Kaempferol 3-O-glucuronide - Compound Card

Kaempferol 3-O-glucuronide

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Kaempferol 3-O-glucuronide

Structure
Zoomed Structure
  • Family: Plantae - Onagraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@@H]1O[C@H](C(=O)O)[C@H](C(C1O)O)O)O
InChI InChI=1S/C21H18O12/c22-8-3-1-7(2-4-8)17-18(13(25)12-10(24)5-9(23)6-11(12)31-17)32-21-16(28)14(26)15(27)19(33-21)20(29)30/h1-6,14-16,19,21-24,26-28H,(H,29,30)/t14?,15-,16?,19-,21+/m0/s1
InChIKey FNTJVYCFNVUBOL-ROQVLGAUSA-N
Formula C21H18O12
HBA 11
HBD 7
MW 462.36
Rotatable Bonds 4
TPSA 207.35
LogP -0.15
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 33
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 462.08
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Epilobium hirsutum Onagraceae Plantae 210355

Showing of synonyms

  • Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]
Pubchem: 44258914

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 462.36 g/mol

Structure

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

Level: 1

Mol. Weight: 462.36 g/mol

Structure

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

Level: 1

Mol. Weight: 462.36 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 462.36 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 462.36 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 462.36 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.93
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.510
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
1.08

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.010
Plasma Protein Binding
72.75
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
10.240
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.670
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
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
5.160
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
-102.320
Rat (Acute)
2.260
Rat (Chronic Oral)
4.270
Fathead Minnow
4.020
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
637.200
Hydration Free Energy
-4.600
Log(D) at pH=7.4
-1.110
Log(P)
1.19
Log S
-3.87
Log(Vapor Pressure)
-12.28
Melting Point
218.7
pKa Acid
3.96
pKa Basic
6.91
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9766
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9766
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9444
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9444
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9140
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9140
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8991
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8991
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8871
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8871
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8841
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8841
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8536
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8536
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8480
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8480
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8386
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8386
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8243
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8243
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8192
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8192
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8101
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8101
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8089
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8089
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8051
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8051
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8046
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8046
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7943
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7943
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7943
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7943
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7831
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7831
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7822
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7822
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7770
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7770
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7750
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7750
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7720
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7720
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 3 0.7702
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 3 0.7702
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7620
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7620
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7598
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7598
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.7575
ADP-ribosyl-[dinitrogen reductase] hydrolase A7XNI2 A7XNI2_AZOBR Azospirillum brasilense 3 0.7575
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7529
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7529
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7437
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 3 0.7437
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7424
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7424
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7405
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7405
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7359
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7359
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7349
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7349
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7303
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7303
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7297
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7297
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7265
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7265
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7233
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7233
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7221
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 3 0.7221
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7220
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7220
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7213
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7213
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7183
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7183
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7174
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7174
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7146
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7146
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7131
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7131
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7130
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7130
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7123
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7123
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7109
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7109
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7092
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7092
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7058
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7058
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7049
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7049
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7032
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7032
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7015
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7015

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