Luteone

Details

• Internal ID: b2a0eccb-3818-4e35-9fc7-6f60e4e38a3b
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 6-prenylated isoflavanones
• IUPAC Name: 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• SMILES (Canonical): CC(=CCC1=C(C2=C(C=C1O)OC=C(C2=O)C3=C(C=C(C=C3)O)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C2=C(C=C1O)OC=C(C2=O)C3=C(C=C(C=C3)O)O)O)C
• InChI: InChI=1S/C20H18O6/c1-10(2)3-5-13-16(23)8-17-18(19(13)24)20(25)14(9-26-17)12-6-4-11(21)7-15(12)22/h3-4,6-9,21-24H,5H2,1-2H3
• InChI Key: MMPVAPMCVABQPS-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₈O₆
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.11033829 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.79
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 41743-56-0
• Luteone (isoflavone)
• UNII-FU3E0232IF
• FU3E0232IF
• CHEBI:27917
• 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)chromen-4-one
• DTXSID00194574
• 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-
• 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4H-chromen-4-one
• 6-isopentenyl-2'-hydroxygenistein
• Luteone?
• CHEMBL549617
• MEGxp0_000744
• SCHEMBL1667408
• ACon1_000606
• DTXCID40117065
• GLXC-17705
• HY-N3353
• LMPK12050287
• AKOS032948669
• NCGC00168918-01
• CS-0023971
• FT-0639733
• A825642
• Q6705431
• BRD-K34029608-001-01-8
• B0005-117275
• 3-(2,4-Dihydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 9CI
• 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-1-benzopyran-4-one
• 3-(2,4-dihydroxyphenyl)-5,7-dihydroxy-6-(3-methylbut-2-enyl)-4H-chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9914	99.14%
Caco-2	+	0.5868	58.68%
Blood Brain Barrier	-	0.5379	53.79%
Human oral bioavailability	+	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	+	0.5829	58.29%
OATP1B1 inhibitior	+	0.8987	89.87%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5847	58.47%
P-glycoprotein inhibitior	-	0.6797	67.97%
P-glycoprotein substrate	-	0.7444	74.44%
CYP3A4 substrate	+	0.5501	55.01%
CYP2C9 substrate	-	0.5755	57.55%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	+	0.5630	56.30%
CYP2C9 inhibition	+	0.9394	93.94%
CYP2C19 inhibition	+	0.9320	93.20%
CYP2D6 inhibition	-	0.7264	72.64%
CYP1A2 inhibition	+	0.9115	91.15%
CYP2C8 inhibition	+	0.5157	51.57%
CYP inhibitory promiscuity	+	0.9498	94.98%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7012	70.12%
Eye corrosion	-	0.9902	99.02%
Eye irritation	+	0.6964	69.64%
Skin irritation	-	0.7159	71.59%
Skin corrosion	-	0.9161	91.61%
Ames mutagenesis	+	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6350	63.50%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7133	71.33%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.6642	66.42%
Acute Oral Toxicity (c)	III	0.6307	63.07%
Estrogen receptor binding	+	0.9262	92.62%
Androgen receptor binding	+	0.8550	85.50%
Thyroid receptor binding	+	0.5857	58.57%
Glucocorticoid receptor binding	+	0.8458	84.58%
Aromatase binding	+	0.7112	71.12%
PPAR gamma	+	0.9189	91.89%
Honey bee toxicity	-	0.8554	85.54%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9944	99.44%

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	99.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.74%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.07%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.49%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.49%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	91.28%	94.73%
CHEMBL4208	P20618	Proteasome component C5	86.57%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.08%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.58%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	81.38%	91.49%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.74%	94.00%
CHEMBL3194	P02766	Transthyretin	80.48%	90.71%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.39%	95.64%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.03%	96.12%

Plants that contains it

• Amaranthus spinosus
• Asimina parviflora
• Atraphaxis spinosa
• Baccharis neglecta
• Centaurea cuneifolia subsp. cuneifolia
• Chondrodendron tomentosum
• Clerodendrum bungei
• Diospyros ebenum
• Embelia parviflora
• Embelia schimperi
• Ephedra sinica
• Epilobium hirsutum
• Erysimum leptophyllum
• Erythrina melanacantha
• Esenbeckia leiocarpa
• Euphorbia jolkinii
• Faramea multiflora
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Laburnum anagyroidis
• Linnaea chinensis
• Lupinus albus
• Lupinus elegans
• Lupinus luteus
• Lupinus pubescens
• Lupinus subcarnosus
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Phaseolus lunatus
• Pinalia anomala
• Piper dilatatum
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 5281797
• NPASS: NPC268204
• ChEMBL: CHEMBL549617
• LOTUS: LTS0113884
• wikiData: Q6705431