(2S)-2-[3,4-dihydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]-5,7-dihydroxy-2,3-dihydrochromen-4-one

Details

• Internal ID: 3cedb9ed-23cf-4fbd-8620-ee4f2fec113b
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
• IUPAC Name: (2S)-2-[3,4-dihydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]-5,7-dihydroxy-2,3-dihydrochromen-4-one
• InChI: InChI=1S/C25H28O7/c1-12(2)5-6-13-7-14(8-16-22(29)24(30)25(3,4)32-23(13)16)19-11-18(28)21-17(27)9-15(26)10-20(21)31-19/h5,7-10,19,22,24,26-27,29-30H,6,11H2,1-4H3/t19-,22?,24?/m0/s1
• InChI Key: KYGXFLIBLYFPAZ-HRRASNIPSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₇
• Molecular Weight: 440.50 g/mol
• Exact Mass: 440.18350323 g/mol
• Topological Polar Surface Area (TPSA): 116.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.88
• H-Bond Acceptor: 7
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• BDBM50274942
• (2S)-3'',4'',5,7-tetrahydroxy-2'',2''-dimethyl-8''-(3-methylbut-2-enyl)-2,6''-bichroman-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9529	95.29%
Caco-2	-	0.6224	62.24%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6804	68.04%
OATP2B1 inhibitior	-	0.5787	57.87%
OATP1B1 inhibitior	+	0.8823	88.23%
OATP1B3 inhibitior	+	0.9783	97.83%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8802	88.02%
P-glycoprotein inhibitior	+	0.6146	61.46%
P-glycoprotein substrate	-	0.6071	60.71%
CYP3A4 substrate	+	0.6478	64.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7927	79.27%
CYP3A4 inhibition	-	0.7783	77.83%
CYP2C9 inhibition	+	0.6597	65.97%
CYP2C19 inhibition	+	0.6948	69.48%
CYP2D6 inhibition	-	0.8230	82.30%
CYP1A2 inhibition	-	0.7149	71.49%
CYP2C8 inhibition	+	0.5326	53.26%
CYP inhibitory promiscuity	+	0.6996	69.96%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6277	62.77%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.8564	85.64%
Skin irritation	-	0.7210	72.10%
Skin corrosion	-	0.9131	91.31%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6930	69.30%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.7589	75.89%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7975	79.75%
Acute Oral Toxicity (c)	III	0.5497	54.97%
Estrogen receptor binding	+	0.8706	87.06%
Androgen receptor binding	+	0.6318	63.18%
Thyroid receptor binding	-	0.5242	52.42%
Glucocorticoid receptor binding	+	0.8429	84.29%
Aromatase binding	+	0.6157	61.57%
PPAR gamma	+	0.8029	80.29%
Honey bee toxicity	-	0.6828	68.28%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9824	98.24%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	19000 nM	IC50	PMID: 23672185

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.72%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.67%	94.45%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.43%	96.12%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.76%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.18%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.21%	85.14%
CHEMBL2581	P07339	Cathepsin D	89.49%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	89.08%	83.82%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.32%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.31%	99.23%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	87.53%	93.40%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.48%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.90%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	86.71%	94.73%
CHEMBL4208	P20618	Proteasome component C5	83.55%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.12%	95.89%
CHEMBL236	P41143	Delta opioid receptor	82.87%	99.35%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	81.40%	93.10%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	80.48%	95.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.36%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.18%	92.62%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.16%	80.00%

Plants that contains it

• Erythrina abyssinica
• Erythrina abyssinica

Cross-Links

• PubChem: 44589218
• NPASS: NPC474023
• ChEMBL: CHEMBL458619
• LOTUS: LTS0272263
• wikiData: Q105147718