5-Hydroxy-7-methoxyflavanone

Details

• Internal ID: ea10fd52-7da5-4890-a87b-4bbb343239d3
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: 5-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=CC=C3)O
• SMILES (Isomeric): COC1=CC(=C2C(=O)CC(OC2=C1)C3=CC=CC=C3)O
• InChI: InChI=1S/C16H14O4/c1-19-11-7-12(17)16-13(18)9-14(20-15(16)8-11)10-5-3-2-4-6-10/h2-8,14,17H,9H2,1H3
• InChI Key: ORJDDOBAOGKRJV-UHFFFAOYSA-N
• Popularity: 123 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28 g/mol
• Exact Mass: 270.08920892 g/mol
• Topological Polar Surface Area (TPSA): 55.80 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 3.11
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• 5-Hydroxy-7-methoxyflavanone
• 75291-74-6
• 480-37-5
• 5-hydroxy-7-methoxy-2-phenylchroman-4-one
• 5-hydroxy-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• Pinocembrin-7-methylether
• (+/-)-Pinostrobin
• (S)-2,3-Dihydro-5-hydroxy-7-methoxy-2-phenyl-4-benzopyrone
• EINECS 207-548-1
• ()-Pinostrobin
• ( inverted exclamation markA)-Pinostrobin
• Chloroformic acidN-amyl ester
• CHEMBL210800
• SCHEMBL1485747
• (2R)-5-hydroxy-7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one
• ORJDDOBAOGKRJV-UHFFFAOYSA-N
• BCP09997
• LMPK12140216
• MFCD00017481
• AKOS016009493
• (+/-)-Pinostrobin, >=99.0% (TLC)
• FT-0620476
• FT-0632188

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9862	98.62%
Caco-2	+	0.7064	70.64%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8182	81.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9476	94.76%
OATP1B3 inhibitior	+	0.9968	99.68%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.5752	57.52%
P-glycoprotein inhibitior	-	0.6914	69.14%
P-glycoprotein substrate	-	0.9615	96.15%
CYP3A4 substrate	-	0.5096	50.96%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7429	74.29%
CYP3A4 inhibition	+	0.6242	62.42%
CYP2C9 inhibition	+	0.9238	92.38%
CYP2C19 inhibition	+	0.9533	95.33%
CYP2D6 inhibition	-	0.7102	71.02%
CYP1A2 inhibition	+	0.9408	94.08%
CYP2C8 inhibition	+	0.4500	45.00%
CYP inhibitory promiscuity	+	0.6591	65.91%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9313	93.13%
Carcinogenicity (trinary)	Non-required	0.4991	49.91%
Eye corrosion	-	0.9778	97.78%
Eye irritation	+	0.6878	68.78%
Skin irritation	-	0.6523	65.23%
Skin corrosion	-	0.9760	97.60%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5462	54.62%
Micronuclear	+	0.7759	77.59%
Hepatotoxicity	-	0.6560	65.60%
skin sensitisation	-	0.9585	95.85%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	+	0.6228	62.28%
Acute Oral Toxicity (c)	III	0.5097	50.97%
Estrogen receptor binding	+	0.6610	66.10%
Androgen receptor binding	+	0.6448	64.48%
Thyroid receptor binding	-	0.5130	51.30%
Glucocorticoid receptor binding	+	0.5685	56.85%
Aromatase binding	+	0.7127	71.27%
PPAR gamma	+	0.7062	70.62%
Honey bee toxicity	-	0.8832	88.32%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.7021	70.21%

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	98.92%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.46%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.02%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.07%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.85%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.74%	99.15%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	92.48%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.18%	86.33%
CHEMBL4208	P20618	Proteasome component C5	86.92%	90.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.32%	97.09%
CHEMBL2535	P11166	Glucose transporter	82.03%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.88%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.77%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.75%	89.00%

Plants that contains it

• Alnus firma
• Boesenbergia rotunda
• Cajanus cajan
• Cryptocarya chinensis
• Drosera gigantea
• Haplopappus remyanus
• Isodon oresbius
• Kaempferia parviflora
• Laennecia filaginoides
• Laggera crispata
• Leptospermum scoparium
• Lindera umbellata
• Miliusa balansae
• Miliusa sinensis
• Muntingia calabura
• Onychium siliculosum
• Oxytropis falcata
• Persicaria ferruginea
• Persicaria senegalensis
• Pinalia pandurata
• Pinus lambertiana
• Pinus morrisonicola
• Pinus sibirica
• Piper hispidum
• Piper methysticum
• Piper porphyrophyllum
• Populus balsamifera
• Populus laurifolia
• Renealmia nicolaioides
• Salvia texana
• Sarcandra glabra
• Sarcandra glabra subsp. brachystachys
• Taxandria spathulata
• Uvaria chamae
• Uvaria rufa
• Zingiber officinale
• Zuccagnia punctata

Cross-Links

• PubChem: 4101463
• NPASS: NPC235117
• LOTUS: LTS0033236
• wikiData: Q105149215