(2S,3S)-6-[(E)-3-[(1R)-1-carboxy-2-(4-hydroxy-3-methoxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxine-3-carboxylic acid

Details

• Internal ID: 93068e58-bdeb-45b8-902b-51810dbf15d1
• Taxonomy: Organoheterocyclic compounds > Benzodioxanes > Phenylbenzodioxanes > Phenylbenzo-1,4-dioxanes
• IUPAC Name: (2S,3S)-6-[(E)-3-[(1R)-1-carboxy-2-(4-hydroxy-3-methoxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-1,4-benzodioxine-3-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)CC(C(=O)O)OC(=O)C=CC2=CC3=C(C=C2)OC(C(O3)C(=O)O)C4=CC(=C(C=C4)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)C[C@H](C(=O)O)OC(=O)/C=C/C2=CC3=C(C=C2)O[C@H]([C@H](O3)C(=O)O)C4=CC(=C(C=C4)O)O)O
• InChI: InChI=1S/C28H24O12/c1-37-21-11-15(2-6-18(21)30)12-23(27(33)34)38-24(32)9-4-14-3-8-20-22(10-14)40-26(28(35)36)25(39-20)16-5-7-17(29)19(31)13-16/h2-11,13,23,25-26,29-31H,12H2,1H3,(H,33,34)(H,35,36)/b9-4+/t23-,25+,26+/m1/s1
• InChI Key: WBCYJTQLKQPOTQ-POMPZJGKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₂₄O₁₂
• Molecular Weight: 552.50 g/mol
• Exact Mass: 552.12677620 g/mol
• Topological Polar Surface Area (TPSA): 189.00 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.03
• H-Bond Acceptor: 10
• H-Bond Donor: 5
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8935	89.35%
Caco-2	-	0.9007	90.07%
Blood Brain Barrier	-	0.8250	82.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7209	72.09%
OATP2B1 inhibitior	-	0.8512	85.12%
OATP1B1 inhibitior	+	0.8805	88.05%
OATP1B3 inhibitior	+	0.9711	97.11%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7265	72.65%
P-glycoprotein inhibitior	+	0.6806	68.06%
P-glycoprotein substrate	-	0.6660	66.60%
CYP3A4 substrate	+	0.6371	63.71%
CYP2C9 substrate	-	0.6120	61.20%
CYP2D6 substrate	-	0.8314	83.14%
CYP3A4 inhibition	-	0.9059	90.59%
CYP2C9 inhibition	-	0.5663	56.63%
CYP2C19 inhibition	-	0.6473	64.73%
CYP2D6 inhibition	-	0.9388	93.88%
CYP1A2 inhibition	-	0.8766	87.66%
CYP2C8 inhibition	+	0.8565	85.65%
CYP inhibitory promiscuity	-	0.7943	79.43%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.4741	47.41%
Eye corrosion	-	0.9866	98.66%
Eye irritation	-	0.8821	88.21%
Skin irritation	-	0.7674	76.74%
Skin corrosion	-	0.9405	94.05%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4013	40.13%
Micronuclear	+	0.8418	84.18%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8881	88.81%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.9565	95.65%
Acute Oral Toxicity (c)	III	0.4938	49.38%
Estrogen receptor binding	+	0.7019	70.19%
Androgen receptor binding	+	0.7132	71.32%
Thyroid receptor binding	+	0.5622	56.22%
Glucocorticoid receptor binding	+	0.7205	72.05%
Aromatase binding	-	0.6661	66.61%
PPAR gamma	+	0.5454	54.54%
Honey bee toxicity	-	0.7225	72.25%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9554	95.54%

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	99.26%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.58%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.73%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	96.49%	99.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.12%	96.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	94.87%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.28%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.76%	85.14%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	93.46%	95.17%
CHEMBL2581	P07339	Cathepsin D	91.56%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.14%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.30%	89.00%
CHEMBL4040	P28482	MAP kinase ERK2	87.14%	83.82%
CHEMBL2413	P32246	C-C chemokine receptor type 1	86.51%	89.50%
CHEMBL3194	P02766	Transthyretin	84.31%	90.71%
CHEMBL2535	P11166	Glucose transporter	83.28%	98.75%
CHEMBL1255126	O15151	Protein Mdm4	83.19%	90.20%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.44%	92.62%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.09%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.54%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.09%	95.89%

Plants that contains it

• Clinopodium chinense

Cross-Links

• PubChem: 44254693
• LOTUS: LTS0193836
• wikiData: Q105300656