Kaempferol 3-O-rhamnoside - Compound Card

Kaempferol 3-O-rhamnoside

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Kaempferol 3-O-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Meliaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavonoid Glycoside
Canonical Smiles Oc1ccc(cc1)c1oc2cc(O)cc(c2c(=O)c1OC1O[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/t8-,15-,17+,18+,21?/m1/s1
InChIKey SOSLMHZOJATCCP-VVTWGIOXSA-N
Formula C21H20O10
HBA 10
HBD 6
MW 432.38
Rotatable Bonds 3
TPSA 170.05
LogP 0.78
Number Rings 4
Number Aromatic Rings 3
Heavy Atom Count 31
Formal Charge 0
Fraction CSP3 0.29
Exact Mass 432.11
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Harpephyllum caffrum Anacardiaceae Plantae 289712
2 Melia azedarach Meliaceae Plantae 155640

Showing of synonyms

  • Nawwar M, Hussein S, et al. (2011). Constitutive phenolics of Harpephyllum caffrum (Anacardiaceae) and their biological effects on human keratinocytes. Fitoterapia,2011,82(8),1265-1271. [View] [PubMed]
  • DiMeo A, Logendran R, et al. (2024). Navigating the Labyrinth of Pregnancy-Related Coverage for Undocumented Immigrants: An Assessment of Current State and Federal Policies.. American journal of public health, 2024, e1-e10. [View] [PubMed]
Pubchem: 5316673
Kegg Ligand: C16911
Chebi: 80790
Nmrshiftdb2: 60021811
Metabolights: MTBLC80790
Pdb Ligand: AFE
CPRiL: 95389
Structure

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

Level: 2

Mol. Weight: 432.38 g/mol

Structure

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

Level: 1

Mol. Weight: 432.38 g/mol

Structure

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

Level: 1

Mol. Weight: 432.38 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 432.38 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 432.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 432.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.75
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.330
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
0.43

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
81.24
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
12.760
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-0.770
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.190
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.250
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
-41.700
Rat (Acute)
2.400
Rat (Chronic Oral)
3.860
Fathead Minnow
3.860
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
586.270
Hydration Free Energy
-7.280
Log(D) at pH=7.4
1.060
Log(P)
1.49
Log S
-4.25
Log(Vapor Pressure)
-11.02
Melting Point
207.86
pKa Acid
5.34
pKa Basic
6.06
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9757
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9757
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9393
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9393
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9320
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9320
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8920
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8920
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8859
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8859
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8767
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8767
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 8 0.8763
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 8 0.8763
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8738
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8738
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.8685
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.8685
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8611
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8611
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8577
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8577
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8508
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8508
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8463
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.8463
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8460
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.8460
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8315
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8315
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8234
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8234
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8220
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.8220
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8157
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.8157
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8144
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8144
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8119
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8119
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8012
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 3 0.8012
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8007
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8007
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7995
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.7995
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7993
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7993
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7949
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7949
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7942
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.7942
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7939
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7939
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7901
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7901
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7887
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7887
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7871
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7871
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7821
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7821
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7818
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7818
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7781
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7781
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7779
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7779
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7757
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7757
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7715
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7715
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7686
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7686
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7622
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7622
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7620
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7620
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7600
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7600
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7497
DNA gyrase subunit A P0AES5 GYRA_SHIFL Shigella flexneri 3 0.7497
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7488
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7488
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7478
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7478
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7474
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7474
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7438
5-methylthioadenosine/S-adenosylhomocysteine deaminase Q7NZ90 Q7NZ90_CHRVO Chromobacterium violaceum 3 0.7438
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7377
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7377
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7371
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7371
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7288
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7288
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7255
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7255
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7248
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7248
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7237
3-phosphoinositide-dependent protein kinase 1 O15530 PDPK1_HUMAN Homo sapiens 3 0.7237
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7227
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7227
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7212
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7212
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
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7209
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7209
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7189
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7189
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7122
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.7122
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7117
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7117
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7115
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.7115
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7104
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 3 0.7104
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7101
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7101
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7070
Succinate dehydrogenase [ubiquinone] iron-sulfur subunit, mitochondrial Q33862 Q33862_ASCSU Ascaris suum 3 0.7070
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7059
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7059
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7055
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7055
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7055
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7055
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7052
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7052
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7052
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7052
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7042
Interstitial collagenase P03956 MMP1_HUMAN Homo sapiens 3 0.7042
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7028
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7028
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7026
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7026
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7022
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7022
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7020
CREB-binding protein Q92793 CBP_HUMAN Homo sapiens 3 0.7020
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7013
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7013
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7007
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7007
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 3 0.7006
Matrix metalloproteinase-20 O60882 MMP20_HUMAN Homo sapiens 3 0.7006

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