2alpha-Phenyl-6-[(E)-3,7-dimethyl-2,6-octadienyl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one

Details

• Internal ID: 1c9f4aee-4787-4e9e-8e7b-d7399edae8b0
• 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-phenyl-2,3-dihydrochromen-4-one
• SMILES (Canonical): CC(=CCCC(=CCC1=C(C2=C(C=C1O)OC(CC2=O)C3=CC=CC=C3)O)C)C
• SMILES (Isomeric): CC(=CCC/C(=C/CC1=C(C2=C(C=C1O)O[C@@H](CC2=O)C3=CC=CC=C3)O)/C)C
• InChI: InChI=1S/C25H28O4/c1-16(2)8-7-9-17(3)12-13-19-20(26)14-23-24(25(19)28)21(27)15-22(29-23)18-10-5-4-6-11-18/h4-6,8,10-12,14,22,26,28H,7,9,13,15H2,1-3H3/b17-12+/t22-/m0/s1
• InChI Key: OLMVUAUNXUAIHB-PFSBYRDKSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₈O₄
• Molecular Weight: 392.50 g/mol
• Exact Mass: 392.19875937 g/mol
• Topological Polar Surface Area (TPSA): 66.80 Ų
• XlogP: 6.50
• Atomic LogP (AlogP): 6.04
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 6

Synonyms

• 2alpha-Phenyl-6-[(E)-3,7-dimethyl-2,6-octadienyl]-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9806	98.06%
Caco-2	-	0.7254	72.54%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.7635	76.35%
OATP2B1 inhibitior	-	0.7214	72.14%
OATP1B1 inhibitior	+	0.8812	88.12%
OATP1B3 inhibitior	+	0.9047	90.47%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9322	93.22%
P-glycoprotein inhibitior	+	0.7809	78.09%
P-glycoprotein substrate	-	0.8372	83.72%
CYP3A4 substrate	+	0.5565	55.65%
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	+	0.5205	52.05%
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	-	0.7905	79.05%
Skin irritation	-	0.7522	75.22%
Skin corrosion	-	0.9378	93.78%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8250	82.50%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.7893	78.93%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.7370	73.70%
Acute Oral Toxicity (c)	III	0.3582	35.82%
Estrogen receptor binding	+	0.9078	90.78%
Androgen receptor binding	+	0.6411	64.11%
Thyroid receptor binding	+	0.6265	62.65%
Glucocorticoid receptor binding	+	0.7871	78.71%
Aromatase binding	+	0.5801	58.01%
PPAR gamma	+	0.8836	88.36%
Honey bee toxicity	-	0.8646	86.46%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	99.61%	91.11%
CHEMBL2581	P07339	Cathepsin D	97.57%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.39%	95.56%
CHEMBL3401	O75469	Pregnane X receptor	93.29%	94.73%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.67%	85.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.95%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.39%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.21%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.63%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.31%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.76%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.34%	97.09%

Plants that contains it

• Amorphophallus konjac
• Aniba santalodora
• Astragalus circassicus
• Beilschmiedia madang
• Bethencourtia palmensis
• Boesenbergia rotunda
• Boswellia ovalifoliolata
• Campanula bayerniana
• Caucasalia pontica
• Centaurea scoparia
• Centaurea sphaerocephala subsp. sphaerocephala
• Colchicum filifolium
• Dacrycarpus dacrydioides
• Dialium excelsum
• Drymaria cordata
• Erythrina subumbrans
• Euphorbia hylonoma
• Hardenbergia violacea
• Heliotropium marifolium
• Helleborus niger subsp. macranthus
• Lepechinia urbanii
• Lindelofia anchusoides subsp. macrostyla
• Lonchocarpus chiricanus
• Maclura cochinchinensis
• Mentzelia decapetala
• Mimosa pigra
• Mucuna holtonii
• Oncosiphon sabulosus
• Pterocaulon serrulatum
• Pulsatilla chinensis
• Quercus marilandica
• Rubia argyi
• Salix rosmarinifolia
• Salvia lavanduloides
• Salvia patens
• Salvia virgata

Cross-Links

• PubChem: 44444915
• NPASS: NPC264160
• LOTUS: LTS0190425
• wikiData: Q105194040