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

Details

• Internal ID: 330734b3-1e45-40e0-822e-0ad1020d05ba
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 2-prenylated flavans > 2-prenylated flavanones
• IUPAC Name: (2S)-5,7-dihydroxy-2-[8-hydroxy-2,2-dimethyl-5-(3-methylbut-2-enyl)chromen-6-yl]-2,3-dihydrochromen-4-one
• InChI: InChI=1S/C25H26O6/c1-13(2)5-6-15-16-7-8-25(3,4)31-24(16)20(29)11-17(15)21-12-19(28)23-18(27)9-14(26)10-22(23)30-21/h5,7-11,21,26-27,29H,6,12H2,1-4H3/t21-/m0/s1
• InChI Key: DOHUWPORVBGXGM-NRFANRHFSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₆O₆
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.17293854 g/mol
• Topological Polar Surface Area (TPSA): 96.20 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.20
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• BDBM50274831
• (S)-5,7,8''-trihydroxy-2'',2''-dimethyl-5''-(3-methylbut-2-enyl)-2,6''-bichroman-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9744	97.44%
Caco-2	+	0.5141	51.41%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7156	71.56%
OATP2B1 inhibitior	-	0.8604	86.04%
OATP1B1 inhibitior	+	0.8547	85.47%
OATP1B3 inhibitior	+	0.9618	96.18%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8998	89.98%
P-glycoprotein inhibitior	+	0.6520	65.20%
P-glycoprotein substrate	-	0.5349	53.49%
CYP3A4 substrate	+	0.6461	64.61%
CYP2C9 substrate	-	0.7981	79.81%
CYP2D6 substrate	-	0.8063	80.63%
CYP3A4 inhibition	-	0.7798	77.98%
CYP2C9 inhibition	+	0.6814	68.14%
CYP2C19 inhibition	+	0.7291	72.91%
CYP2D6 inhibition	-	0.8150	81.50%
CYP1A2 inhibition	-	0.6805	68.05%
CYP2C8 inhibition	+	0.5625	56.25%
CYP inhibitory promiscuity	+	0.7838	78.38%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6571	65.71%
Eye corrosion	-	0.9916	99.16%
Eye irritation	-	0.6666	66.66%
Skin irritation	-	0.7286	72.86%
Skin corrosion	-	0.9305	93.05%
Ames mutagenesis	-	0.5615	56.15%
Human Ether-a-go-go-Related Gene inhibition	+	0.7299	72.99%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.7671	76.71%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.5871	58.71%
Acute Oral Toxicity (c)	III	0.4504	45.04%
Estrogen receptor binding	+	0.8488	84.88%
Androgen receptor binding	+	0.6252	62.52%
Thyroid receptor binding	+	0.6534	65.34%
Glucocorticoid receptor binding	+	0.8649	86.49%
Aromatase binding	-	0.4903	49.03%
PPAR gamma	+	0.7970	79.70%
Honey bee toxicity	-	0.6887	68.87%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9884	98.84%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	13900 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	99.78%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.74%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.40%	98.95%
CHEMBL1929	P47989	Xanthine dehydrogenase	94.99%	96.12%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.75%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.95%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.04%	89.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	89.60%	93.40%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.73%	99.23%
CHEMBL4208	P20618	Proteasome component C5	87.68%	90.00%
CHEMBL3401	O75469	Pregnane X receptor	87.28%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.91%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.32%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.15%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.15%	95.89%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	85.12%	95.71%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	85.03%	80.00%
CHEMBL226	P30542	Adenosine A1 receptor	85.02%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.78%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.54%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.07%	90.71%
CHEMBL2535	P11166	Glucose transporter	80.11%	98.75%

Plants that contains it

• Erythrina abyssinica
• Erythrina abyssinica

Cross-Links

• PubChem: 44589106
• NPASS: NPC186686
• ChEMBL: CHEMBL458936
• LOTUS: LTS0239511
• wikiData: Q104985996