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

Details

• Internal ID: 96e780ba-de29-47ec-a6aa-852192ac390e
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (2S)-8-[(2S)-2-hydroxy-3-methylbut-3-enyl]-5,7-dimethoxy-2-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=C)C(CC1=C2C(=C(C=C1OC)OC)C(=O)CC(O2)C3=CC=CC=C3)O
• SMILES (Isomeric): CC(=C)[C@H](CC1=C2C(=C(C=C1OC)OC)C(=O)C[C@H](O2)C3=CC=CC=C3)O
• InChI: InChI=1S/C22H24O5/c1-13(2)16(23)10-15-19(25-3)12-20(26-4)21-17(24)11-18(27-22(15)21)14-8-6-5-7-9-14/h5-9,12,16,18,23H,1,10-11H2,2-4H3/t16-,18-/m0/s1
• InChI Key: RKAXZSIBGORDGB-WMZOPIPTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₄O₅
• Molecular Weight: 368.40 g/mol
• Exact Mass: 368.16237386 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.89
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9942	99.42%
Caco-2	+	0.7491	74.91%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6632	66.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8857	88.57%
OATP1B3 inhibitior	+	0.9176	91.76%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7303	73.03%
P-glycoprotein inhibitior	+	0.8447	84.47%
P-glycoprotein substrate	-	0.7505	75.05%
CYP3A4 substrate	+	0.5739	57.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6997	69.97%
CYP3A4 inhibition	-	0.5730	57.30%
CYP2C9 inhibition	-	0.6943	69.43%
CYP2C19 inhibition	+	0.6821	68.21%
CYP2D6 inhibition	-	0.8938	89.38%
CYP1A2 inhibition	+	0.5429	54.29%
CYP2C8 inhibition	+	0.5875	58.75%
CYP inhibitory promiscuity	+	0.7329	73.29%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9513	95.13%
Carcinogenicity (trinary)	Non-required	0.7113	71.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8385	83.85%
Skin irritation	-	0.7590	75.90%
Skin corrosion	-	0.9623	96.23%
Ames mutagenesis	-	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5240	52.40%
Micronuclear	-	0.5141	51.41%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7997	79.97%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6500	65.00%
Nephrotoxicity	-	0.5913	59.13%
Acute Oral Toxicity (c)	III	0.4991	49.91%
Estrogen receptor binding	+	0.7313	73.13%
Androgen receptor binding	-	0.4879	48.79%
Thyroid receptor binding	+	0.6611	66.11%
Glucocorticoid receptor binding	+	0.7156	71.56%
Aromatase binding	-	0.6696	66.96%
PPAR gamma	+	0.8000	80.00%
Honey bee toxicity	-	0.7264	72.64%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9823	98.23%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.96%	85.14%
CHEMBL2581	P07339	Cathepsin D	97.72%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.44%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.32%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.42%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.13%	86.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.90%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.58%	89.00%
CHEMBL2535	P11166	Glucose transporter	83.95%	98.75%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.72%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.08%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.94%	96.95%
CHEMBL3401	O75469	Pregnane X receptor	80.98%	94.73%

Plants that contains it

• Pongamia pinnata

Cross-Links

• PubChem: 11046839
• LOTUS: LTS0078284
• wikiData: Q105238283