4-Prenylphaseollidin

Details

• Internal ID: f1697ec2-8dea-4494-a0e0-5d445e690220
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (6aR,11aR)-4,10-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
• SMILES (Canonical): CC(=CCC1=C(C=CC2=C1OC3C2COC4=C3C=CC(=C4CC=C(C)C)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC2=C1O[C@@H]3[C@H]2COC4=C3C=CC(=C4CC=C(C)C)O)O)C
• InChI: InChI=1S/C25H28O4/c1-14(2)5-7-17-21(26)12-10-19-23(17)28-13-20-16-9-11-22(27)18(8-6-15(3)4)24(16)29-25(19)20/h5-6,9-12,20,25-27H,7-8,13H2,1-4H3/t20-,25-/m0/s1
• InChI Key: HOGHBEDTLGAJAS-CPJSRVTESA-N
• Popularity: 7 references 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): 58.90 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 5.72
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• CHEBI:65862
• (6aR,11aR)-4,10-bis(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
• (6aR,11aR-cis)-6a,11a-dihydro-4,10-bis(3-methyl-2-butenyl)-6H-benzofuro(3,2-c)(1)benzopyran-3,9-diol
• CHEMBL564141
• 4-(gamma,gamma-Dimethylallyl)-phaseollidin
• Q27134354
• (6aR,11aR)-4,10-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9932	99.32%
Caco-2	+	0.6323	63.23%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8433	84.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9216	92.16%
OATP1B3 inhibitior	+	0.9504	95.04%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9583	95.83%
P-glycoprotein inhibitior	+	0.7750	77.50%
P-glycoprotein substrate	-	0.7479	74.79%
CYP3A4 substrate	-	0.5258	52.58%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	+	0.4888	48.88%
CYP3A4 inhibition	-	0.6402	64.02%
CYP2C9 inhibition	+	0.8045	80.45%
CYP2C19 inhibition	+	0.8431	84.31%
CYP2D6 inhibition	-	0.6948	69.48%
CYP1A2 inhibition	+	0.8776	87.76%
CYP2C8 inhibition	-	0.7164	71.64%
CYP inhibitory promiscuity	+	0.8743	87.43%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6939	69.39%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.7090	70.90%
Skin irritation	-	0.7857	78.57%
Skin corrosion	-	0.9458	94.58%
Ames mutagenesis	+	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6654	66.54%
Micronuclear	-	0.5600	56.00%
Hepatotoxicity	+	0.5125	51.25%
skin sensitisation	-	0.7144	71.44%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.6297	62.97%
Acute Oral Toxicity (c)	III	0.5767	57.67%
Estrogen receptor binding	+	0.8986	89.86%
Androgen receptor binding	+	0.7662	76.62%
Thyroid receptor binding	+	0.6923	69.23%
Glucocorticoid receptor binding	+	0.7984	79.84%
Aromatase binding	+	0.5633	56.33%
PPAR gamma	+	0.8740	87.40%
Honey bee toxicity	-	0.9126	91.26%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9952	99.52%

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	98.72%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	92.09%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.87%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.54%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.67%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	86.17%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.01%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.97%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.75%	86.33%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.80%	93.40%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.61%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	81.45%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	80.52%	90.17%

Plants that contains it

• Erythrina burttii
• Erythrina latissima
• Erythrina lysistemon
• Erythrina mildbraedii
• Erythrina sigmoidea
• Erythrina subumbrans
• Erythrina zeyheri
• Lespedeza cyrtobotrya
• Lespedeza floribunda
• Peperomia blanda
• Teucrium betonicum

Cross-Links

• PubChem: 21141346
• NPASS: NPC129106
• ChEMBL: CHEMBL564141
• LOTUS: LTS0206210
• wikiData: Q105159811