Cajanone

Details

• Internal ID: 565aad49-cdb8-48ca-83aa-11ea887a5888
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Isoflavans > Isoflavanones > 3-prenylated isoflavanones
• IUPAC Name: 7-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-2,2-dimethyl-7,8-dihydropyrano[3,2-g]chromen-6-one
• SMILES (Canonical): CC(=CCC1=CC(=C(C=C1O)O)C2COC3=C(C2=O)C(=C4C=CC(OC4=C3)(C)C)O)C
• SMILES (Isomeric): CC(=CCC1=CC(=C(C=C1O)O)C2COC3=C(C2=O)C(=C4C=CC(OC4=C3)(C)C)O)C
• InChI: InChI=1S/C25H26O6/c1-13(2)5-6-14-9-16(19(27)10-18(14)26)17-12-30-21-11-20-15(7-8-25(3,4)31-20)23(28)22(21)24(17)29/h5,7-11,17,26-28H,6,12H2,1-4H3
• InChI Key: BAKSOIVZFARRJC-UHFFFAOYSA-N
• Popularity: 1 reference 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: 5.40
• Atomic LogP (AlogP): 4.86
• H-Bond Acceptor: 6
• H-Bond Donor: 3
• Rotatable Bonds: 3

Synonyms

• MHB9Z7D6GS
• 63006-48-4
• UNII-MHB9Z7D6GS
• NSC294409
• 2H,6H-Benzo(1,2-b:5,4-b')dipyran-6-one, 7-(2,4-dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl)-7,8-dihydro-5-hydroxy-2,2-dimethyl-
• 7-(2,4-Dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl)-7,8-dihydro-5-hydroxy-2,2-dimethyl-2H,6H-benzo(1,2-b:5,4-b')dipyran-6-one
• 7-[2,4-dihydroxy-5-(3-methylbut-2-enyl)phenyl]-5-hydroxy-2,2-dimethyl-7,8-dihydropyrano[3,2-g]chromen-6-one
• 7-[2,4-Dihydroxy-5-(3-methyl-2-buten-1-yl)phenyl]-7,8-dihydro-5-hydroxy-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one
• CHEMBL1968439
• CHEBI:175382
• DTXSID301104133
• LMPK12050495
• NSC-294409
• NCI60_002437
• 7-(2,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl)-5-hydroxy-2,2-dimethyl-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-6-one
• 7-[2,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-7,8-dihydro-5-hydroxy-2,2-dimethyl-2H,6H-benzo[1,2-b:5,4-b']dipyran-6-one, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9801	98.01%
Caco-2	-	0.5465	54.65%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8021	80.21%
OATP2B1 inhibitior	-	0.8591	85.91%
OATP1B1 inhibitior	+	0.8689	86.89%
OATP1B3 inhibitior	+	0.9278	92.78%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9748	97.48%
P-glycoprotein inhibitior	+	0.6705	67.05%
P-glycoprotein substrate	+	0.5668	56.68%
CYP3A4 substrate	+	0.6383	63.83%
CYP2C9 substrate	+	0.5979	59.79%
CYP2D6 substrate	-	0.8144	81.44%
CYP3A4 inhibition	-	0.8273	82.73%
CYP2C9 inhibition	+	0.8180	81.80%
CYP2C19 inhibition	+	0.8751	87.51%
CYP2D6 inhibition	-	0.8318	83.18%
CYP1A2 inhibition	+	0.7483	74.83%
CYP2C8 inhibition	-	0.6391	63.91%
CYP inhibitory promiscuity	+	0.8498	84.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7267	72.67%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.6468	64.68%
Skin irritation	-	0.7628	76.28%
Skin corrosion	-	0.9351	93.51%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4876	48.76%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.7923	79.23%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.6562	65.62%
Acute Oral Toxicity (c)	III	0.5584	55.84%
Estrogen receptor binding	+	0.9286	92.86%
Androgen receptor binding	+	0.7515	75.15%
Thyroid receptor binding	+	0.6752	67.52%
Glucocorticoid receptor binding	+	0.8750	87.50%
Aromatase binding	+	0.6952	69.52%
PPAR gamma	+	0.8843	88.43%
Honey bee toxicity	-	0.8351	83.51%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9922	99.22%

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	99.87%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.59%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.10%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.43%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.68%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.95%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.47%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	90.13%	96.61%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.34%	86.33%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.03%	90.71%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.78%	92.62%
CHEMBL1951	P21397	Monoamine oxidase A	87.56%	91.49%
CHEMBL1937	Q92769	Histone deacetylase 2	87.23%	94.75%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.18%	97.25%
CHEMBL4208	P20618	Proteasome component C5	86.91%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	86.87%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.01%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.96%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.49%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	83.34%	94.73%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	83.32%	93.40%
CHEMBL3038469	P24941	CDK2/Cyclin A	82.82%	91.38%
CHEMBL2413	P32246	C-C chemokine receptor type 1	82.47%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.02%	99.23%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.01%	93.99%

Plants that contains it

• Cajanus cajan
• Rhynchosia precatoria

Cross-Links

• PubChem: 325518
• LOTUS: LTS0185701
• wikiData: Q103813495