Neochlorogenic acid

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	373f2dff-2265-4ddb-a77c-055ab20bc4c9
Taxonomy	Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
IUPAC Name	(1R,3R,4S,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
SMILES (Canonical)	C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
SMILES (Isomeric)	C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
InChI	InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14+,16-/m1/s1
InChI Key	CWVRJTMFETXNAD-NXLLHMKUSA-N
Popularity	99 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₆H₁₈O₉
Molecular Weight	354.31 g/mol
Exact Mass	354.09508215 g/mol
Topological Polar Surface Area (TPSA)	165.00 Å²
XlogP	-0.40
Atomic LogP (AlogP)	-0.65
H-Bond Acceptor	8
H-Bond Donor	6
Rotatable Bonds	4

Synonyms

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906-33-2

(E)-Neochlorogenic Acid

5-Caffeylquinic acid

UNII-O4601UER1Z

O4601UER1Z

EINECS 212-997-1

3-CQA

3-O-(E)-CAFFEOYLQUINIC ACID

Cyclohexanecarboxylic acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1R-(1alpha,3alpha,4alpha,5beta))-

CYCLOHEXANECARBOXYLIC ACID, 3-(((2E)-3-(3,4-DIHYDROXYPHENYL)-1-OXO-2-PROPEN-1-YL)OXY)-1,4,5-TRIHYDROXY-, (1R,3R,4S,5R)-

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8565	85.65%
Caco-2	-	0.9230	92.30%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6770	67.70%
OATP2B1 inhibitior	-	0.5784	57.84%
OATP1B1 inhibitior	+	0.9640	96.40%
OATP1B3 inhibitior	+	0.9473	94.73%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.8588	85.88%
BSEP inhibitior	-	0.7020	70.20%
P-glycoprotein inhibitior	-	0.9329	93.29%
P-glycoprotein substrate	-	0.8340	83.40%
CYP3A4 substrate	+	0.5526	55.26%
CYP2C9 substrate	+	0.6014	60.14%
CYP2D6 substrate	-	0.8568	85.68%
CYP3A4 inhibition	-	0.8744	87.44%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9069	90.69%
CYP2D6 inhibition	-	0.9388	93.88%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.4526	45.26%
CYP inhibitory promiscuity	-	0.9686	96.86%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9064	90.64%
Carcinogenicity (trinary)	Non-required	0.6128	61.28%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8986	89.86%
Skin irritation	-	0.6297	62.97%
Skin corrosion	-	0.8862	88.62%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5420	54.20%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	+	0.8750	87.50%
skin sensitisation	-	0.5785	57.85%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8806	88.06%
Acute Oral Toxicity (c)	III	0.7775	77.75%
Estrogen receptor binding	+	0.7776	77.76%
Androgen receptor binding	+	0.6557	65.57%
Thyroid receptor binding	-	0.5000	50.00%
Glucocorticoid receptor binding	+	0.7362	73.62%
Aromatase binding	+	0.6016	60.16%
PPAR gamma	+	0.5828	58.28%
Honey bee toxicity	-	0.8348	83.48%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9844	98.44%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1900	P15121	Aldose reductase	300 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	99.68%	91.11%
CHEMBL3194	P02766	Transthyretin	92.33%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.21%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	91.84%	94.62%
CHEMBL1951	P21397	Monoamine oxidase A	91.80%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.73%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.16%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.14%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	90.83%	90.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.63%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.33%	96.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	90.18%	97.53%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.66%	94.08%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	88.14%	94.23%
CHEMBL2179	P04062	Beta-glucocerebrosidase	87.78%	85.31%
CHEMBL4208	P20618	Proteasome component C5	87.47%	90.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.05%	99.15%
CHEMBL211	P08172	Muscarinic acetylcholine receptor M2	84.95%	94.97%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.72%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.57%	97.09%
CHEMBL340	P08684	Cytochrome P450 3A4	81.18%	91.19%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Acer truncatum

Acmella ciliata

Actiniopteris radiata