Kushenol C

Details

• Internal ID: a3cffefd-f861-4783-85af-1376ffad91dc
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavones > 8-prenylated flavones
• IUPAC Name: 2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]chromen-4-one
• SMILES (Canonical): CC(=CCC(CC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=C(C=C(C=C3)O)O)O)C(=C)C)C
• SMILES (Isomeric): CC(=CC[C@H](CC1=C2C(=C(C=C1O)O)C(=O)C(=C(O2)C3=C(C=C(C=C3)O)O)O)C(=C)C)C
• InChI: InChI=1S/C25H26O7/c1-12(2)5-6-14(13(3)4)9-17-19(28)11-20(29)21-22(30)23(31)25(32-24(17)21)16-8-7-15(26)10-18(16)27/h5,7-8,10-11,14,26-29,31H,3,6,9H2,1-2,4H3/t14-/m1/s1
• InChI Key: WAAPHYJTKSTXSX-CQSZACIVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₇
• Molecular Weight: 438.50 g/mol
• Exact Mass: 438.16785316 g/mol
• Topological Polar Surface Area (TPSA): 127.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.08
• H-Bond Acceptor: 7
• H-Bond Donor: 5
• Rotatable Bonds: 6

Synonyms

• 99119-73-0
• 2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2R)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]chromen-4-one
• 4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2R)-5-methyl-2-(1-methylethenyl)-4-hexen-1-yl]-
• 4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-5-methoxy-8-((2R)-5-methyl-2-(1-methylethenyl)-4-hexenyl)-, (2R,3R)-
• 4H-1-Benzopyran-4-one, 2-(2,4-dihydroxyphenyl)-2,3-dihydro-3,7-dihydroxy-5-methoxy-8-[(2R)-5-methyl-2-(1-methylethenyl)-4-hexenyl]-, (2R,3R)-
• SCHEMBL564580
• ZDA11969
• LMPK12112514
• AKOS040761959
• HY-108966
• CS-0033818
• (2S,3S)-2-(2,4-dihydroxyphenyl)-3,7-dihydroxy-5-methoxy-8-[(2S)-5-methyl-2-prop-1-en-2-ylhex-4-enyl]-2,3-dihydrochromen-4-one
• (R)-2-(2,4-Dihydroxyphenyl)-3,5,7-trihydroxy-8-(5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl)-4H-chromen-4-one
• 2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-[(2R)-2-isopropenyl-5-methyl-hex-4-enyl]chromen-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9850	98.50%
Caco-2	-	0.7800	78.00%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5788	57.88%
OATP2B1 inhibitior	+	0.5767	57.67%
OATP1B1 inhibitior	-	0.3352	33.52%
OATP1B3 inhibitior	+	0.9030	90.30%
MATE1 inhibitior	-	0.7200	72.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9067	90.67%
P-glycoprotein inhibitior	+	0.6063	60.63%
P-glycoprotein substrate	+	0.5562	55.62%
CYP3A4 substrate	+	0.5894	58.94%
CYP2C9 substrate	+	0.6262	62.62%
CYP2D6 substrate	-	0.8300	83.00%
CYP3A4 inhibition	-	0.6189	61.89%
CYP2C9 inhibition	+	0.8852	88.52%
CYP2C19 inhibition	+	0.8737	87.37%
CYP2D6 inhibition	-	0.7383	73.83%
CYP1A2 inhibition	+	0.7902	79.02%
CYP2C8 inhibition	+	0.5847	58.47%
CYP inhibitory promiscuity	+	0.8931	89.31%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7219	72.19%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.6922	69.22%
Skin irritation	-	0.7185	71.85%
Skin corrosion	-	0.9115	91.15%
Ames mutagenesis	+	0.5163	51.63%
Human Ether-a-go-go-Related Gene inhibition	+	0.7439	74.39%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6302	63.02%
skin sensitisation	-	0.7140	71.40%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6679	66.79%
Acute Oral Toxicity (c)	III	0.6383	63.83%
Estrogen receptor binding	+	0.9034	90.34%
Androgen receptor binding	+	0.7316	73.16%
Thyroid receptor binding	+	0.7164	71.64%
Glucocorticoid receptor binding	+	0.8455	84.55%
Aromatase binding	+	0.6942	69.42%
PPAR gamma	+	0.8736	87.36%
Honey bee toxicity	-	0.7963	79.63%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9963	99.63%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.46%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.34%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.01%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.02%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	92.92%	94.73%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.63%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.06%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.24%	86.33%
CHEMBL3194	P02766	Transthyretin	85.85%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.59%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.75%	90.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.95%	94.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	82.12%	99.15%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.80%	95.64%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.31%	93.10%
CHEMBL1929	P47989	Xanthine dehydrogenase	80.25%	96.12%

Plants that contains it

• 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
• Gentiana macrophylla
• Gymnocalycium schickendantzii
• Haplophyllum obtusifolium
• Helichrysum tenuifolium
• Hypericum styphelioides
• Linnaea chinensis
• Lythrum salicaria
• Monsonia senegalensis
• Myrica rubra
• Onopordum acanthium
• Pancratium sickenbergeri
• Pinalia anomala
• Piper regnellii
• Plathymenia reticulata
• Pteridium esculentum
• Simarouba glauca
• Sophora flavescens
• Stenocereus laevigatus
• Syzygium polycephaloides
• Varronia leucocephala
• Vellozia nanuzae
• Vernonanthura fagifolia

Cross-Links

• PubChem: 5481237
• NPASS: NPC299027
• LOTUS: LTS0136574
• wikiData: Q83128175