Licorisoflavan A

Details

• Internal ID: cc521e43-3e82-49da-b8f6-2395ff1c520b
• Taxonomy: Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 7-O-methylated isoflavonoids
• IUPAC Name: 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1O)C2CC3=C(C(=C(C=C3OC2)OC)CC=C(C)C)OC)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1O)[C@H]2CC3=C(C(=C(C=C3OC2)OC)CC=C(C)C)OC)O)C
• InChI: InChI=1S/C27H34O5/c1-16(2)7-9-20-23(28)12-11-19(26(20)29)18-13-22-25(32-15-18)14-24(30-5)21(27(22)31-6)10-8-17(3)4/h7-8,11-12,14,18,28-29H,9-10,13,15H2,1-6H3/t18-/m0/s1
• InChI Key: GDAAEAXMNLVRCZ-SFHVURJKSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₄O₅
• Molecular Weight: 438.60 g/mol
• Exact Mass: 438.24062418 g/mol
• Topological Polar Surface Area (TPSA): 68.20 Ų
• XlogP: 6.80
• Atomic LogP (AlogP): 5.85
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 7

Synonyms

• 5-O-Methyllicoricidin
• 129314-37-0
• JW8U2YD8JL
• Licoriisoflavan A
• 7-O-Methyllicoricidin
• CHEBI:69083
• 7-O-METHYLLICORISOFLAVAN B
• (+)-7-O-METHYLLICORICIDIN
• 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
• 1,3-BENZENEDIOL, 4-((3R)-3,4-DIHYDRO-5,7-DIMETHOXY-6-(3-METHYL-2-BUTEN-1-YL)-2H-1-BENZOPYRAN-3-YL)-2-(3-METHYL-2-BUTEN-1-YL)-
• 4-((3R)-3,4-DIHYDRO-5,7-DIMETHOXY-6-(3-METHYL-2-BUTEN-1-YL)-2H-1-BENZOPYRAN-3-YL)-2-(3-METHYL-2-BUTEN-1-YL)-1,3-BENZENEDIOL
• LicorisoflavanA
• 4-((3R)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-3-yl)-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
• 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-en-1-yl)-3,4-dihydro-2H-chromen-3-yl]-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol
• UNII-JW8U2YD8JL
• CHEMBL4635007
• DTXSID40156136
• HY-N3385
• AKOS032949052
• NCGC00385627-01
• CS-0024064
• Q27137422
• 4-[(3R)-5,7-dimethoxy-6-(3-methylbut-2-enyl)chroman-3-yl]-2-(3-methylbut-2-enyl)benzene-1,3-diol
• 4-[(R)-5,7-Dimethoxy-6-(3-methyl-but-2-enyl)-1-benzopyran-3-yl]-2-((E)-3-methyl-but-2-enyl)-benzene-1,3-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9657	96.57%
Caco-2	+	0.6636	66.36%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.7468	74.68%
OATP2B1 inhibitior	-	0.8628	86.28%
OATP1B1 inhibitior	+	0.9232	92.32%
OATP1B3 inhibitior	+	0.9224	92.24%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9744	97.44%
P-glycoprotein inhibitior	+	0.7919	79.19%
P-glycoprotein substrate	-	0.5677	56.77%
CYP3A4 substrate	+	0.5934	59.34%
CYP2C9 substrate	-	0.6036	60.36%
CYP2D6 substrate	+	0.4888	48.88%
CYP3A4 inhibition	-	0.7310	73.10%
CYP2C9 inhibition	+	0.7765	77.65%
CYP2C19 inhibition	+	0.8637	86.37%
CYP2D6 inhibition	-	0.5398	53.98%
CYP1A2 inhibition	+	0.8762	87.62%
CYP2C8 inhibition	+	0.6823	68.23%
CYP inhibitory promiscuity	+	0.9195	91.95%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7717	77.17%
Eye corrosion	-	0.9889	98.89%
Eye irritation	-	0.8238	82.38%
Skin irritation	-	0.8179	81.79%
Skin corrosion	-	0.9456	94.56%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3973	39.73%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8377	83.77%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.8222	82.22%
Acute Oral Toxicity (c)	III	0.5623	56.23%
Estrogen receptor binding	+	0.8952	89.52%
Androgen receptor binding	+	0.7134	71.34%
Thyroid receptor binding	+	0.7193	71.93%
Glucocorticoid receptor binding	+	0.7551	75.51%
Aromatase binding	-	0.5470	54.70%
PPAR gamma	+	0.7902	79.02%
Honey bee toxicity	-	0.8074	80.74%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9921	99.21%

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%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.54%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.30%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.79%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.90%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.38%	95.89%
CHEMBL2581	P07339	Cathepsin D	90.07%	98.95%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	88.96%	93.40%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.19%	99.15%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.27%	100.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.04%	89.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.81%	89.00%
CHEMBL2535	P11166	Glucose transporter	85.52%	98.75%
CHEMBL4306	P22460	Voltage-gated potassium channel subunit Kv1.5	84.48%	94.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.74%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.96%	97.09%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	81.73%	98.11%
CHEMBL4355	O14976	Serine/threonine-protein kinase GAK	81.64%	89.32%
CHEMBL3194	P02766	Transthyretin	81.07%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.37%	96.00%

Plants that contains it

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

Cross-Links

• PubChem: 196831
• NPASS: NPC103152
• LOTUS: LTS0163058
• wikiData: Q27137422