Kaempherol-3-O-glucoside - Compound Card

Kaempherol-3-O-glucoside

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Kaempherol-3-O-glucoside

Structure
Zoomed Structure
  • 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

  • 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.

Structure

SMILES: c1cccc(c12)oc(-c3ccccc3)c(c2=O)OC4CCCCO4

Level: 2

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)occ(c2=O)OC3CCCCO3

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 448.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 448.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 448.38 g/mol

Structure

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

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