Kaempferol 3-O-alpha-arabinoside - Compound Card

Kaempferol 3-O-alpha-arabinoside

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Kaempferol 3-O-alpha-arabinoside

Structure
Zoomed Structure
  • Family: Plantae - Euphorbiaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1OC[C@@H]([C@@H]([C@H]1O)O)O)O
InChI InChI=1S/C20H18O10/c21-9-3-1-8(2-4-9)18-19(30-20-17(27)15(25)12(24)7-28-20)16(26)14-11(23)5-10(22)6-13(14)29-18/h1-6,12,15,17,20-25,27H,7H2/t12-,15-,17+,20-/m0/s1
InChIKey RNVUDWOQYYWXBJ-IEGSVRCHSA-N
Formula C20H18O10
HBA 10
HBD 6
MW 418.35
Rotatable Bonds 3
TPSA 170.05
LogP 0.39
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 30
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 418.09
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Opuntia dillenii Cactaceae Plantae 308223
2 Epilobium hirsutum Onagraceae Plantae 210355
3 Warburgia ugandensis Canellaceae Plantae 549619
4 Euphorbia gaditana Euphorbiaceae Plantae 3990

Showing of synonyms

  • Ahmed MS, El Tanbouly ND, et al. (2005). Antiinflammatory flavonoids from Opuntia dillenii (Ker-Gawl) Haw. flowers growing in Egypt.. Phytotherapy Research,2005,19(9),807-809. [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]
  • Manguro LO, Ugi I, et al. (2003). Flavonol glycosides of Warburgia ugandensis leaves. Phytochemistry,2003,64(4),891-896. [View] [PubMed]
  • Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 418.35 g/mol

Structure

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

Level: 1

Mol. Weight: 418.35 g/mol

Structure

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

Level: 1

Mol. Weight: 418.35 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 418.35 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 418.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 418.35 g/mol

Anti-inflammatory
Antioxidant

Absorption

Caco-2 (logPapp)
-6.4
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.410
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.94

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
85.58
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
12.170
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.200
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.110
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.380
Micronucleos
Toxic
NR-AhR
Toxic
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
-28.630
Rat (Acute)
2.430
Rat (Chronic Oral)
3.570
Fathead Minnow
3.950
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
572.940
Hydration Free Energy
-8.810
Log(D) at pH=7.4
0.910
Log(P)
1.35
Log S
-4.2
Log(Vapor Pressure)
-10.58
Melting Point
226.77
pKa Acid
6.37
pKa Basic
6.09
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9439
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9439
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9287
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9287
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9028
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9028
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8930
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8930
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8842
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8842
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8793
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8793
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8786
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8786
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8679
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8679
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8661
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8661
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8622
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8622
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8552
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8552
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8531
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8531
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8528
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8528
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8452
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8452
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8437
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8437
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8270
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8270
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8266
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8266
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8181
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8181
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8176
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8176
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8069
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8069
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8027
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8027
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7988
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7988
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7982
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7982
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7980
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7980
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7968
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7968
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7941
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7941
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7934
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7934
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7917
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7917
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7808
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7808
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7769
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7769
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7760
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7760
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7692
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.7692
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7686
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7686
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7683
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7683
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7647
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7647
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7633
Succinate dehydrogenase [ubiquinone] flavoprotein subunit, mitochondrial Q0QF01 SDHA_PIG Sus scrofa 3 0.7633
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7616
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7616
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7600
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7600
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7522
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7522
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7515
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7515
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7484
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7484
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7478
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7478
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7475
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7475
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7397
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7397
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7389
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7389
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7348
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7348
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7348
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7348
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7315
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7315
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7253
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7253
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7227
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7227
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7200
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7200
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7197
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7197
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7179
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7179
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7166
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7166
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7165
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7165
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7161
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7161
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7157
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7157
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7152
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7152
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7125
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7125
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7119
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7119
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7111
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7111
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7090
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7090
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7090
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7090
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7040
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7040
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7039
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7039
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7034
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7034
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7020
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7020
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7013
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7013
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7004
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7004

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