P07173 | CYCR_BLAVI | Blastochloris viridis | 3 | 0.7489 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7443 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7439 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7425 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7422 |
| Dipeptidyl peptidase 4 | P27487 | DPP4_HUMAN | Homo sapiens | 3 | 0.7421 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 2 | 0.7419 |
| Tetracycline repressor protein class B from transposon Tn10 | P04483 | TETR2_ECOLX | Escherichia coli | 3 | 0.7354 |
| Squalene synthase | P37268 | FDFT_HUMAN | Homo sapiens | 3 | 0.7353 |
| Chymotrypsinogen A | P00766 | CTRA_BOVIN | Bos taurus | 3 | 0.7343 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 2 | 0.7332 |
| Casein kinase II subunit alpha | P28523 | CSK2A_MAIZE | Zea mays | 3 | 0.7327 |
| Acetyl-CoA carboxylase | Q00955 | ACAC_YEAST | Saccharomyces cerevisiae | 3 | 0.7313 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7297 |
| Angiotensin-converting enzyme 2 | Q9BYF1 | ACE2_HUMAN | Homo sapiens | 2 | 0.7252 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7190 |
| F420-dependent methylenetetrahydromethanopterin dehydrogenase | P94951 | MTD_METKA | Methanopyrus kandleri | 2 | 0.7176 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7173 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7161 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.7132 |
| Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial | Q8N5Z0 | AADAT_HUMAN | Homo sapiens | 2 | 0.7117 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7114 |
| Carbonyl reductase [NADPH] 1 | P16152 | CBR1_HUMAN | Homo sapiens | 2 | 0.7111 |
| Aurora kinase A | O14965 | AURKA_HUMAN | Homo sapiens | 2 | 0.7088 |
| Lactoperoxidase | P80025 | PERL_BOVIN | Bos taurus | 2 | 0.7087 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 2 | 0.7047 |
| Fibroblast growth factor receptor 1 | P11362 | FGFR1_HUMAN | Homo sapiens | 3 | 0.7033 |
| Tyrosine-protein kinase Lck | P06239 | LCK_HUMAN | Homo sapiens | 3 | 0.7017 |
| D-alanyl-D-alanine carboxypeptidase | P15555 | DAC_STRSR | Streptomyces sp | 2 | 0.7000 |