5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxychroman-4-one

Details

• Internal ID: b0e66b18-d1e0-44fd-b3f8-d81362c417a3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O
• SMILES (Isomeric): COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=C(C=C3)O)O
• InChI: InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3
• InChI Key: DJOJDHGQRNZXQQ-UHFFFAOYSA-N
• Popularity: 287 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

• 520-29-6
• 2957-21-3
• (RS)-Sakuranetin
• NSC-407228
• 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydrochromen-4-one
• CHEMBL74852
• NSC407228
• 5-Hydroxy-2-(4-hydroxy-phenyl)-7-methoxy-chroman-4-one
• 5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
• 4H-1-Benzopyran-4-one, 2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-
• Sakauranetin
• Dihydrogenkwanin
• MLS000876793
• SCHEMBL555541
• MEGxp0_000557
• ACon1_000001
• DTXSID10874774
• 2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
• DJOJDHGQRNZXQQ-UHFFFAOYSA-N
• HMS2271F13
• 4/',5-Dihydroxy-7-methoxyflavanone
• BDBM50049387
• MFCD07782262
• AKOS015965397
• 5,4''-Dihydroxy-7-o-methoxyflavanone
• NCGC00168885-01
• AC-20247
• AC-34929
• SMR000440561
• XD161714
• FT-0650767
• Flavanone,5-dihydroxy-7-methoxy-, (S)-(-)-
• A871097
• L000892
• BRD-A32263173-001-01-2
• 5-Hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-chromen-4-one #
• 4H-1-Benzopyran-4-one,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9764	97.64%
Caco-2	+	0.6627	66.27%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8644	86.44%
OATP2B1 inhibitior	-	0.6139	61.39%
OATP1B1 inhibitior	+	0.9323	93.23%
OATP1B3 inhibitior	+	0.9949	99.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6124	61.24%
P-glycoprotein inhibitior	-	0.7570	75.70%
P-glycoprotein substrate	-	0.9388	93.88%
CYP3A4 substrate	+	0.5232	52.32%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	+	0.5657	56.57%
CYP2C9 inhibition	+	0.9550	95.50%
CYP2C19 inhibition	+	0.9600	96.00%
CYP2D6 inhibition	+	0.5000	50.00%
CYP1A2 inhibition	+	0.9497	94.97%
CYP2C8 inhibition	-	0.6851	68.51%
CYP inhibitory promiscuity	+	0.7541	75.41%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.5163	51.63%
Eye corrosion	-	0.9828	98.28%
Eye irritation	+	0.8679	86.79%
Skin irritation	-	0.6806	68.06%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	+	0.5246	52.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.7529	75.29%
Micronuclear	+	0.8059	80.59%
Hepatotoxicity	-	0.7310	73.10%
skin sensitisation	-	0.9606	96.06%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6189	61.89%
Acute Oral Toxicity (c)	III	0.5646	56.46%
Estrogen receptor binding	+	0.6806	68.06%
Androgen receptor binding	+	0.7614	76.14%
Thyroid receptor binding	+	0.6318	63.18%
Glucocorticoid receptor binding	+	0.7398	73.98%
Aromatase binding	+	0.6147	61.47%
PPAR gamma	+	0.7609	76.09%
Honey bee toxicity	-	0.8565	85.65%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7166	71.66%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	3400 nM; 3400 nM	Ki; Ki	PMID: 8691424; PMID: 8576921
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	5623.4 nM	Potency	via CMAUP
CHEMBL3797	Q13315	Serine-protein kinase ATM	39810.7 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.64%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.72%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.71%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.39%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.23%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.52%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.25%	99.15%
CHEMBL4208	P20618	Proteasome component C5	90.10%	90.00%
CHEMBL2581	P07339	Cathepsin D	89.74%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.29%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.63%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.60%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.02%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.35%	86.33%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	81.86%	85.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.51%	99.17%
CHEMBL2535	P11166	Glucose transporter	81.25%	98.75%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.20%	93.99%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	80.98%	92.68%

Plants that contains it

• Ageratina tristis
• Artemisia campestris
• Artemisia monosperma
• Artemisia xanthochroa
• Baccharis intermixta
• Baccharis salicifolia subsp. salicifolia
• Betula pubescens
• Blumea fistulosa
• Boesenbergia rotunda
• Bonnetia paniculata
• Brickellia vernicosa
• Chromolaena odorata
• Chromolaena tunariensis
• Corymbia maculata
• Cryptocarya obovata
• Dittrichia graveolens
• Dittrichia viscosa subsp. viscosa
• Dodonaea viscosa
• Heliotropium glutinosum
• Isodon oresbius
• Larrea tridentata
• Lippia origanoides
• Microtropis japonica
• Mimosa zimapanensis
• Neolitsea daibuensis
• Ophryosporus macrodon
• Oxytropis falcata
• Piper crassinervium
• Piper lhotzkyanum
• Piper marginatum
• Piper permucronatum
• Plazia daphnoides
• Poecilanthe parviflora
• Populus tremuloides
• Prunus avium
• Prunus maximowiczii
• Prunus pseudocerasus
• Pyracantha coccinea
• Xanthorrhoea resinosa

Cross-Links

• PubChem: 348130
• NPASS: NPC329203
• ChEMBL: CHEMBL74852
• LOTUS: LTS0175293
• wikiData: Q104982551