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Rhamnetin-3-O-{[beta-D-apiofuranosyl(1→2)]-[3-hydroxy-3-methyl-glutaroyl(1→6)]}-beta-D-galactopyranoside
- Family: Plantae - Leguminosae/Fabaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Glycoside
| Canonical Smiles | OCC1(O)CO[C@@H]([C@@H]1O)O[C@H]1C(O[C@@H]([C@@H]([C@@H]1O)O)COC(=O)CC(CC(=O)O)(O)C)Oc1c(oc2c(c1=O)c(O)cc(c2)OC)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C33H38O20/c1-32(45,8-20(38)39)9-21(40)48-10-19-23(41)25(43)28(53-31-29(44)33(46,11-34)12-49-31)30(51-19)52-27-24(42)22-17(37)6-14(47-2)7-18(22)50-26(27)13-3-4-15(35)16(36)5-13/h3-7,19,23,25,28-31,34-37,41,43-46H,8-12H2,1-2H3,(H,38,39)/t19-,23+,25+,28-,29+,30?,31-,32?,33?/m1/s1 |
| InChIKey | LBWBQACKWAITFN-LOCSDIGVSA-N |
| Formula | C33H38O20 |
| HBA | 19 |
| HBD | 10 |
| MW | 754.65 |
| Rotatable Bonds | 13 |
| TPSA | 322.03 |
| LogP | -1.6 |
| Number Rings | 5 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 53 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.48 |
| Exact Mass | 754.2 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Astragalus caprinus | Leguminosae/Fabaceae | Plantae | 1042474 |
Showing of synonyms
Rhamnetin-3-O-{[beta-D-apiofuranosyl(1→2)]-[3-hydroxy-3-methyl-glutaroyl(1→6)]}-beta-D-galactopyranoside
- Semmar N, Jay M, et al. (2005). Chemotaxonomic analysis of Astragalus caprinus (Fabaceae) basedon the flavonic patterns. Biochemical Systematics and Ecology, 2005, 33(2), 187-200. [View]
No compound-protein relationship available.
SMILES: O1CCCC1OC2C(OCCC2)Oc(c3=O)c(-c4ccccc4)oc(c35)cccc5
Level: 3
Mol. Weight: 754.65 g/mol
SMILES: O1CCCC1OC2C(OCCC2)Oc(c3=O)coc(c34)cccc4
Level: 2
Mol. Weight: 754.65 g/mol
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 754.65 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 754.65 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 754.65 g/mol
SMILES: O1CCCC1OC2CCCOC2
Level: 1
Mol. Weight: 754.65 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 754.65 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 754.65 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 754.65 g/mol
SMILES: C1CCOC1
Level: 0
Mol. Weight: 754.65 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.57
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -1.37
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 634.07
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.02
- Plasma Protein Binding
- 47.38
- 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
- Inhibitor
Excretion
- Clearance
- 4.94
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -13.29
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.71
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.44
- 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
- -1149073.79
- Rat (Acute)
- 2.24
- Rat (Chronic Oral)
- 4.4
- Fathead Minnow
- 1460.89
- 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
- 121773.16
- Hydration Free Energy
- -2.92
- Log(D) at pH=7.4
- -1.41
- Log(P)
- -0.17
- Log S
- -4.33
- Log(Vapor Pressure)
- -4028.04
- Melting Point
- 182.75
- pKa Acid
- -6.55
- pKa Basic
- 4.0
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9529 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.9468 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.9402 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.9033 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8323 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8303 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.8178 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7831 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7792 |
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.7766 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7729 |
| Acetyl-CoA carboxylase 2 | O00763 | ACACB_HUMAN | Homo sapiens | 4 | 0.7692 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7679 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7668 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 4 | 0.7668 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.7650 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7579 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.7540 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7479 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7428 |
| Tachylectin-2 | Q27084 | TAL2_TACTR | Tachypleus tridentatus | 4 | 0.7335 |
| Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7304 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7275 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7246 |
| Polymerase acidic protein | C3W5S0 | C3W5S0_I09A0 | Influenza A virus | 2 | 0.7238 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 2 | 0.7225 |
| DNA-directed DNA polymerase | Q38087 | DPOL_BPR69 | Escherichia phage RB69 | 3 | 0.7223 |
| Beta-galactoside-specific lectin 4 | Q6ITZ3 | ML4_VISAL | Viscum album | 2 | 0.7215 |
| WxcM-like protein | Q12KT8 | Q12KT8_SHEDO | Shewanella denitrificans | 3 | 0.7211 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7187 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7166 |
| Xylose isomerase | P24300 | XYLA_STRRU | Streptomyces rubiginosus | 3 | 0.7152 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7084 |
| Cyclic GMP-AMP phosphodiesterase SMPDL3A | Q92484 | ASM3A_HUMAN | Homo sapiens | 2 | 0.7065 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7055 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7032 |
| Cysteine synthase | P45040 | CYSK_HAEIN | Haemophilus influenzae | 3 | 0.7032 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7030 |