(3R)-5,7-dihydroxy-3-[(S)-hydroxy(phenyl)methyl]-6-methoxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 69c244c6-a10f-446f-a69f-ad0290aa04d4
• Taxonomy: Phenylpropanoids and polyketides > Homoisoflavonoids > Homoisoflavans > Homoisoflavanones
• IUPAC Name: (3R)-5,7-dihydroxy-3-[(S)-hydroxy(phenyl)methyl]-6-methoxy-2,3-dihydrochromen-4-one
• SMILES (Canonical): COC1=C(C2=C(C=C1O)OCC(C2=O)C(C3=CC=CC=C3)O)O
• SMILES (Isomeric): COC1=C(C2=C(C=C1O)OC[C@@H](C2=O)[C@@H](C3=CC=CC=C3)O)O
• InChI: InChI=1S/C17H16O6/c1-22-17-11(18)7-12-13(16(17)21)15(20)10(8-23-12)14(19)9-5-3-2-4-6-9/h2-7,10,14,18-19,21H,8H2,1H3/t10-,14-/m1/s1
• InChI Key: HQZPRVYXHWQSHG-QMTHXVAHSA-N
• Popularity: 0 references 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): 96.20 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9391	93.91%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	+	0.5429	54.29%
Subcellular localzation	Mitochondria	0.5832	58.32%
OATP2B1 inhibitior	-	0.7225	72.25%
OATP1B1 inhibitior	+	0.9241	92.41%
OATP1B3 inhibitior	+	0.9268	92.68%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.7712	77.12%
P-glycoprotein inhibitior	-	0.7029	70.29%
P-glycoprotein substrate	-	0.8455	84.55%
CYP3A4 substrate	+	0.5077	50.77%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7814	78.14%
CYP3A4 inhibition	-	0.5658	56.58%
CYP2C9 inhibition	-	0.6206	62.06%
CYP2C19 inhibition	+	0.5793	57.93%
CYP2D6 inhibition	-	0.8112	81.12%
CYP1A2 inhibition	+	0.8681	86.81%
CYP2C8 inhibition	-	0.8632	86.32%
CYP inhibitory promiscuity	+	0.6063	60.63%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6934	69.34%
Eye corrosion	-	0.9736	97.36%
Eye irritation	-	0.5427	54.27%
Skin irritation	-	0.6862	68.62%
Skin corrosion	-	0.9491	94.91%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7518	75.18%
Micronuclear	+	0.8100	81.00%
Hepatotoxicity	-	0.5697	56.97%
skin sensitisation	-	0.8820	88.20%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.8821	88.21%
Acute Oral Toxicity (c)	III	0.7863	78.63%
Estrogen receptor binding	+	0.7007	70.07%
Androgen receptor binding	+	0.6606	66.06%
Thyroid receptor binding	-	0.4924	49.24%
Glucocorticoid receptor binding	+	0.6389	63.89%
Aromatase binding	-	0.7002	70.02%
PPAR gamma	-	0.4839	48.39%
Honey bee toxicity	-	0.8622	86.22%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.7797	77.97%

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	99.59%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.75%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.64%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.24%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.82%	99.15%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.68%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.52%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.36%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.50%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.40%	99.23%
CHEMBL2535	P11166	Glucose transporter	84.97%	98.75%
CHEMBL4208	P20618	Proteasome component C5	83.57%	90.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.07%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.58%	95.89%

Plants that contains it

• Persicaria ferruginea

Cross-Links

• PubChem: 26235906
• LOTUS: LTS0016810
• wikiData: Q105032528