Kaempferol, robinoside

Details

• Internal ID: f3f7bf20-8a03-48b9-b6c4-f361475ce557
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3-[3,4,5-trihydroxy-6-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl]oxan-2-yl]oxychromen-4-one
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)C)O)O)O)C6=CC=C(C=C6)O)O)O)O)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)OC5C(C(C(C(O5)C)O)O)O)C6=CC=C(C=C6)O)O)O)O)O)O)O
• InChI: InChI=1S/C33H40O19/c1-10-19(36)23(40)26(43)31(47-10)46-9-17-21(38)25(42)28(45)33(51-17)52-30-22(39)18-15(35)7-14(49-32-27(44)24(41)20(37)11(2)48-32)8-16(18)50-29(30)12-3-5-13(34)6-4-12/h3-8,10-11,17,19-21,23-28,31-38,40-45H,9H2,1-2H3
• InChI Key: PEFASEPMJYRQBW-UHFFFAOYSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₉
• Molecular Weight: 740.70 g/mol
• Exact Mass: 740.21637904 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): -2.89
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 8

Synonyms

• 81992-85-0
• NSC-9222
• Kaempferol, robinoside
• SCHEMBL241940
• DTXSID30871629
• AKOS002137985
• FT-0775595
• 7-[(6-Deoxyhexopyranosyl)oxy]-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-3-yl 6-O-(6-deoxyhexopyranosyl)hexopyranoside
• N-(cyclopropylmethyl)-1-[3-(4-methylphenyl)-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl]piperidine-4-carboxamide

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.4659	46.59%
Caco-2	-	0.9089	90.89%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7552	75.52%
OATP2B1 inhibitior	-	0.5703	57.03%
OATP1B1 inhibitior	+	0.9118	91.18%
OATP1B3 inhibitior	+	0.9107	91.07%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9055	90.55%
P-glycoprotein inhibitior	-	0.4789	47.89%
P-glycoprotein substrate	+	0.5348	53.48%
CYP3A4 substrate	+	0.6197	61.97%
CYP2C9 substrate	-	0.7354	73.54%
CYP2D6 substrate	-	0.8607	86.07%
CYP3A4 inhibition	-	0.8904	89.04%
CYP2C9 inhibition	-	0.9134	91.34%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9500	95.00%
CYP1A2 inhibition	-	0.8713	87.13%
CYP2C8 inhibition	+	0.7912	79.12%
CYP inhibitory promiscuity	-	0.6602	66.02%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.7067	70.67%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.9034	90.34%
Skin irritation	-	0.8277	82.77%
Skin corrosion	-	0.9610	96.10%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7641	76.41%
Micronuclear	+	0.7292	72.92%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.9381	93.81%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.8817	88.17%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	+	0.7770	77.70%
Androgen receptor binding	+	0.6139	61.39%
Thyroid receptor binding	-	0.4931	49.31%
Glucocorticoid receptor binding	+	0.5430	54.30%
Aromatase binding	+	0.5329	53.29%
PPAR gamma	+	0.7201	72.01%
Honey bee toxicity	-	0.7809	78.09%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5450	54.50%
Fish aquatic toxicity	+	0.9179	91.79%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.27%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.29%	91.49%
CHEMBL2581	P07339	Cathepsin D	97.69%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.86%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.16%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.39%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	94.15%	94.73%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	93.89%	95.64%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.13%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.44%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.15%	85.14%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	86.36%	95.78%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.32%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.76%	97.09%
CHEMBL242	Q92731	Estrogen receptor beta	84.57%	98.35%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.42%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.21%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.25%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.17%	86.92%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.94%	94.80%
CHEMBL4208	P20618	Proteasome component C5	80.41%	90.00%
CHEMBL3194	P02766	Transthyretin	80.08%	90.71%

Plants that contains it

• Aconitum anthora
• Allium myrianthum
• Androsace umbellata
• Astragalus cicer
• Astragalus dipelta
• Astragalus eupeplus
• Astragalus falcatus
• Astragalus laxmannii
• Astragalus levieri
• Cephalocereus senilis
• Crotalaria trichotoma
• Gliricidia sepium
• Lepidium cartilagineum
• Luculia pinceana
• Melilotus officinalis
• Oxytropis muricata
• Phaseolus vulgaris
• Pueraria montana var. lobata
• Vinca major

Cross-Links

• PubChem: 5351997
• NPASS: NPC112220
• LOTUS: LTS0227269
• wikiData: Q82227855