(2r,3r)-(-)-3,5-Dihydroxy-6,7-dimethoxyflavanone

Details

• Internal ID: c5abb28a-de4c-4525-8605-766bcff5d72a
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: (2R,3R)-3,5-dihydroxy-6,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C(=C2C(=C1)OC(C(C2=O)O)C3=CC=CC=C3)O)OC
• SMILES (Isomeric): COC1=C(C(=C2C(=C1)O[C@@H]([C@H](C2=O)O)C3=CC=CC=C3)O)OC
• InChI: InChI=1S/C17H16O6/c1-21-11-8-10-12(14(19)17(11)22-2)13(18)15(20)16(23-10)9-6-4-3-5-7-9/h3-8,15-16,19-20H,1-2H3/t15-,16+/m0/s1
• InChI Key: AIGSRZAEUVTPPQ-JKSUJKDBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₁₆O₆
• Molecular Weight: 316.30 g/mol
• Exact Mass: 316.09468823 g/mol
• Topological Polar Surface Area (TPSA): 85.20 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.09
• H-Bond Acceptor: 6
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9730	97.30%
Caco-2	+	0.5110	51.10%
Blood Brain Barrier	-	0.8000	80.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8156	81.56%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8884	88.84%
OATP1B3 inhibitior	+	0.9738	97.38%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.7194	71.94%
P-glycoprotein inhibitior	-	0.4423	44.23%
P-glycoprotein substrate	-	0.9409	94.09%
CYP3A4 substrate	+	0.5174	51.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7873	78.73%
CYP3A4 inhibition	-	0.5571	55.71%
CYP2C9 inhibition	+	0.7766	77.66%
CYP2C19 inhibition	+	0.8962	89.62%
CYP2D6 inhibition	-	0.7334	73.34%
CYP1A2 inhibition	+	0.8679	86.79%
CYP2C8 inhibition	+	0.6337	63.37%
CYP inhibitory promiscuity	+	0.7750	77.50%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6135	61.35%
Eye corrosion	-	0.9782	97.82%
Eye irritation	+	0.6660	66.60%
Skin irritation	-	0.6511	65.11%
Skin corrosion	-	0.9662	96.62%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6263	62.63%
Micronuclear	+	0.9200	92.00%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.9410	94.10%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.4559	45.59%
Acute Oral Toxicity (c)	III	0.5602	56.02%
Estrogen receptor binding	+	0.5913	59.13%
Androgen receptor binding	-	0.5331	53.31%
Thyroid receptor binding	+	0.6023	60.23%
Glucocorticoid receptor binding	+	0.6900	69.00%
Aromatase binding	-	0.6102	61.02%
PPAR gamma	+	0.6783	67.83%
Honey bee toxicity	-	0.9065	90.65%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.8898	88.98%

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	97.85%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.37%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.57%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.70%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.49%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.25%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	89.81%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.17%	99.23%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.45%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.43%	99.17%
CHEMBL2581	P07339	Cathepsin D	82.27%	98.95%
CHEMBL2535	P11166	Glucose transporter	82.06%	98.75%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.41%	99.15%

Plants that contains it

• Muntingia calabura

Cross-Links

• PubChem: 145706492
• LOTUS: LTS0027966
• wikiData: Q104912767