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Kaempferol-3-O-alpha-L-rhamnoside
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonol Glycoside
| Canonical Smiles | Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O |
|---|---|
| InChI | InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21+/m0/s1 |
| InChIKey | SOSLMHZOJATCCP-MKMJNHTISA-N |
| Formula | C21H20O10 |
| HBA | 10 |
| HBD | 6 |
| MW | 432.38 |
| Rotatable Bonds | 3 |
| TPSA | 170.05 |
| LogP | 0.78 |
| Number Rings | 4 |
| Number Aromatic Rings | 3 |
| Heavy Atom Count | 31 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.29 |
| Exact Mass | 432.11 |
| Number of Lipinski Rule Violations | 1 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Ixora coccinea | Rubiaceae | Plantae | 43503 |
Showing of synonyms
Kaempferol-3-O-alpha-L-rhamnoside
5,7-Dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
- Idowu TO, Ogundaini AO, et al. (2010). Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry,2010,71(17–18),2092-2098. [View]
CPRiL:
55857
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 432.38 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 432.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 432.38 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 432.38 g/mol
Antibacterial
Absorption
- Caco-2 (logPapp)
- -6.78
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.330
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 0.41
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.970
- Plasma Protein Binding
- 86.54
- 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
- 12.770
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -0.950
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.190
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.260
- 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
- -42.180
- Rat (Acute)
- 2.400
- Rat (Chronic Oral)
- 3.860
- Fathead Minnow
- 3.840
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 588.810
- Hydration Free Energy
- -7.280
- Log(D) at pH=7.4
- 1.030
- Log(P)
- 1.67
- Log S
- -4.28
- Log(Vapor Pressure)
- -11.14
- Melting Point
- 205.55
- pKa Acid
- 5.36
- pKa Basic
- 6.09
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.9749 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9477 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.9323 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9198 |
| ATP synthase subunit alpha, mitochondrial | P19483 | ATPA_BOVIN | Bos taurus | 3 | 0.8964 |
| Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.8913 |
| Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8894 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8887 |
| Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.8755 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8650 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8614 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8578 |
| Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.8363 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.8310 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.8302 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.8281 |
| Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.8267 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 3 | 0.8210 |
| Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8188 |
| Botulinum neurotoxin type A | P0DPI0 | BXA1_CLOBO | Clostridium botulinum | 3 | 0.8155 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8086 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.8040 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7907 |
| Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7888 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7828 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.7801 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7791 |
| Glycoside Hydrolase Family 13 | Q65MI2 | Q65MI2_BACLD | Bacillus licheniformis | 3 | 0.7785 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7767 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7762 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7718 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7631 |
| Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.7622 |
| Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7550 |
| Cytochrome P450 1A1 | P04798 | CP1A1_HUMAN | Homo sapiens | 3 | 0.7497 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7469 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7455 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 5 | 0.7362 |
| Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase | Q9TQS6 | DHDH_MACFA | Macaca fascicularis | 3 | 0.7352 |
| 17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7312 |
| Mitogen-activated protein kinase 8 | P45983 | MK08_HUMAN | Homo sapiens | 3 | 0.7310 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7282 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7240 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7230 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7226 |
| Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 5 | 0.7215 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7209 |
| Avidin | P02701 | AVID_CHICK | Gallus gallus | 3 | 0.7205 |
| Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7176 |
| Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 7 | 0.7151 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7135 |
| 3-phosphoinositide-dependent protein kinase 1 | O15530 | PDPK1_HUMAN | Homo sapiens | 3 | 0.7122 |
| Pancreatic alpha-amylase | P04746 | AMYP_HUMAN | Homo sapiens | 3 | 0.7115 |
| Vitamin D-binding protein | P02774 | VTDB_HUMAN | Homo sapiens | 2 | 0.7086 |
| cAMP-dependent protein kinase catalytic subunit alpha | P00517 | KAPCA_BOVIN | Bos taurus | 4 | 0.7076 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7046 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7039 |
| CREB-binding protein | Q92793 | CBP_HUMAN | Homo sapiens | 3 | 0.7036 |
| Orf1a polyprotein | Q692E5 | Q692E5_CVHSA | SARS coronavirus TJF | 2 | 0.7035 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7029 |
| Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7025 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7008 |
| Genome polyprotein | O92972 | POLG_HCVJ4 | Hepatitis C virus genotype 1b | 3 | 0.7005 |
| Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7005 |