Kaempferol-3-O-(6''-O-acetyl)-beta-D-glucopyranoside - Compound Card

Kaempferol-3-O-(6''-O-acetyl)-beta-D-glucopyranoside

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Kaempferol-3-O-(6''-O-acetyl)-beta-D-glucopyranoside

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonol Glycoside
Canonical Smiles CC(=O)OC[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/C23H22O12/c1-9(24)32-8-15-17(28)19(30)20(31)23(34-15)35-22-18(29)16-13(27)6-12(26)7-14(16)33-21(22)10-2-4-11(25)5-3-10/h2-7,15,17,19-20,23,25-28,30-31H,8H2,1H3/t15-,17-,19+,20-,23+/m1/s1
InChIKey AKENCGNASJPQNR-LNNZMUSMSA-N
Formula C23H22O12
HBA 12
HBD 6
MW 490.42
Rotatable Bonds 5
TPSA 196.35
LogP 0.33
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 490.11
Number of Lipinski Rule Violations 2
# Species Family Kingdom NCBI Taxonomy ID
1 Chiliadenus montanus Asteraceae Plantae 1458965

Showing of synonyms

  • Hegazy MEF, Matsuda H, et al. (2014). Chemical constituents and their antibacterial and antifungal activity from the Egyptian herbal medicine Chiliadenus montanus. Phytochemistry,2014,103,154-161. [View] [PubMed]
Pubchem: 10435673
Nmrshiftdb2: 60024874

No compound-protein relationship available.

Structure

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

Level: 2

Mol. Weight: 490.42 g/mol

Structure

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

Level: 1

Mol. Weight: 490.42 g/mol

Structure

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

Level: 1

Mol. Weight: 490.42 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 490.42 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 490.42 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 490.42 g/mol

Antimicrobial

Absorption

Caco-2 (logPapp)
-6.82
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.14
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
0.79

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.95
Plasma Protein Binding
78.64
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
13.46
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.16
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.19
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.37
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
-269.87
Rat (Acute)
2.34
Rat (Chronic Oral)
3.97
Fathead Minnow
4.11
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
616.1
Hydration Free Energy
-3.85
Log(D) at pH=7.4
0.82
Log(P)
1.31
Log S
-4.41
Log(Vapor Pressure)
-11.2
Melting Point
197.11
pKa Acid
5.68
pKa Basic
5.71
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9777
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9777
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9310
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9310
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9128
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9128
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9050
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.9050
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8917
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8917
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8904
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8904
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8784
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8784
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8723
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8723
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8618
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8618
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8528
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8528
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8488
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8488
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8431
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8431
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8415
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8415
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8412
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8412
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8409
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8409
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8371
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8371
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8367
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.8367
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8284
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8284
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8284
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8284
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8227
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.8227
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8220
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8220
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8210
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8210
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8147
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.8147
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8093
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8093
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8087
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8087
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8084
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.8084
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8056
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8056
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8044
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8044
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8024
Avidin P02701 AVID_CHICK Gallus gallus 3 0.8024
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7952
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7952
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7930
RNA-dependent RNA polymerase Q6A562 Q6A562_9VIRU Thosea asigna virus 3 0.7930
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7894
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7894
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7842
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7842
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7822
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7822
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7822
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7822
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7802
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7802
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7790
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7790
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7774
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7774
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7762
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7762
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7741
Beta-glucuronidase P05804 BGLR_ECOLI Escherichia coli 3 0.7741
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7730
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7730
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7700
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7700
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7689
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7689
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.7670
Multidrug efflux pump subunit AcrB P31224 ACRB_ECOLI Escherichia coli 4 0.7670
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7654
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7654
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7643
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7643
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7623
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7623
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7586
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7586
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7573
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7573
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7571
Streptogramin A acetyltransferase P50870 VATD_ENTFC Enterococcus faecium 3 0.7571
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7516
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7516
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7477
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7477
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7476
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7476
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7410
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7410
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7403
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7403
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7386
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7386
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 4 0.7369
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 4 0.7369
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7326
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 3 0.7326
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7311
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7311
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7285
Periplasmic pH-dependent serine endoprotease DegQ P39099 DEGQ_ECOLI Escherichia coli 4 0.7285
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7262
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.7262
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7249
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7249
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7244
3-hydroxyanthranilate 3,4-dioxygenase Q1LCS4 3HAO_CUPMC Cupriavidus metallidurans 2 0.7244
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7211
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7211
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7174
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7174
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7168
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7168
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7148
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7148
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7122
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7122
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7113
Beta-hexosaminidase Q9KU37 NAGZ_VIBCH Vibrio cholerae serotype O1 3 0.7113
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7102
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7102
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7090
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7090
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7088
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha P49354 FNTA_HUMAN Homo sapiens 3 0.7088
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7081
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7081
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7081
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7081
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7073
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7073
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7043
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7043
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7034
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7034
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7026
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7026
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7025
DNA gyrase subunit B Q839Z1 GYRB_ENTFA Enterococcus faecalis 3 0.7025
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7007
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7007
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 4 0.7007
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7007
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7001
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7001

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