(2S)-5,7-dihydroxy-2-[3-(3-hydroxy-3-methylbutyl)-4-methoxyphenyl]-8-[(1E)-3-methylbuta-1,3-dienyl]-2,3-dihydrochromen-4-one

Details

• Internal ID: 6ee9b801-105c-4528-becd-b8384c5c3afd
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
• IUPAC Name: (2S)-5,7-dihydroxy-2-[3-(3-hydroxy-3-methylbutyl)-4-methoxyphenyl]-8-[(1E)-3-methylbuta-1,3-dienyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=C)C=CC1=C2C(=C(C=C1O)O)C(=O)CC(O2)C3=CC(=C(C=C3)OC)CCC(C)(C)O
• SMILES (Isomeric): CC(=C)/C=C/C1=C2C(=C(C=C1O)O)C(=O)C[C@H](O2)C3=CC(=C(C=C3)OC)CCC(C)(C)O
• InChI: InChI=1S/C26H30O6/c1-15(2)6-8-18-19(27)13-20(28)24-21(29)14-23(32-25(18)24)16-7-9-22(31-5)17(12-16)10-11-26(3,4)30/h6-9,12-13,23,27-28,30H,1,10-11,14H2,2-5H3/b8-6+/t23-/m0/s1
• InChI Key: ZKIWCYIIXDCABS-DRGXBFSJSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₆
• Molecular Weight: 438.50 g/mol
• Exact Mass: 438.20423867 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.11
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9805	98.05%
Caco-2	+	0.5314	53.14%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.6678	66.78%
OATP2B1 inhibitior	-	0.8588	85.88%
OATP1B1 inhibitior	+	0.8609	86.09%
OATP1B3 inhibitior	+	0.8784	87.84%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9234	92.34%
P-glycoprotein inhibitior	+	0.6983	69.83%
P-glycoprotein substrate	-	0.5404	54.04%
CYP3A4 substrate	+	0.6476	64.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8230	82.30%
CYP3A4 inhibition	+	0.6217	62.17%
CYP2C9 inhibition	+	0.5923	59.23%
CYP2C19 inhibition	+	0.6141	61.41%
CYP2D6 inhibition	-	0.7984	79.84%
CYP1A2 inhibition	+	0.6463	64.63%
CYP2C8 inhibition	+	0.6453	64.53%
CYP inhibitory promiscuity	+	0.6371	63.71%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6994	69.94%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8191	81.91%
Skin irritation	-	0.7392	73.92%
Skin corrosion	-	0.9231	92.31%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6500	65.00%
Micronuclear	-	0.7200	72.00%
Hepatotoxicity	-	0.6676	66.76%
skin sensitisation	-	0.8011	80.11%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5595	55.95%
Acute Oral Toxicity (c)	III	0.3892	38.92%
Estrogen receptor binding	+	0.8720	87.20%
Androgen receptor binding	+	0.7488	74.88%
Thyroid receptor binding	+	0.7328	73.28%
Glucocorticoid receptor binding	+	0.8311	83.11%
Aromatase binding	+	0.6073	60.73%
PPAR gamma	+	0.8318	83.18%
Honey bee toxicity	-	0.6630	66.30%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9894	98.94%

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	99.23%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.95%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.91%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.53%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.76%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.26%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.72%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.41%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	88.82%	94.73%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.76%	93.99%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.02%	95.89%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.78%	96.95%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	86.11%	86.92%
CHEMBL1951	P21397	Monoamine oxidase A	85.52%	91.49%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.10%	96.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.71%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.57%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.71%	92.62%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	82.97%	92.68%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.40%	92.94%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.99%	97.14%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.61%	99.17%

Plants that contains it

• Azadirachta indica

Cross-Links

• PubChem: 163187092
• LOTUS: LTS0134495
• wikiData: Q105378495