1-Methoxyficifolinol

Details

• Internal ID: 042f8856-3ea2-47b7-95c8-83304e8c93a9
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > Furanoisoflavonoids > Pterocarpans
• IUPAC Name: (6aR,11aR)-1-methoxy-2,8-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
• SMILES (Canonical): CC(=CCC1=CC2=C(C=C1O)OC3C2COC4=C3C(=C(C(=C4)O)CC=C(C)C)OC)C
• SMILES (Isomeric): CC(=CCC1=CC2=C(C=C1O)O[C@@H]3[C@H]2COC4=C3C(=C(C(=C4)O)CC=C(C)C)OC)C
• InChI: InChI=1S/C26H30O5/c1-14(2)6-8-16-10-18-19-13-30-23-12-21(28)17(9-7-15(3)4)25(29-5)24(23)26(19)31-22(18)11-20(16)27/h6-7,10-12,19,26-28H,8-9,13H2,1-5H3/t19-,26+/m0/s1
• InChI Key: WIEKYGJSRGBBTQ-AFMDSPMNSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₀O₅
• Molecular Weight: 422.50 g/mol
• Exact Mass: 422.20932405 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 6.10
• Atomic LogP (AlogP): 5.73
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

• U4JQ9U5MEF
• CHEMBL4647021
• CHEBI:69096
• 129280-35-9
• (6aR,11aR)-1-Methoxy-2,8-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-(1)benzofuro(3,2-C)chromene-3,9-diol
• (6aR,11aR)-6a,11a-Dihydro-1-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-6H-benzofuro(3,2-C)(1)benzopyran-3,9-diol
• 6H-Benzofuro(3,2-C)(1)benzopyran-3,9-diol, 6a,11a-dihydro-1-methoxy-2,8-bis(3-methyl-2-buten-1-yl)-, (6aR,11aR)-
• 6H-Benzofuro(3,2-C)(1)benzopyran-3,9-diol, 6a,11a-dihydro-1-methoxy-2,8-bis(3-methyl-2-butenyl)-, (6ar-cis)-
• (6ar,11ar)-1-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6h-[1]benzofuro[3,2-c]chromene-3,9-diol
• (6aR,11aR)-1-methoxy-2,8-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromene-3,9-diol
• (6aR,11aR)-1-Methoxy-8-(3-methyl-but-2-enyl)-2-(3-methyl-but-2-enyl)-6a,11a-dihydro-6H-benzofuro[3,2-c][1]benzopyran-3,9-diol
• 3,9-Dihydroxy-1-methoxy-2,8-diprenylpterocarpan
• (6aR,11aR)-1-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-6a,11a-dihydro-6H-(1)benzofuro(3,2-c)chromene-3,9-diol
• (6aR,11aR)-1-methoxy-8-(3-methyl-but-2-enyl)-2-(3-methyl-but-2-enyl)-6a,11a-dihydro-6H-benzofuro(3,2-c)(1)benzopyran-3,9-diol
• UNII-U4JQ9U5MEF
• DTXSID901315138
• BDBM50539737
• Q27137437
• (6aR,11aR)-1-methoxy-2,8-bis(3-methylbut-2-enyl)-6a,11a-dihydro-6H-benzofuro[3,2-c]chromene-3,9-diol
• 6H-benzofuro[3,2-c][1]benzopyran-3,9-diol, 6a,11a-dihydro-1-methoxy-2,8-bis(3-methyl-2-butenyl)-, (6aR,11aR)-
• InChI=1/C26H30O5/c1-14(2)6-8-16-10-18-19-13-30-23-12-21(28)17(9-7-15(3)4)25(29-5)24(23)26(19)31-22(18)11-20(16)27/h6-7,10-12,19,26-28H,8-9,13H2,1-5H3/t19-,26+/m0/s
• rel-(6aR,11aR)-1-methoxy-2,8-bis(3-methylbut-2-en-1-yl)-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	+	0.9890	98.90%
Caco-2	+	0.6519	65.19%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7839	78.39%
OATP2B1 inhibitior	-	0.8652	86.52%
OATP1B1 inhibitior	+	0.8801	88.01%
OATP1B3 inhibitior	+	0.9193	91.93%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.9810	98.10%
P-glycoprotein inhibitior	+	0.7898	78.98%
P-glycoprotein substrate	-	0.6886	68.86%
CYP3A4 substrate	+	0.5729	57.29%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	+	0.4888	48.88%
CYP3A4 inhibition	-	0.5207	52.07%
CYP2C9 inhibition	+	0.8028	80.28%
CYP2C19 inhibition	+	0.8660	86.60%
CYP2D6 inhibition	-	0.5857	58.57%
CYP1A2 inhibition	+	0.8968	89.68%
CYP2C8 inhibition	+	0.5393	53.93%
CYP inhibitory promiscuity	+	0.9134	91.34%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6417	64.17%
Eye corrosion	-	0.9901	99.01%
Eye irritation	-	0.8055	80.55%
Skin irritation	-	0.8083	80.83%
Skin corrosion	-	0.9520	95.20%
Ames mutagenesis	+	0.5946	59.46%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	-	0.6250	62.50%
skin sensitisation	-	0.7483	74.83%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7210	72.10%
Acute Oral Toxicity (c)	III	0.6258	62.58%
Estrogen receptor binding	+	0.9096	90.96%
Androgen receptor binding	+	0.6700	67.00%
Thyroid receptor binding	+	0.7193	71.93%
Glucocorticoid receptor binding	+	0.7883	78.83%
Aromatase binding	-	0.5078	50.78%
PPAR gamma	+	0.8322	83.22%
Honey bee toxicity	-	0.8248	82.48%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9850	98.50%

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	99.66%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.09%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.77%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.16%	96.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.09%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.03%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.41%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.16%	86.33%
CHEMBL2581	P07339	Cathepsin D	85.52%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	84.76%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.37%	100.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.46%	96.95%
CHEMBL3192	Q9BY41	Histone deacetylase 8	82.08%	93.99%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.23%	95.56%

Plants that contains it

• Glycyrrhiza
• Glycyrrhiza aspera
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Glycyrrhiza uralensis
• Mitracarpus hirtus

Cross-Links

• PubChem: 480872
• NPASS: NPC62730
• LOTUS: LTS0082691
• wikiData: Q27137437