Kaempferol 3-O-rhamnoside - Compound Card

Kaempferol 3-O-rhamnoside

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Kaempferol 3-O-rhamnoside

Structure
Zoomed Structure
  • Family: Plantae - Umbelliferae
  • 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/t8-,15-,17+,18+,21-/m0/s1
InChIKey SOSLMHZOJATCCP-AEIZVZFYSA-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 Epilobium hirsutum Onagraceae Plantae 210355
2 Moringa oleifera Moringaceae Plantae 3735
3 Elaeophorbia drupifera Euphorbiaceae Plantae 212879
4 Pentadesma butyracea Guttiferae Plantae 198785
5 Ferula longipes Umbelliferae Plantae 1514033

Showing of synonyms

  • Tala M, Wabo H, et al. (2013). A prenylated xanthone and antiproliferative compounds from leaves of Pentadesma butyracea. Phytochemistry Letters, 2013, 6(3), 326-330. [View]
  • Voukeng IK, Nganou BK, et al. (2017). Antibacterial activities of the methanol extract, fractions and compounds from Elaeophorbia drupifera (Thonn.) Stapf. (Euphorbiaceae).. BMC complementary and alternative medicine,2017, 17(1), 28. [View] [PubMed]
  • Bouratoua A, Khalfallah A, et al. (2018). Chemical composition and antioxidant activity of aerial parts of Ferula longipes Coss. ex Bonnier and Maury. Nat Prod Res,2018,32(16),1873-1880. [View] [PubMed]
  • Manguro LO, Lemmen P. (2007). Phenolics of Moringa oleifera leaves.. Natural Product Research,2007,21(1),56-68. [View] [PubMed]
  • Barakat HH, Hussein SAM, et al. (1997). Polyphenolic metabolites of Epilobium hirsutum. Phytochemistry,1997,46(5),935-941. [View]
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

Antibacterial
Antioxidant

Absorption

Caco-2 (logPapp)
-6.78
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
0.42

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.970
Plasma Protein Binding
86.49
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
-0.920
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
5.260
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
-42.110
Rat (Acute)
2.400
Rat (Chronic Oral)
3.860
Fathead Minnow
3.840
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
588.270
Hydration Free Energy
-7.280
Log(D) at pH=7.4
1.030
Log(P)
1.76
Log S
-4.29
Log(Vapor Pressure)
-11.15
Melting Point
209.94
pKa Acid
5.35
pKa Basic
6.07
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9773
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9773
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9300
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9300
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9283
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.9283
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9042
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9042
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8897
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8897
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8825
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.8825
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8771
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8771
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8761
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 4 0.8761
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8469
Aldos-2-ulose dehydratase P84193 AUD_PHACH Phanerodontia chrysosporium 3 0.8469
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8379
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 4 0.8379
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8346
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8346
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8325
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8325
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.8240
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 7 0.8240
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8229
Gag-Pol polyprotein P05896 POL_SIVM1 Simian immunodeficiency virus 4 0.8229
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8220
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.8220
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8202
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8202
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8190
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8190
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8153
Tyrosine-protein kinase JAK3 P52333 JAK3_HUMAN Homo sapiens 3 0.8153
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8136
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8136
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8029
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8029
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8005
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8005
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7954
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7954
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7928
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 4 0.7928
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7876
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7876
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7825
Transcriptional regulator, PadR-like family A2RI36 A2RI36_LACLM Lactococcus lactis subsp. cremoris 3 0.7825
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7823
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7823
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7778
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7778
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7766
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7766
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7760
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7760
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7759
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.7759
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7747
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7747
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7715
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7715
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7682
Botulinum neurotoxin type A P0DPI0 BXA1_CLOBO Clostridium botulinum 3 0.7682
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7652
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7652
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7587
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.7587
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7556
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7556
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7553
Avidin P02701 AVID_CHICK Gallus gallus 3 0.7553
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7550
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7550
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7519
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7519
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7455
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7455
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7442
GCN5-related N-acetyltransferase B1YEL6 B1YEL6_EXIS2 Exiguobacterium sibiricum 3 0.7442
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7434
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7434
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7418
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7418
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7393
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7393
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7379
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7379
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7351
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7351
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7292
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7292
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7256
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7256
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 3 0.7256
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7256
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7237
Prothrombin P00734 THRB_HUMAN Homo sapiens 3 0.7237
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7230
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7230
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7147
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7147
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7097
Beta-lactamase Q9L5C8 Q9L5C8_ECOLX Escherichia coli 3 0.7097
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7094
Serine/threonine-protein kinase PLK1 P53350 PLK1_HUMAN Homo sapiens 3 0.7094
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7074
Endoplasmin P41148 ENPL_CANLF Canis lupus familiaris 5 0.7074
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7052
Flavin reductase (NADPH) P30043 BLVRB_HUMAN Homo sapiens 3 0.7052
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7038
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7038
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7025
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7025
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7003
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.7003
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7002
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7002

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