5,7-Dihydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one

Details

• Internal ID: 3fb131bd-527f-48b5-907a-f41a15a8f7de
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 3-prenylated flavans > 3-prenylated flavanones
• IUPAC Name: 5,7-dihydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)C2CC(=O)C3=C(C=C(C=C3O2)O)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=CC(=C1O)CC=C(C)C)C2CC(=O)C3=C(C=C(C=C3O2)O)O)C
• InChI: InChI=1S/C25H28O5/c1-14(2)5-7-16-9-18(10-17(25(16)29)8-6-15(3)4)22-13-21(28)24-20(27)11-19(26)12-23(24)30-22/h5-6,9-12,22,26-27,29H,7-8,13H2,1-4H3
• InChI Key: LQHKFMYWTKORCE-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₅
• Molecular Weight: 408.50 g/mol
• Exact Mass: 408.19367399 g/mol
• Topological Polar Surface Area (TPSA): 87.00 Ų
• XlogP: 6.20
• Atomic LogP (AlogP): 5.53
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• 77263-11-7
• NSC618154
• NSC 618154
• CHEMBL454332
• NSC-618154
• 5,7,4'-trihydroxy-3',5'-diprenylflavanone
• 4H-1-Benzopyran-4-one,3-Dihydro-5,7-dihydroxy-2-[4-hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-, (S)-
• 4H-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl)-, (S)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9858	98.58%
Caco-2	+	0.5642	56.42%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.7773	77.73%
OATP2B1 inhibitior	-	0.5787	57.87%
OATP1B1 inhibitior	+	0.9004	90.04%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9047	90.47%
P-glycoprotein inhibitior	+	0.6387	63.87%
P-glycoprotein substrate	-	0.8327	83.27%
CYP3A4 substrate	+	0.5430	54.30%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	-	0.6496	64.96%
CYP2C9 inhibition	+	0.7915	79.15%
CYP2C19 inhibition	+	0.8710	87.10%
CYP2D6 inhibition	-	0.6886	68.86%
CYP1A2 inhibition	+	0.8277	82.77%
CYP2C8 inhibition	-	0.7055	70.55%
CYP inhibitory promiscuity	+	0.8858	88.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.7154	71.54%
Eye corrosion	-	0.9915	99.15%
Eye irritation	-	0.5243	52.43%
Skin irritation	-	0.7533	75.33%
Skin corrosion	-	0.9404	94.04%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7443	74.43%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5803	58.03%
skin sensitisation	-	0.7764	77.64%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4917	49.17%
Acute Oral Toxicity (c)	III	0.4222	42.22%
Estrogen receptor binding	+	0.9252	92.52%
Androgen receptor binding	+	0.6787	67.87%
Thyroid receptor binding	+	0.6501	65.01%
Glucocorticoid receptor binding	+	0.8657	86.57%
Aromatase binding	+	0.5678	56.78%
PPAR gamma	+	0.8926	89.26%
Honey bee toxicity	-	0.8106	81.06%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9943	99.43%

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	99.57%	91.11%
CHEMBL1929	P47989	Xanthine dehydrogenase	95.11%	96.12%
CHEMBL2581	P07339	Cathepsin D	93.94%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.70%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.52%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	90.54%	94.73%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.22%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.15%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	87.95%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.30%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.39%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.29%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	85.77%	85.14%
CHEMBL4208	P20618	Proteasome component C5	85.50%	90.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.12%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.51%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.99%	99.17%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.17%	83.10%

Plants that contains it

• Azadirachta indica
• Erythrina abyssinica
• Erythrina addisoniae
• Erythrina burttii
• Erythrina mildbraedii
• Erythrina sigmoidea
• Erythrina variegata

Cross-Links

• PubChem: 101203
• LOTUS: LTS0270471
• wikiData: Q105155551