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

Details

• Internal ID: d4d7018c-354e-40e1-9950-901890e48efa
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4-dihydroxy-5-[(E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid
• SMILES (Canonical): COC1=C(C=C(C=C1)C=CC(=O)OC2CC(CC(C2O)OC(=O)C=CC3=CC(=C(C=C3)O)O)(C(=O)O)O)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)/C=C/C(=O)O[C@@H]2C[C@@](C[C@H]([C@H]2O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)(C(=O)O)O)O
• InChI: InChI=1S/C26H26O12/c1-36-19-7-3-15(11-18(19)29)5-9-23(31)38-21-13-26(35,25(33)34)12-20(24(21)32)37-22(30)8-4-14-2-6-16(27)17(28)10-14/h2-11,20-21,24,27-29,32,35H,12-13H2,1H3,(H,33,34)/b8-4+,9-5+/t20-,21-,24-,26+/m1/s1
• InChI Key: MLWOGXLYVLMHAS-VOHNXBSUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₆O₁₂
• Molecular Weight: 530.50 g/mol
• Exact Mass: 530.14242626 g/mol
• Topological Polar Surface Area (TPSA): 200.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 11
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9725	97.25%
Caco-2	-	0.8845	88.45%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8147	81.47%
OATP2B1 inhibitior	-	0.7117	71.17%
OATP1B1 inhibitior	+	0.9549	95.49%
OATP1B3 inhibitior	+	0.9496	94.96%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.7365	73.65%
P-glycoprotein inhibitior	+	0.6361	63.61%
P-glycoprotein substrate	-	0.7224	72.24%
CYP3A4 substrate	+	0.5949	59.49%
CYP2C9 substrate	+	0.6014	60.14%
CYP2D6 substrate	-	0.8439	84.39%
CYP3A4 inhibition	-	0.9243	92.43%
CYP2C9 inhibition	-	0.9007	90.07%
CYP2C19 inhibition	-	0.8809	88.09%
CYP2D6 inhibition	-	0.9490	94.90%
CYP1A2 inhibition	-	0.7737	77.37%
CYP2C8 inhibition	+	0.6089	60.89%
CYP inhibitory promiscuity	-	0.9818	98.18%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8664	86.64%
Carcinogenicity (trinary)	Non-required	0.5959	59.59%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9205	92.05%
Skin irritation	-	0.7295	72.95%
Skin corrosion	-	0.8889	88.89%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7248	72.48%
Micronuclear	+	0.6000	60.00%
Hepatotoxicity	+	0.6931	69.31%
skin sensitisation	-	0.7834	78.34%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.8129	81.29%
Acute Oral Toxicity (c)	III	0.6689	66.89%
Estrogen receptor binding	+	0.8006	80.06%
Androgen receptor binding	+	0.6961	69.61%
Thyroid receptor binding	+	0.5656	56.56%
Glucocorticoid receptor binding	+	0.7249	72.49%
Aromatase binding	-	0.5054	50.54%
PPAR gamma	+	0.5390	53.90%
Honey bee toxicity	-	0.8489	84.89%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6655	66.55%
Fish aquatic toxicity	+	0.9887	98.87%

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	99.18%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.45%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.71%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.69%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.30%	96.00%
CHEMBL3194	P02766	Transthyretin	92.50%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	90.50%	91.49%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.20%	89.00%
CHEMBL4208	P20618	Proteasome component C5	89.38%	90.00%
CHEMBL221	P23219	Cyclooxygenase-1	89.06%	90.17%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.08%	94.45%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.63%	94.08%
CHEMBL2535	P11166	Glucose transporter	85.17%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.21%	95.89%
CHEMBL340	P08684	Cytochrome P450 3A4	84.14%	91.19%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.59%	95.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.57%	92.94%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.07%	91.03%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.64%	91.07%

Plants that contains it

• Helichrysum stoechas

Cross-Links

• PubChem: 163194138
• LOTUS: LTS0017148
• wikiData: Q105167256