kaempferol 3-O-beta-L-glucopyranoside

Details

• Internal ID: ea5ee268-6ee1-4854-b151-16615531553e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides
• IUPAC Name: 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O
• SMILES (Isomeric): C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@@H]4[C@H]([C@@H]([C@H]([C@@H](O4)CO)O)O)O)O
• InChI: InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m0/s1
• InChI Key: JPUKWEQWGBDDQB-LQSBFMDOSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₀O₁₁
• Molecular Weight: 448.40 g/mol
• Exact Mass: 448.10056145 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): -0.24
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 4

Synonyms

• CHEBI:75791
• Astragarin
• MLS002473047
• CHEMBL1572115
• HMS2223B14
• SMR001397151
• Q27145543
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-3-yl beta-L-glucopyranoside
• 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5116	51.16%
Caco-2	-	0.9102	91.02%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6068	60.68%
OATP2B1 inhibitior	+	0.5869	58.69%
OATP1B1 inhibitior	+	0.8875	88.75%
OATP1B3 inhibitior	+	0.9265	92.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.5444	54.44%
P-glycoprotein inhibitior	-	0.6120	61.20%
P-glycoprotein substrate	-	0.7828	78.28%
CYP3A4 substrate	+	0.6012	60.12%
CYP2C9 substrate	-	0.6762	67.62%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.9193	91.93%
CYP2C9 inhibition	-	0.9296	92.96%
CYP2C19 inhibition	-	0.9289	92.89%
CYP2D6 inhibition	-	0.9513	95.13%
CYP1A2 inhibition	-	0.9084	90.84%
CYP2C8 inhibition	+	0.8532	85.32%
CYP inhibitory promiscuity	-	0.7728	77.28%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7144	71.44%
Eye corrosion	-	0.9930	99.30%
Eye irritation	-	0.7324	73.24%
Skin irritation	-	0.8036	80.36%
Skin corrosion	-	0.9691	96.91%
Ames mutagenesis	+	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5892	58.92%
Micronuclear	+	0.6533	65.33%
Hepatotoxicity	-	0.6071	60.71%
skin sensitisation	-	0.9122	91.22%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7272	72.72%
Acute Oral Toxicity (c)	III	0.4045	40.45%
Estrogen receptor binding	+	0.7820	78.20%
Androgen receptor binding	+	0.7749	77.49%
Thyroid receptor binding	-	0.5057	50.57%
Glucocorticoid receptor binding	+	0.7121	71.21%
Aromatase binding	+	0.6263	62.63%
PPAR gamma	+	0.7114	71.14%
Honey bee toxicity	-	0.7722	77.22%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6350	63.50%
Fish aquatic toxicity	+	0.8218	82.18%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL220	P22303	Acetylcholinesterase	12 nM	IC50	via Super-PRED
CHEMBL205	P00918	Carbonic anhydrase II	168 nM	Ki	via Super-PRED
CHEMBL2326	P43166	Carbonic anhydrase VII	423.7 nM	Ki	via Super-PRED
CHEMBL3242	O43570	Carbonic anhydrase XII	4.9 nM	Ki	via Super-PRED
CHEMBL5422	P07237	Protein disulfide-isomerase	15.5 nM	AC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.21%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.19%	89.00%
CHEMBL2581	P07339	Cathepsin D	95.98%	98.95%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	95.81%	95.64%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.62%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	89.84%	94.73%
CHEMBL3194	P02766	Transthyretin	89.10%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.84%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.33%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.75%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.13%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.56%	94.45%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	85.93%	95.78%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	84.78%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.46%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	81.71%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	81.06%	98.35%

Plants that contains it

• Aconitum violaceum
• Actiniopteris radiata
• Agave americana
• Aglaia laxiflora
• Agrimonia eupatoria
• Alcea nudiflora
• Artemisia carvifolia
• Artemisia lactiflora
• Astragalus galegiformis
• Atraphaxis frutescens
• Attalea phalerata
• Berlandiera pumila
• Callicarpa maingayi
• Campanula hypopolia
• Catalpa ovata
• Centaurea corcubionensis
• Cephalaria uralensis
• Citrus medica
• Codonopsis pilosula
• Crepidiastrum sonchifolium
• Crotalaria aegyptiaca
• Delphinium shawurense
• Dendrophthoe falcata
• Dicoma capensis
• Digitalis isabelliana
• Dipsacus inermis
• Dorstenia barteri
• Duguetia calycina
• Ericameria parryi
• Euphorbia turczaninowii
• Fagraea gracilipes
• Garcinia pyrifera
• Garcinia xipshuanbannaensis
• Geranium sylvaticum
• Greenwayodendron oliveri
• Gutierrezia microcephala
• Haplophyllum ferganicum
• Helichrysum graveolens
• Iryanthera paraensis
• Jacaranda mimosifolia
• Krameria lappacea
• Lathyrus nissolia
• Leonurus persicus
• Magnolia sieboldii
• Ophryosporus floribundus
• Payena lucida
• Peltogyne floribunda
• Phalaris canariensis
• Philotheca spicata
• Plumbagella micrantha
• Pteridium aquilinum
• Quassia indica
• Ratibida mexicana
• Ribes nigrum
• Rivina humilis
• Salvia cyanescens
• Scopolia carniolica
• Sonchus ortunoi
• Sorbaria sorbifolia
• Styrax ferrugineus
• Vincetoxicum hirundinaria

Cross-Links

• PubChem: 9911508
• NPASS: NPC77672
• ChEMBL: CHEMBL1572115
• LOTUS: LTS0052093
• wikiData: Q27145543