Kaempferol 3-O-beta-D-glucopyranoside - Compound Card

Kaempferol 3-O-beta-D-glucopyranoside

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Kaempferol 3-O-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles OCC1O[C@@H](Oc2c(oc3c(c2=O)c(O)cc(c3)O)c2ccc(cc2)O)[C@H](C([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+/m1/s1
InChIKey JPUKWEQWGBDDQB-OBLDEXFVSA-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 Carissa edulis Apocynaceae Plantae 992661

Showing of synonyms

  • Al-Youssef HM and Hassan WHB. (2014). Chemical constituents of Carissa edulis Vahl. Arabian Journal of Chemistry,2014,in press. [View]
Pubchem: 89719004
Nmrshiftdb2: 70052202
CPRiL: 60247
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)
-6.31
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
75.08
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
11.63
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.68
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.08
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.61
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
-73.45
Rat (Acute)
2.42
Rat (Chronic Oral)
3.74
Fathead Minnow
3.97
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
601.77
Hydration Free Energy
-5.35
Log(D) at pH=7.4
0.39
Log(P)
0.99
Log S
-4.14
Log(Vapor Pressure)
-11.23
Melting Point
208.45
pKa Acid
5.78
pKa Basic
7.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9443
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9443
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9110
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9110
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9063
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9063
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8977
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8977
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8898
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8898
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8876
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8876
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8803
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8803
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8791
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8791
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8684
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.8684
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8603
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8603
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8502
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8502
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8467
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8467
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8444
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8444
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8228
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8228
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8211
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8211
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8181
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8181
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8135
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8135
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8106
Maltose/maltodextrin-binding periplasmic protein P0AEX9 MALE_ECOLI Escherichia coli 3 0.8106
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8093
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8093
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8058
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8058
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8043
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8043
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8010
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8010
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8009
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8009
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7956
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 3 0.7956
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7929
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7929
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7929
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7929
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7928
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7928
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7921
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7921
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7873
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7873
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7871
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7871
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
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7771
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7771
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7740
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 4 0.7740
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7720
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7720
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7717
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7717
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7713
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7713
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7688
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7688
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7675
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7675
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7641
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7641
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7577
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7577
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7571
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.7571
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7567
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7567
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7564
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7564
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7534
Tannase B3Y018 B3Y018_LACPN Lactiplantibacillus plantarum 4 0.7534
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7531
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7531
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7514
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7514
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7499
Cyclic dipeptide N-prenyltransferase D1D8L6 D1D8L6_ASPFM Neosartorya fumigata 3 0.7499
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7480
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7480
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7356
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7356
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7344
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7344
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7327
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7327
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7326
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7326
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7300
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7300
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7289
FMN-dependent NAD(P)H:quinone oxidoreductase 1 Q9I5F3 AZOR1_PSEAE Pseudomonas aeruginosa 2 0.7289
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7275
Methylmalonyl-CoA decarboxylase P52045 SCPB_ECOLI Escherichia coli 3 0.7275
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7274
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7274
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7256
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7256
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7236
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7236
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7234
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7234
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7229
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7229
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7229
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7229
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7227
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7227
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7213
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7213
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7189
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7189
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7188
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7188
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7158
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7158
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7133
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7133
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7123
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7123
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7095
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 4 0.7095
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7090
L-lactate dehydrogenase A chain P13491 LDHA_RABIT Oryctolagus cuniculus 2 0.7090
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7078
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7078
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7070
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7070
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7063
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7063
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7045
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7045
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7045
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7045
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7035
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7035
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7035
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7035
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7031
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7031
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7005
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7005
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7004
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7004

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