(2R,3S)-2-[4-[(E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-hydroxyphenoxy]-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Details

• Internal ID: 83e81419-e8c4-4b8c-9601-a061f712ed25
• Taxonomy: Lignans, neolignans and related compounds
• IUPAC Name: (2R,3S)-2-[4-[(E)-3-[(1S)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-hydroxyphenoxy]-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)OC(C(C3=CC(=C(C=C3)O)O)O)C(=O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@@H](C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O[C@H]([C@H](C3=CC(=C(C=C3)O)O)O)C(=O)O)O)O)O
• InChI: InChI=1S/C27H24O13/c28-16-5-1-14(10-18(16)30)11-22(26(35)36)39-23(33)8-3-13-2-7-21(20(32)9-13)40-25(27(37)38)24(34)15-4-6-17(29)19(31)12-15/h1-10,12,22,24-25,28-32,34H,11H2,(H,35,36)(H,37,38)/b8-3+/t22-,24-,25+/m0/s1
• InChI Key: AZOCLKLJIKZOLF-SYSOHKAWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₃
• Molecular Weight: 556.50 g/mol
• Exact Mass: 556.12169082 g/mol
• Topological Polar Surface Area (TPSA): 232.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 2.03
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7147	71.47%
Caco-2	-	0.9029	90.29%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.6524	65.24%
OATP2B1 inhibitior	+	0.5714	57.14%
OATP1B1 inhibitior	+	0.9077	90.77%
OATP1B3 inhibitior	+	0.9475	94.75%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.7838	78.38%
BSEP inhibitior	-	0.6208	62.08%
P-glycoprotein inhibitior	+	0.6084	60.84%
P-glycoprotein substrate	-	0.6416	64.16%
CYP3A4 substrate	+	0.5571	55.71%
CYP2C9 substrate	+	0.6016	60.16%
CYP2D6 substrate	-	0.8354	83.54%
CYP3A4 inhibition	-	0.6892	68.92%
CYP2C9 inhibition	-	0.8801	88.01%
CYP2C19 inhibition	-	0.9365	93.65%
CYP2D6 inhibition	-	0.9199	91.99%
CYP1A2 inhibition	-	0.7444	74.44%
CYP2C8 inhibition	+	0.7087	70.87%
CYP inhibitory promiscuity	-	0.8125	81.25%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8741	87.41%
Carcinogenicity (trinary)	Non-required	0.6717	67.17%
Eye corrosion	-	0.9935	99.35%
Eye irritation	-	0.8245	82.45%
Skin irritation	-	0.7124	71.24%
Skin corrosion	-	0.9299	92.99%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6788	67.88%
Micronuclear	+	0.7259	72.59%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.5575	55.75%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.8843	88.43%
Acute Oral Toxicity (c)	III	0.7838	78.38%
Estrogen receptor binding	+	0.6066	60.66%
Androgen receptor binding	+	0.7218	72.18%
Thyroid receptor binding	+	0.5163	51.63%
Glucocorticoid receptor binding	+	0.5490	54.90%
Aromatase binding	-	0.5364	53.64%
PPAR gamma	+	0.5851	58.51%
Honey bee toxicity	-	0.7056	70.56%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6641	66.41%
Fish aquatic toxicity	+	0.9927	99.27%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.32%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.52%	94.45%
CHEMBL3194	P02766	Transthyretin	96.17%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.24%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.18%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.06%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.72%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.34%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.24%	99.17%
CHEMBL1255126	O15151	Protein Mdm4	93.01%	90.20%
CHEMBL4208	P20618	Proteasome component C5	89.87%	90.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.83%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.61%	95.50%
CHEMBL4040	P28482	MAP kinase ERK2	89.28%	83.82%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	88.61%	95.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.59%	99.15%
CHEMBL3492	P49721	Proteasome Macropain subunit	88.30%	90.24%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.09%	91.71%
CHEMBL221	P23219	Cyclooxygenase-1	84.01%	90.17%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.33%	94.62%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	82.12%	80.78%
CHEMBL2535	P11166	Glucose transporter	81.80%	98.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.55%	89.00%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	80.90%	96.09%

Plants that contains it

• Salvia officinalis

Cross-Links

• PubChem: 163190096
• LOTUS: LTS0174384
• wikiData: Q104921824