Bonannione A

Details

• Internal ID: 52b60b12-c593-4f66-8e7e-9aaa67b55129
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 6-prenylated flavans > 6-prenylated flavanones
• IUPAC Name: (2S)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)C3=CC=C(C=C3)O)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC=C(C=C3)O)O)/C)C
• InChI: InChI=1S/C25H28O5/c1-15(2)5-4-6-16(3)7-12-19-20(27)13-23-24(25(19)29)21(28)14-22(30-23)17-8-10-18(26)11-9-17/h5,7-11,13,22,26-27,29H,4,6,12,14H2,1-3H3/b16-7+/t22-/m0/s1
• InChI Key: XYIQIBWIEGCVQY-RWHUQTJRSA-N
• Popularity: 15 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): 5.75
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• 6-Geranylnaringenin
• 97126-57-3
• Mimulone
• (2S)-6-[(2E)-3,7-dimethylocta-2,6-dienyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• 4H-1-benzopyran-4-one, 6-[(2E)-3,7-dimethyl-2,6-octadienyl]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-
• CHEMBL374130
• SCHEMBL12780391
• SCHEMBL16105830
• DTXSID10420836
• BDBM50380198
• 4H-1-Benzopyran-4-one, 6-(3,7-dimethyl-2,6-octadienyl)-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, [S-(E)]-
• 4H-1-Benzopyran-4-one, 6-[(2E)-3,7-dimethyl-2,6-octadienyl]-2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9806	98.06%
Caco-2	-	0.7584	75.84%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7635	76.35%
OATP2B1 inhibitior	-	0.5799	57.99%
OATP1B1 inhibitior	+	0.8510	85.10%
OATP1B3 inhibitior	+	0.9047	90.47%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9115	91.15%
P-glycoprotein inhibitior	+	0.6656	66.56%
P-glycoprotein substrate	-	0.7766	77.66%
CYP3A4 substrate	+	0.5927	59.27%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.7912	79.12%
CYP3A4 inhibition	+	0.6469	64.69%
CYP2C9 inhibition	-	0.5737	57.37%
CYP2C19 inhibition	+	0.6029	60.29%
CYP2D6 inhibition	-	0.7971	79.71%
CYP1A2 inhibition	+	0.8258	82.58%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.7323	73.23%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.7560	75.60%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.6482	64.82%
Skin irritation	-	0.7522	75.22%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	-	0.5054	50.54%
Human Ether-a-go-go-Related Gene inhibition	-	0.3642	36.42%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7893	78.93%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.6898	68.98%
Acute Oral Toxicity (c)	III	0.3582	35.82%
Estrogen receptor binding	+	0.8964	89.64%
Androgen receptor binding	+	0.7518	75.18%
Thyroid receptor binding	+	0.6621	66.21%
Glucocorticoid receptor binding	+	0.7997	79.97%
Aromatase binding	+	0.5943	59.43%
PPAR gamma	+	0.8723	87.23%
Honey bee toxicity	-	0.8251	82.51%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	1.0000	100.00%

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	99.47%	91.11%
CHEMBL2581	P07339	Cathepsin D	96.67%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.12%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.69%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	93.04%	94.73%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.45%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.97%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.30%	95.56%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	87.81%	92.68%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	87.65%	90.71%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.48%	96.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.97%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.57%	99.17%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	84.89%	85.00%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	83.46%	93.10%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.46%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.41%	95.89%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.71%	85.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.69%	100.00%
CHEMBL4208	P20618	Proteasome component C5	81.88%	90.00%

Plants that contains it

• Artocarpus altilis
• Bonannia graeca
• Diplacus clevelandii
• Humulus lupulus
• Macaranga alnifolia
• Macaranga pleiostemon
• Paulownia tomentosa
• Schizolaena hystrix
• Sophora tomentosa

Cross-Links

• PubChem: 5716903
• NPASS: NPC228504
• ChEMBL: CHEMBL374130
• LOTUS: LTS0016846
• wikiData: Q82232130