(2S)-5-hydroxy-8-[(E)-3-hydroxy-3-methylbut-1-enyl]-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one

Details

• Internal ID: 33da9f87-f77b-4433-a4c6-e2a2c05c7660
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > O-methylated flavonoids > 7-O-methylated flavonoids
• IUPAC Name: (2S)-5-hydroxy-8-[(E)-3-hydroxy-3-methylbut-1-enyl]-7-methoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(C)(C=CC1=C(C=C(C2=C1OC(CC2=O)C3=CC=CC=C3)O)OC)O
• SMILES (Isomeric): CC(C)(/C=C/C1=C(C=C(C2=C1O[C@@H](CC2=O)C3=CC=CC=C3)O)OC)O
• InChI: InChI=1S/C21H22O5/c1-21(2,24)10-9-14-18(25-3)12-16(23)19-15(22)11-17(26-20(14)19)13-7-5-4-6-8-13/h4-10,12,17,23-24H,11H2,1-3H3/b10-9+/t17-/m0/s1
• InChI Key: DTIQAJRSEBJNKG-FVNWOWOISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₂O₅
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9811	98.11%
Caco-2	+	0.7042	70.42%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8485	84.85%
OATP2B1 inhibitior	-	0.8621	86.21%
OATP1B1 inhibitior	+	0.8975	89.75%
OATP1B3 inhibitior	+	0.9767	97.67%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7606	76.06%
P-glycoprotein inhibitior	-	0.5275	52.75%
P-glycoprotein substrate	-	0.8790	87.90%
CYP3A4 substrate	+	0.5723	57.23%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	+	0.5737	57.37%
CYP2C9 inhibition	+	0.7020	70.20%
CYP2C19 inhibition	+	0.9053	90.53%
CYP2D6 inhibition	-	0.6085	60.85%
CYP1A2 inhibition	+	0.7061	70.61%
CYP2C8 inhibition	+	0.6433	64.33%
CYP inhibitory promiscuity	+	0.7786	77.86%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.4657	46.57%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.6170	61.70%
Skin irritation	-	0.7980	79.80%
Skin corrosion	-	0.9579	95.79%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4126	41.26%
Micronuclear	+	0.6159	61.59%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.9018	90.18%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5505	55.05%
Acute Oral Toxicity (c)	III	0.4712	47.12%
Estrogen receptor binding	+	0.7246	72.46%
Androgen receptor binding	+	0.6515	65.15%
Thyroid receptor binding	+	0.6852	68.52%
Glucocorticoid receptor binding	+	0.7885	78.85%
Aromatase binding	-	0.5000	50.00%
PPAR gamma	+	0.8463	84.63%
Honey bee toxicity	-	0.8204	82.04%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9588	95.88%

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	98.63%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.23%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.36%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.29%	85.14%
CHEMBL2581	P07339	Cathepsin D	93.91%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.80%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.83%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	87.84%	94.73%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.17%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.13%	99.23%
CHEMBL2535	P11166	Glucose transporter	84.34%	98.75%

Plants that contains it

• Tephrosia leiocarpa

Cross-Links

• PubChem: 15714483
• LOTUS: LTS0268848
• wikiData: Q104988815