Isosakuranetin

Details

• Internal ID: 57cdb242-d6bd-42a2-a1b0-65a69af3964f
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 4-O-methylated flavonoids
• IUPAC Name: (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC=C(C=C1)C2CC(=O)C3=C(C=C(C=C3O2)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)[C@@H]2CC(=O)C3=C(C=C(C=C3O2)O)O
• InChI: InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
• InChI Key: HMUJXQRRKBLVOO-AWEZNQCLSA-N
• Popularity: 57 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.81
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

• 480-43-3
• 4'-Methylnaringenin
• Isosakutanetin
• naringenin 4'-methyl ether
• (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydrochromen-4-one
• UNII-U02X7TF8UA
• U02X7TF8UA
• CHEMBL470266
• CHEBI:27552
• (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4-benzopyrone
• EINECS 207-551-8
• Citrifoliol
• (S)-5,7-dihydroxy-2-(4-methoxyphenyl)chroman-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (2S)-
• 4'-methoxy-5,7-dihydroxyflavanone
• D01FJE
• naringenin 4''-methyl ether
• SCHEMBL676015
• MEGxp0_001686
• ACon1_000171
• GTPL10299
• DTXSID60963980
• HMUJXQRRKBLVOO-AWEZNQCLSA-N
• (2S)-naringenin 4'-methyl ether
• GLXC-14373
• 4'-Methoxy-5,7-dihydroxyflavonone
• HY-N2131
• 5,7-dihydroxy-4''-methoxyflavanone
• BDBM50325673
• LMPK12140355
• s9438
• (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one
• AKOS032948348
• CCG-208396
• NCGC00163576-01
• NCGC00163576-02
• AC-34925
• MS-24084
• (2S)-5,7-Dihydroxy-4'-methoxyflavanone
• CS-0018682
• A17101
• C05334
• A871979
• SR-05000002273
• Q3459109
• SR-05000002273-2
• BRD-K19341706-001-01-7
• (S)-2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• (2S)-2,3-Dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one
• (2S)-5,7-dihydroxy-2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-methoxyphenyl)-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9479	94.79%
Caco-2	+	0.7139	71.39%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7898	78.98%
OATP2B1 inhibitior	-	0.7404	74.04%
OATP1B1 inhibitior	+	0.9519	95.19%
OATP1B3 inhibitior	+	0.9873	98.73%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.7369	73.69%
P-glycoprotein inhibitior	-	0.8275	82.75%
P-glycoprotein substrate	-	0.9499	94.99%
CYP3A4 substrate	+	0.5505	55.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	+	0.8936	89.36%
CYP2C9 inhibition	+	0.9261	92.61%
CYP2C19 inhibition	+	0.9558	95.58%
CYP2D6 inhibition	+	0.6630	66.30%
CYP1A2 inhibition	+	0.9526	95.26%
CYP2C8 inhibition	-	0.6944	69.44%
CYP inhibitory promiscuity	+	0.8343	83.43%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5741	57.41%
Eye corrosion	-	0.9835	98.35%
Eye irritation	+	0.8997	89.97%
Skin irritation	-	0.6810	68.10%
Skin corrosion	-	0.9428	94.28%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6390	63.90%
Micronuclear	+	0.7859	78.59%
Hepatotoxicity	-	0.7343	73.43%
skin sensitisation	-	0.9455	94.55%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6124	61.24%
Acute Oral Toxicity (c)	III	0.6169	61.69%
Estrogen receptor binding	+	0.7676	76.76%
Androgen receptor binding	+	0.7604	76.04%
Thyroid receptor binding	+	0.7385	73.85%
Glucocorticoid receptor binding	+	0.7815	78.15%
Aromatase binding	+	0.6656	66.56%
PPAR gamma	+	0.8023	80.23%
Honey bee toxicity	-	0.8693	86.93%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.6671	66.71%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2231	P04798	Cytochrome P450 1A1	2196 nM	IC50	PMID: 20696580
CHEMBL3356	P05177	Cytochrome P450 1A2	3147 nM	IC50	PMID: 20696580
CHEMBL4878	Q16678	Cytochrome P450 1B1	1024 nM	IC50	PMID: 20696580

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.08%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.76%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.08%	96.09%
CHEMBL4208	P20618	Proteasome component C5	94.33%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.96%	97.09%
CHEMBL1929	P47989	Xanthine dehydrogenase	92.97%	96.12%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.40%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.46%	94.45%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	89.77%	99.23%
CHEMBL2581	P07339	Cathepsin D	89.24%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.17%	94.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	86.12%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.26%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.05%	85.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.87%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.79%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.69%	86.33%
CHEMBL2535	P11166	Glucose transporter	82.48%	98.75%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.34%	93.40%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.03%	92.62%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	80.03%	85.11%

Plants that contains it

• Ageratina altissima
• Artemisia campestris
• Artemisia xanthochroa
• Baccharis dracunculifolia
• Baccharis vaccinoides
• Calceolaria hypericina
• Chromolaena odorata
• Citrus × aurantium
• Citrus deliciosa
• Clinopodium laxiflorum
• Clinopodium umbrosum
• Commiphora socotrana
• Cyclotrichium niveum
• Diplostephium cinereum
• Dolichlasium lagascae
• Eriodictyon californicum
• Eriodictyon californicum
• Gymnosperma glutinosum
• Heteroplexis microcephala
• Hypenia salzmannii
• Lycium bridgesii
• Piper crassinervium
• Piper marginatum
• Plazia daphnoides
• Populus cathayana
• Populus grandidentata
• Populus laurifolia
• Populus suaveolens
• Populus tremuloides
• Proustia cuneifolia
• Prunus domestica
• Prunus leveilleana
• Vitex quinata
• Wyethia glabra
• Wyethia helenioides

Cross-Links

• PubChem: 160481
• NPASS: NPC274784
• ChEMBL: CHEMBL470266
• LOTUS: LTS0268841
• wikiData: Q3459109