(1S,3R,4R,5S)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid

Details

• Internal ID: 209d3422-e87d-49ae-90a7-a7e109f3ba44
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (1S,3R,4R,5S)-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-/m0/s1
• InChI Key: CWVRJTMFETXNAD-JURSRTDWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

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

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

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

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

• Ageratina tomentella
• Asimina triloba
• Caralluma stalagmifera
• Centella asiatica
• Cephalaria gigantea
• Drymaria cordata
• Echinacea angustifolia
• Echinacea pallida
• Euthamia graminifolia
• Ficus nervosa
• Forsythia europaea
• Hedlundia thuringiaca
• Lasthenia californica subsp. californica
• Petasites japonicus
• Prosopis cineraria
• Rubus xanthocarpus
• Smallanthus sonchifolius
• Solanum melongena
• Sorbaria sorbifolia
• Sorbus tianschanica
• Uncaria hirsuta
• Valeriana amurensis
• Valeriana prionophylla
• Vincetoxicum hirundinaria subsp. hirundinaria

Cross-Links

• PubChem: 7067333
• NPASS: NPC208699
• LOTUS: LTS0221219
• wikiData: Q104971606