(1R,2R,3S,4R)-6-[(E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid

Details

• Internal ID: 98a811a6-558c-4203-ac83-0f770e45f1d2
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: (1R,2R,3S,4R)-6-[(E)-3-[(1R)-1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-3-(3,4-dihydroxyphenyl)cyclohex-5-ene-1,2,4-tricarboxylic acid
• SMILES (Canonical): C1=CC(=C(C=C1CC(C(=O)O)OC(=O)C=CC2=CC(C(C(C2C(=O)O)C(=O)O)C3=CC(=C(C=C3)O)O)C(=O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C[C@H](C(=O)O)OC(=O)/C=C/C2=C[C@H]([C@@H]([C@H]([C@H]2C(=O)O)C(=O)O)C3=CC(=C(C=C3)O)O)C(=O)O)O)O
• InChI: InChI=1S/C27H24O14/c28-15-4-1-11(7-17(15)30)8-19(25(35)36)41-20(32)6-3-12-9-14(24(33)34)21(13-2-5-16(29)18(31)10-13)23(27(39)40)22(12)26(37)38/h1-7,9-10,14,19,21-23,28-31H,8H2,(H,33,34)(H,35,36)(H,37,38)(H,39,40)/b6-3+/t14-,19-,21+,22+,23-/m1/s1
• InChI Key: JSOPGXFFNOKRAX-BWAFDSPASA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₄O₁₄
• Molecular Weight: 572.50 g/mol
• Exact Mass: 572.11660544 g/mol
• Topological Polar Surface Area (TPSA): 256.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.43
• H-Bond Acceptor: 10
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9320	93.20%
Caco-2	-	0.9355	93.55%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8545	85.45%
OATP2B1 inhibitior	-	0.5635	56.35%
OATP1B1 inhibitior	+	0.9022	90.22%
OATP1B3 inhibitior	+	0.9206	92.06%
MATE1 inhibitior	-	0.6200	62.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.6142	61.42%
P-glycoprotein substrate	-	0.6299	62.99%
CYP3A4 substrate	+	0.6166	61.66%
CYP2C9 substrate	-	0.5824	58.24%
CYP2D6 substrate	-	0.8681	86.81%
CYP3A4 inhibition	-	0.9257	92.57%
CYP2C9 inhibition	-	0.5715	57.15%
CYP2C19 inhibition	-	0.7931	79.31%
CYP2D6 inhibition	-	0.8857	88.57%
CYP1A2 inhibition	-	0.5132	51.32%
CYP2C8 inhibition	+	0.6316	63.16%
CYP inhibitory promiscuity	-	0.6270	62.70%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8020	80.20%
Carcinogenicity (trinary)	Non-required	0.6156	61.56%
Eye corrosion	-	0.9921	99.21%
Eye irritation	-	0.8666	86.66%
Skin irritation	-	0.7675	76.75%
Skin corrosion	-	0.9517	95.17%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4388	43.88%
Micronuclear	+	0.7518	75.18%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.5563	55.63%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7987	79.87%
Acute Oral Toxicity (c)	III	0.5955	59.55%
Estrogen receptor binding	+	0.6950	69.50%
Androgen receptor binding	+	0.7426	74.26%
Thyroid receptor binding	+	0.5306	53.06%
Glucocorticoid receptor binding	+	0.5494	54.94%
Aromatase binding	-	0.7048	70.48%
PPAR gamma	+	0.6110	61.10%
Honey bee toxicity	-	0.6448	64.48%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9973	99.73%

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	99.27%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.25%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.84%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.64%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	91.41%	96.95%
CHEMBL3194	P02766	Transthyretin	90.07%	90.71%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.88%	97.21%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	89.41%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.91%	99.17%
CHEMBL2581	P07339	Cathepsin D	87.99%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.94%	86.33%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.61%	91.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.86%	96.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.74%	97.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.01%	99.15%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.83%	95.89%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.02%	95.50%
CHEMBL340	P08684	Cytochrome P450 3A4	81.05%	91.19%
CHEMBL221	P23219	Cyclooxygenase-1	80.48%	90.17%
CHEMBL4040	P28482	MAP kinase ERK2	80.45%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.19%	95.56%

Plants that contains it

• Isodon rubescens
• Salvia miltiorrhiza
• Salvia yunnanensis

Cross-Links

• PubChem: 10531154
• NPASS: NPC140182
• LOTUS: LTS0192656
• wikiData: Q105134489