(2E)-3-[4-({1,3-dihydroxy-1-[3-methoxy-4-(sulfooxy)phenyl]propan-2-yl}oxy)-3-methoxyphenyl]prop-2-enoic acid

Details

• Internal ID: 9b66db8a-aefb-4603-9582-8e6601a71ae8
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (E)-3-[4-[1,3-dihydroxy-1-(3-methoxy-4-sulfooxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]prop-2-enoic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)O)OC(CO)C(C2=CC(=C(C=C2)OS(=O)(=O)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O)OC(CO)C(C2=CC(=C(C=C2)OS(=O)(=O)O)OC)O
• InChI: InChI=1S/C20H22O11S/c1-28-16-9-12(4-8-19(22)23)3-6-14(16)30-18(11-21)20(24)13-5-7-15(17(10-13)29-2)31-32(25,26)27/h3-10,18,20-21,24H,11H2,1-2H3,(H,22,23)(H,25,26,27)/b8-4+
• InChI Key: KDEUQTJCZQGNJS-XBXARRHUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₁₁S
• Molecular Weight: 470.40 g/mol
• Exact Mass: 470.08828269 g/mol
• Topological Polar Surface Area (TPSA): 177.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.46
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 11

Synonyms

• CHEBI:91205
• Q27163124

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8840	88.40%
Caco-2	-	0.6926	69.26%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	+	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5877	58.77%
OATP2B1 inhibitior	-	0.7171	71.71%
OATP1B1 inhibitior	+	0.9128	91.28%
OATP1B3 inhibitior	+	0.9355	93.55%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.7588	75.88%
BSEP inhibitior	+	0.8085	80.85%
P-glycoprotein inhibitior	+	0.7258	72.58%
P-glycoprotein substrate	-	0.5530	55.30%
CYP3A4 substrate	+	0.5228	52.28%
CYP2C9 substrate	-	0.5971	59.71%
CYP2D6 substrate	-	0.8471	84.71%
CYP3A4 inhibition	-	0.9175	91.75%
CYP2C9 inhibition	-	0.7410	74.10%
CYP2C19 inhibition	-	0.7961	79.61%
CYP2D6 inhibition	-	0.9018	90.18%
CYP1A2 inhibition	-	0.6446	64.46%
CYP2C8 inhibition	-	0.5745	57.45%
CYP inhibitory promiscuity	-	0.8491	84.91%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	+	0.5989	59.89%
Carcinogenicity (trinary)	Non-required	0.6805	68.05%
Eye corrosion	-	0.9598	95.98%
Eye irritation	-	0.8569	85.69%
Skin irritation	-	0.8030	80.30%
Skin corrosion	-	0.8652	86.52%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6797	67.97%
Micronuclear	+	0.7833	78.33%
Hepatotoxicity	-	0.7071	70.71%
skin sensitisation	-	0.8284	82.84%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9260	92.60%
Acute Oral Toxicity (c)	III	0.6250	62.50%
Estrogen receptor binding	+	0.7065	70.65%
Androgen receptor binding	+	0.7166	71.66%
Thyroid receptor binding	+	0.5363	53.63%
Glucocorticoid receptor binding	+	0.7394	73.94%
Aromatase binding	-	0.6249	62.49%
PPAR gamma	+	0.5255	52.55%
Honey bee toxicity	-	0.8602	86.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9908	99.08%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	98.71%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.91%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.74%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.18%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.20%	95.56%
CHEMBL2581	P07339	Cathepsin D	93.91%	98.95%
CHEMBL4040	P28482	MAP kinase ERK2	92.70%	83.82%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.77%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.24%	89.62%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.70%	86.92%
CHEMBL1255126	O15151	Protein Mdm4	84.17%	90.20%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.53%	99.17%

Plants that contains it

• Arabidopsis thaliana

Cross-Links

• PubChem: 121232653
• LOTUS: LTS0125989
• wikiData: Q27163124