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Kaempherol-3-O-glucoside
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
Canonical Smiles | OC[C@@H]1OC(Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@H]([C@@H]([C@H]1O)O)O |
---|---|
InChI | InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21?/m0/s1 |
InChIKey | JPUKWEQWGBDDQB-NCHJZECQSA-N |
Formula | C21H20O11 |
HBA | 11 |
HBD | 7 |
MW | 448.38 |
Rotatable Bonds | 4 |
TPSA | 190.28 |
LogP | -0.24 |
Number Rings | 4 |
Number Aromatic Rings | 3 |
Heavy Atom Count | 32 |
Formal Charge | 0 |
Fraction CSP3 | 0.29 |
Exact Mass | 448.1 |
Number of Lipinski Rule Violations | 2 |
# | Species | Family | Kingdom | NCBI Taxonomy ID |
---|---|---|---|---|
1 | Crataegus azarolus | Rosaceae | Plantae | 298644 |
2 | Crataegus monogyna | Rosaceae | Plantae | 140997 |
Showing of synonyms
Kaempherol-3-O-glucoside
- Mraihi F, Hidalgo M, et al. (2015). Wild grown red and yellow hawthorn fruits from Tunisia as source of antioxidants. Arabian Journal of Chemistry, 2015, 8(4), 570-578. [View]
Pubchem:
133564575
No compound-protein relationship available.
SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4
Level: 2
Mol. Weight: 448.38 g/mol
SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3
Level: 1
Mol. Weight: 448.38 g/mol
SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3
Level: 1
Mol. Weight: 448.38 g/mol
SMILES: c1cccc(c12)occc2=O
Level: 0
Mol. Weight: 448.38 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 448.38 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 448.38 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.33
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.54
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- 1.73
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.9
- Plasma Protein Binding
- 78.33
- 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
- 11.64
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Toxic
- Avian
- Safe
- Bee
- Safe
- Bioconcentration Factor
- -1.84
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 1.08
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 4.6
- 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
- -73.75
- Rat (Acute)
- 2.42
- Rat (Chronic Oral)
- 3.74
- Fathead Minnow
- 3.94
- 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
- 603.87
- Hydration Free Energy
- -5.35
- Log(D) at pH=7.4
- 0.38
- Log(P)
- 1.0
- Log S
- -4.18
- Log(Vapor Pressure)
- -11.38
- Melting Point
- 211.37
- pKa Acid
- 5.77
- pKa Basic
- 7.08
Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
---|---|---|---|---|---|
Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.9468 |
Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 5 | 0.9207 |
Ribosyldihydronicotinamide dehydrogenase [quinone] | P16083 | NQO2_HUMAN | Homo sapiens | 4 | 0.9052 |
Tyrosine-protein kinase JAK3 | P52333 | JAK3_HUMAN | Homo sapiens | 3 | 0.8987 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.8930 |
Casein kinase II subunit alpha | P68400 | CSK21_HUMAN | Homo sapiens | 4 | 0.8841 |
Bromodomain-containing protein 2 | P25440 | BRD2_HUMAN | Homo sapiens | 3 | 0.8821 |
Nodulin-13 | P93330 | NOD13_MEDTR | Medicago truncatula | 3 | 0.8809 |
Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.8592 |
Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8573 |
Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.8512 |
Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.8494 |
Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 6 | 0.8388 |
Serine/threonine-protein kinase pim-1 | P11309 | PIM1_HUMAN | Homo sapiens | 3 | 0.8343 |
D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8171 |
Rhodopsin kinase GRK1 | P28327 | GRK1_BOVIN | Bos taurus | 3 | 0.8119 |
Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.8007 |
Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7983 |
Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7979 |
Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7958 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7916 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7848 |
HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.7836 |
Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7784 |
Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7753 |
Major pollen allergen Bet v 1-A | P15494 | BEV1A_BETPN | Betula pendula | 3 | 0.7740 |
Polyprotein | Q80J95 | Q80J95_9CALI | Murine norovirus 1 | 3 | 0.7720 |
Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 3 | 0.7715 |
Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7699 |
Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7643 |
Transcriptional regulator, PadR-like family | A2RI36 | A2RI36_LACLM | Lactococcus lactis subsp. cremoris | 3 | 0.7639 |
FMN-dependent NAD(P)H:quinone oxidoreductase 1 | Q9I5F3 | AZOR1_PSEAE | Pseudomonas aeruginosa | 3 | 0.7568 |
Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 2 | 0.7554 |
S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7548 |
Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7533 |
Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7523 |
Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7509 |
Queuine tRNA-ribosyltransferase | P28720 | TGT_ZYMMO | Zymomonas mobilis subsp. mobilis | 3 | 0.7495 |
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform | O02697 | PK3CG_PIG | Sus scrofa | 5 | 0.7494 |
Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7465 |
Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7414 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7379 |
3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7373 |
Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 2 | 0.7363 |
O-methyltransferase family 2 | D5STZ7 | D5STZ7_PLAL2 | Planctopirus limnophila | 4 | 0.7332 |
Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7300 |
Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7299 |
Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.7272 |
Prothrombin | P00734 | THRB_HUMAN | Homo sapiens | 3 | 0.7233 |
Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 3 | 0.7231 |
Glucan 1,3-beta-glucosidase | P29717 | EXG1_CANAL | Candida albicans | 3 | 0.7213 |
Gag-Pol polyprotein | P05896 | POL_SIVM1 | Simian immunodeficiency virus | 3 | 0.7212 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7210 |
CCR4-NOT transcription complex subunit 6-like | Q96LI5 | CNO6L_HUMAN | Homo sapiens | 4 | 0.7199 |
Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7193 |
Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.7185 |
Serine/threonine-protein kinase RAD53 | P22216 | RAD53_YEAST | Saccharomyces cerevisiae | 4 | 0.7183 |
Putative protease I | Q8A8A4 | Q8A8A4_BACTN | Bacteroides thetaiotaomicron | 3 | 0.7154 |
17beta-hydroxysteroid dehydrogenase | O93874 | O93874_COCLU | Cochliobolus lunatus | 3 | 0.7154 |
Beta-hexosaminidase | Q9KU37 | NAGZ_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7119 |
Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7091 |
Serine/threonine-protein kinase PLK1 | P53350 | PLK1_HUMAN | Homo sapiens | 3 | 0.7089 |
Flavin reductase (NADPH) | P30043 | BLVRB_HUMAN | Homo sapiens | 3 | 0.7083 |
Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7079 |
Ribosomal protein S6 kinase alpha-3 | P18654 | KS6A3_MOUSE | Mus musculus | 7 | 0.7070 |
Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 2 | 0.7058 |
4-hydroxyphenylacetate 3-monooxygenase | Q8YHT7 | Q8YHT7_BRUME | Brucella melitensis biotype 1 | 2 | 0.7054 |
Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.7030 |
Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 2 | 0.7021 |
Beta-lactamase | Q9L5C8 | Q9L5C8_ECOLX | Escherichia coli | 3 | 0.7017 |
HTH-type transcriptional regulator QacR | P0A0N4 | QACR_STAAU | Staphylococcus aureus | 3 | 0.7008 |
Botulinum neurotoxin type A | P0DPI0 | BXA1_CLOBO | Clostridium botulinum | 3 | 0.7007 |