3,5-di-O-caffeoyl-muco-quinic acid

Details

• Internal ID: 28feffb7-a059-47c6-a36b-fc62f9b5b6dc
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (3R,5S)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
• SMILES (Canonical): C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O
• SMILES (Isomeric): C1C(C[C@@H](C([C@@H]1OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(O)C(=O)O
• InChI: InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(30)36-19-11-25(35,24(33)34)12-20(23(19)32)37-22(31)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-29,32,35H,11-12H2,(H,33,34)/b7-3+,8-4+/t19-,20+,23?,25?
• InChI Key: KRZBCHWVBQOTNZ-WSSGNCIPSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₂₄O₁₂
• Molecular Weight: 516.40 g/mol
• Exact Mass: 516.12677620 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.03
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• (3R,5S)-3,5-bis{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4-dihydroxycyclohexanecarboxylic acid
• CHEBI:521393
• DTXSID701031209
• (-)3,5-Dicaffeoyl-muco-quinic acid
• (?)-3,5-Dicaffeoyl-muco-quinic acid
• Q27225765
• (3R,5S)-3,5-Bis-[(E)-3-(3,4-dihydroxy-phenyl)-allanoyloxy]-1,4-dihydroxy-cyclohexanecarboxylic acid
• (3R,5S)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxycyclohexane-1-carboxylic acid
• (3S,5R)-3,5-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-1,4-dihydroxy-cyclohexanecarboxylic acid
• 1,4alpha-Dihydroxy-3beta,5beta-bis(3,4-dihydroxy-trans-cinnamoyloxy)cyclohexane-1beta-carboxylic acid
• 1beta,4alpha-Dihydroxy-3alpha,5alpha-bis[[(2E)-3-(3,4-dihydroxyphenyl)propenoyl]oxy]cyclohexanecarboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9651	96.51%
Caco-2	-	0.9069	90.69%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.8118	81.18%
OATP2B1 inhibitior	-	0.7089	70.89%
OATP1B1 inhibitior	+	0.9692	96.92%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7868	78.68%
P-glycoprotein inhibitior	+	0.6229	62.29%
P-glycoprotein substrate	-	0.8808	88.08%
CYP3A4 substrate	+	0.5281	52.81%
CYP2C9 substrate	-	0.5941	59.41%
CYP2D6 substrate	-	0.8566	85.66%
CYP3A4 inhibition	-	0.9206	92.06%
CYP2C9 inhibition	-	0.9236	92.36%
CYP2C19 inhibition	-	0.8975	89.75%
CYP2D6 inhibition	-	0.9548	95.48%
CYP1A2 inhibition	-	0.8878	88.78%
CYP2C8 inhibition	+	0.4547	45.47%
CYP inhibitory promiscuity	-	0.9803	98.03%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8764	87.64%
Carcinogenicity (trinary)	Non-required	0.5620	56.20%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.8916	89.16%
Skin irritation	-	0.7018	70.18%
Skin corrosion	-	0.9182	91.82%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3888	38.88%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.7431	74.31%
skin sensitisation	-	0.5835	58.35%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.8184	81.84%
Acute Oral Toxicity (c)	III	0.7686	76.86%
Estrogen receptor binding	+	0.7607	76.07%
Androgen receptor binding	+	0.7363	73.63%
Thyroid receptor binding	+	0.5658	56.58%
Glucocorticoid receptor binding	+	0.6811	68.11%
Aromatase binding	-	0.5534	55.34%
PPAR gamma	+	0.6232	62.32%
Honey bee toxicity	-	0.8390	83.90%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9943	99.43%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5983	O60218	Aldo-keto reductase family 1 member B10	130 nM	IC50	via Super-PRED
CHEMBL1900	P15121	Aldose reductase	88 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.64%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	93.87%	91.49%
CHEMBL221	P23219	Cyclooxygenase-1	93.20%	90.17%
CHEMBL3194	P02766	Transthyretin	92.98%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.21%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.37%	94.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.74%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.65%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.15%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.15%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.90%	94.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.29%	94.45%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	88.14%	97.53%
CHEMBL4208	P20618	Proteasome component C5	86.85%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.21%	99.15%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.88%	94.23%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.11%	97.09%
CHEMBL2179	P04062	Beta-glucocerebrosidase	81.62%	85.31%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	80.93%	94.97%
CHEMBL340	P08684	Cytochrome P450 3A4	80.67%	91.19%

Plants that contains it

• Artemisia argyi
• Artemisia montana
• Artemisia princeps

Cross-Links

• PubChem: 6475855
• NPASS: NPC275954