3-O-Feruloylquinic acid

Details

• Internal ID: 8023a71a-012c-4463-a03e-cda03da2d3a8
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OC2CC(CC(C2O)O)(C(=O)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)O[C@@H]2C[C@@](C[C@H]([C@H]2O)O)(C(=O)O)O)O
• InChI: InChI=1S/C17H20O9/c1-25-12-6-9(2-4-10(12)18)3-5-14(20)26-13-8-17(24,16(22)23)7-11(19)15(13)21/h2-6,11,13,15,18-19,21,24H,7-8H2,1H3,(H,22,23)/b5-3+/t11-,13-,15-,17+/m1/s1
• InChI Key: RAGZUCNPTLULOL-KJJWLSQTSA-N
• Popularity: 8 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₇H₂₀O₉
• Molecular Weight: 368.30 g/mol
• Exact Mass: 368.11073221 g/mol
• Topological Polar Surface Area (TPSA): 154.00 Ų
• XlogP: -0.10
• Atomic LogP (AlogP): -0.34
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• 3-O-feruloyl-D-quinic acid
• 62929-69-5
• CHEBI:86388
• 3-Feruloylquinic acid
• 5-O-Feruloylquinic acid
• C02572
• (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
• 3-O-(E)-Feruloylquinic acid
• 5-O-(E)-Feruloylquinic Acid
• C17H20O9
• C17-H20-O9
• 1899-29-2
• 3-Ferulylquinic acid
• SureCN10307370
• CHEMBL3526659
• SCHEMBL10307370
• MolPort-001-740-183
• DTXSID201310632
• NCGC00385499-01
• NP-000031
• Q27159124
• (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxy-cyclohexanecarboxylic acid
• (1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid
• 1,4alpha,5alpha-Trihydroxy-3beta-(3-methoxy-4-hydroxycinnamoyloxy)cyclohexane-1beta-carboxylic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8842	88.42%
Caco-2	-	0.9041	90.41%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.6942	69.42%
OATP2B1 inhibitior	-	0.8567	85.67%
OATP1B1 inhibitior	+	0.9489	94.89%
OATP1B3 inhibitior	+	0.9532	95.32%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8338	83.38%
BSEP inhibitior	-	0.6483	64.83%
P-glycoprotein inhibitior	-	0.9192	91.92%
P-glycoprotein substrate	-	0.7254	72.54%
CYP3A4 substrate	+	0.5924	59.24%
CYP2C9 substrate	-	0.5945	59.45%
CYP2D6 substrate	-	0.8441	84.41%
CYP3A4 inhibition	-	0.8808	88.08%
CYP2C9 inhibition	-	0.8664	86.64%
CYP2C19 inhibition	-	0.8833	88.33%
CYP2D6 inhibition	-	0.9250	92.50%
CYP1A2 inhibition	-	0.7843	78.43%
CYP2C8 inhibition	+	0.5743	57.43%
CYP inhibitory promiscuity	-	0.9700	97.00%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9064	90.64%
Carcinogenicity (trinary)	Non-required	0.6291	62.91%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9358	93.58%
Skin irritation	-	0.6563	65.63%
Skin corrosion	-	0.8562	85.62%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5596	55.96%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.6644	66.44%
skin sensitisation	-	0.7514	75.14%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8886	88.86%
Acute Oral Toxicity (c)	III	0.6988	69.88%
Estrogen receptor binding	+	0.7117	71.17%
Androgen receptor binding	+	0.5766	57.66%
Thyroid receptor binding	+	0.5686	56.86%
Glucocorticoid receptor binding	+	0.7185	71.85%
Aromatase binding	+	0.5327	53.27%
PPAR gamma	-	0.6509	65.09%
Honey bee toxicity	-	0.8775	87.75%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5555	55.55%
Fish aquatic toxicity	+	0.9703	97.03%

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	99.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.47%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.39%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	95.27%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.76%	86.33%
CHEMBL3194	P02766	Transthyretin	91.27%	90.71%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.93%	89.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.47%	94.45%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	90.31%	94.08%
CHEMBL4208	P20618	Proteasome component C5	89.72%	90.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	87.10%	95.50%
CHEMBL2535	P11166	Glucose transporter	85.39%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.98%	92.94%
CHEMBL221	P23219	Cyclooxygenase-1	84.47%	90.17%
CHEMBL2179	P04062	Beta-glucocerebrosidase	83.96%	85.31%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.78%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	83.35%	91.19%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.01%	85.14%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.44%	89.62%

Plants that contains it

• Ageratina tinifolia
• Amelanchier sanguinea
• Astragalus arguricus
• Astragalus robustus
• Cichorium intybus
• Coffea arabica
• Coffea canephora
• Coptis chinensis
• Coptis deltoidea
• Coptis japonica
• Coptis teeta
• Cynara cardunculus
• Eleutherococcus senticosus
• Epimedium brevicornu
• Epimedium grandiflorum
• Epimedium koreanum
• Epimedium pubescens
• Epimedium sagittatum
• Epimedium sempervirens
• Epimedium wushanense
• Foeniculum vulgare
• Humulus lupulus
• Hypericum perforatum
• Lophatherum gracile
• Phellodendron amurense
• Phellodendron chinense
• Phyllostachys edulis
• Prunus armeniaca
• Prunus cerasus
• Ribes nigrum
• Saussurea involucrata
• Stemona japonica

Cross-Links

• PubChem: 9799386
• NPASS: NPC98356
• LOTUS: LTS0039027
• wikiData: Q27159124