Kaempferol 3-O-(6′′-O-methyl-beta-D-glucuronopyranoside) - Compound Card

Kaempferol 3-O-(6′′-O-methyl-beta-D-glucuronopyranoside)

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Kaempferol 3-O-(6′′-O-methyl-beta-D-glucuronopyranoside)

Structure
Zoomed Structure
  • Family: Plantae - Myrtaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles COC(=O)[C@H]1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O
InChI InChI=1S/C22H20O12/c1-31-21(30)20-16(28)15(27)17(29)22(34-20)33-19-14(26)13-11(25)6-10(24)7-12(13)32-18(19)8-2-4-9(23)5-3-8/h2-7,15-17,20,22-25,27-29H,1H3/t15-,16-,17+,20-,22+/m0/s1
InChIKey MHVNCXOGYHKDBB-NTKSAMNMSA-N
Formula C22H20O12
HBA 12
HBD 6
MW 476.39
Rotatable Bonds 4
TPSA 196.35
LogP -0.06
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 34
Formal Charge 0
Fraction CSP3 0.27
Exact Mass 476.1
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Euphorbia gaditana Euphorbiaceae Plantae 3990
2 Eugenia jambolana Myrtaceae Plantae 260142

Showing of synonyms

  • Mahmoud I.I, Marzouk M.S, et al. (2001). Acylated flavonol glycosides from Eugenia jambolana leaves. Phytochemistry, 2001, 58(8), 1239-44. [View] [PubMed]
  • Badaoui M, Magid A, et al. (2020). Antioxidant activity-guided isolation of constituents from Euphorbia gaditana Coss. and their antioxidant and tyrosinase inhibitory activities. Phytochemistry Letters, 2020, 39, 99-104. [View]
Pubchem: 24788283

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 476.39 g/mol

Structure

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

Level: 1

Mol. Weight: 476.39 g/mol

Structure

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

Level: 1

Mol. Weight: 476.39 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 476.39 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 476.39 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 476.39 g/mol

Antioxidant

Absorption

Caco-2 (logPapp)
-6.74
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.180
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.940
Plasma Protein Binding
77.65
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
13.270
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.890
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.180
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.730
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
-179.820
Rat (Acute)
2.330
Rat (Chronic Oral)
4.190
Fathead Minnow
4.000
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
605.010
Hydration Free Energy
-3.720
Log(D) at pH=7.4
1.110
Log(P)
1.11
Log S
-4.6
Log(Vapor Pressure)
-11.18
Melting Point
197.74
pKa Acid
5.6
pKa Basic
5.19
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9772
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9472
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9196
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9038
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8970
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8922
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8890
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8732
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8690
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8685
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8570
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8547
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8396
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8388
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8373
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8258
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8248
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8242
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.8210
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8183
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8068
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8047
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7994
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7989
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7984
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7976
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7974
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7955
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7919
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7904
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7856
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7844
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7781
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7773
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7766
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7754
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7719
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7670
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 5 0.7652
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7588
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7483
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7482
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7399
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7388
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7316
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7288
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7264
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7234
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7229
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7216
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7184
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7177
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7163
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 2 0.7160
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7143
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7127
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7109
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7107
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7103
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7095
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.7070
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7049
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7030

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