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

Details

• Internal ID: 6550bae9-6a9c-4918-bde6-5c4330c302fc
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
• IUPAC Name: (2S)-5,7-dihydroxy-2-[3-hydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-3,4-dihydrochromen-6-yl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=CC(=CC2=C1OC(C(C2)O)(C)C)C3CC(=O)C4=C(C=C(C=C4O3)O)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=CC2=C1OC(C(C2)O)(C)C)[C@@H]3CC(=O)C4=C(C=C(C=C4O3)O)O)C
• InChI: InChI=1S/C25H28O6/c1-13(2)5-6-14-7-15(8-16-9-22(29)25(3,4)31-24(14)16)20-12-19(28)23-18(27)10-17(26)11-21(23)30-20/h5,7-8,10-11,20,22,26-27,29H,6,9,12H2,1-4H3/t20-,22?/m0/s1
• InChI Key: WJBWITXUNBMVLF-AIBWNMTMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₆
• Molecular Weight: 424.50 g/mol
• Exact Mass: 424.18858861 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 4.70
• Atomic LogP (AlogP): 4.39
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• BDBM50274874
• (2S)-3'',5,7-trihydroxy-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	+	0.9805	98.05%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.6517	65.17%
OATP2B1 inhibitior	-	0.7202	72.02%
OATP1B1 inhibitior	+	0.8799	87.99%
OATP1B3 inhibitior	+	0.9643	96.43%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.8538	85.38%
P-glycoprotein inhibitior	+	0.6148	61.48%
P-glycoprotein substrate	-	0.6280	62.80%
CYP3A4 substrate	+	0.6462	64.62%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7812	78.12%
CYP3A4 inhibition	-	0.7542	75.42%
CYP2C9 inhibition	+	0.5421	54.21%
CYP2C19 inhibition	+	0.6224	62.24%
CYP2D6 inhibition	-	0.8052	80.52%
CYP1A2 inhibition	-	0.7431	74.31%
CYP2C8 inhibition	+	0.4858	48.58%
CYP inhibitory promiscuity	+	0.6337	63.37%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6343	63.43%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.8388	83.88%
Skin irritation	-	0.7192	71.92%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7550	75.50%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	-	0.5822	58.22%
skin sensitisation	-	0.7627	76.27%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.6307	63.07%
Acute Oral Toxicity (c)	III	0.3911	39.11%
Estrogen receptor binding	+	0.9232	92.32%
Androgen receptor binding	+	0.6478	64.78%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.8978	89.78%
Aromatase binding	+	0.6673	66.73%
PPAR gamma	+	0.8455	84.55%
Honey bee toxicity	-	0.6991	69.91%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9832	98.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	14900 nM	IC50	PMID: 11908979

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.75%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	98.55%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.69%	94.45%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.16%	96.12%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.19%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.57%	85.14%
CHEMBL236	P41143	Delta opioid receptor	91.71%	99.35%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.03%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.82%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.08%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.84%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.62%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	88.99%	94.73%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.60%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.90%	99.23%
CHEMBL4208	P20618	Proteasome component C5	85.18%	90.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.90%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.02%	95.89%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.91%	93.40%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	83.62%	80.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	82.90%	95.71%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	81.75%	92.68%

Plants that contains it

• Erythrina abyssinica
• Erythrina abyssinica

Cross-Links

• PubChem: 44589132
• NPASS: NPC474021
• ChEMBL: CHEMBL458555
• LOTUS: LTS0252897
• wikiData: Q105306670