Kaempferol-3-rhamnoside - Compound Card

Kaempferol-3-rhamnoside

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Kaempferol-3-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Canellaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1O[C@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)[O-]
InChI InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/p-1/t8-,15-,17+,18+,21+/m0/s1
InChIKey SOSLMHZOJATCCP-MKMJNHTISA-M
Formula C21H19O10-
HBA 10
HBD 5
MW 431.37
Rotatable Bonds 3
TPSA 172.88
LogP 0.15
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge -1
Fraction CSP3 0.29
Exact Mass 431.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Chenopodium murale Chenopodiaceae Plantae 46091
2 Ephedra alata Ephedraceae Plantae 302006
3 Silybum marianum Asteraceae Plantae 92921
4 Warburgia ugandensis Canellaceae Plantae 549619

Showing of synonyms

  • El-Sayed NH, Awaad AS, et al. (1999). A flavonol triglycoside from Chenopodium murale. Phytochemistry,1999,51(4),591-593. [View]
  • Nawwar MAM, El-Sissi HI, et al. (1984). Flavonoid constituents of Ephedra alata. Phytochemistry,1984,23(12),2937-2939. [View]
  • Ahmed AA, Marry TJ, et al. (1989). Flavonoids of the flowers of Silybum marianum. Phytochemistry,1989,28(6),1751-1753. [View]
  • Manguro LO, Ugi I, et al. (2003). Flavonol glycosides of Warburgia ugandensis leaves. Phytochemistry,2003,64(4),891-896. [View] [PubMed]
Pubchem: 25202794
CPRiL: 55857
Structure

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

Level: 2

Mol. Weight: 431.37 g/mol

Structure

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

Level: 1

Mol. Weight: 431.37 g/mol

Structure

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

Level: 1

Mol. Weight: 431.37 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 431.37 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 431.37 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 431.37 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.7
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.110
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.45

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.160
Plasma Protein Binding
98.33
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
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
12.560
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.760
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.290
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.200
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-42.070
Rat (Acute)
2.430
Rat (Chronic Oral)
3.610
Fathead Minnow
4.060
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
561.400
Hydration Free Energy
-6.550
Log(D) at pH=7.4
0.530
Log(P)
0.79
Log S
-4.04
Log(Vapor Pressure)
-11.61
Melting Point
230.6
pKa Acid
5.91
pKa Basic
4.51
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9749
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9749
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9477
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9477
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9323
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9323
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9198
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9198
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8964
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8964
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8913
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8913
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8894
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8894
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8887
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8887
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8755
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8755
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8650
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8650
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8614
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8614
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8578
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8578
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8363
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8363
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8310
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8310
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8302
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8302
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8281
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8281
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8267
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8267
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8210
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8210
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8188
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8188
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.8155
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.8155
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8086
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8086
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8040
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8040
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7907
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7907
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7888
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7888
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7828
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7828
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7801
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7801
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7791
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7791
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 3 0.7785
Glycoside Hydrolase Family 13 Q65MI2 Q65MI2_BACLD Bacillus licheniformis 3 0.7785
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7767
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7767
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7762
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7762
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7718
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7718
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7631
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7631
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7622
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.7622
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7550
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7550
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7497
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7497
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7469
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7469
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7455
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7455
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7362
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7362
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7352
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7352
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7312
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 3 0.7312
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7310
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7310
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7282
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7282
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7240
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7240
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7230
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7230
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7226
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7226
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 5 0.7215
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 5 0.7215
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7209
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7209
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7205
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7205
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7176
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7176
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.7151
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.7151
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7135
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7135
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7122
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7122
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7115
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.7115
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7086
Vitamin D-binding protein P02774 VTDB_HUMAN Homo sapiens 2 0.7086
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7076
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.7076
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7046
Small heat shock protein StHsp14.0 Q970D9 Q970D9_SULTO Sulfurisphaera tokodaii 3 0.7046
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7039
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7036
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7036
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7035
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7035
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7029
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7029
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7025
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7025
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7008
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7008
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7005
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7005
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7005
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7005

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