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

Details

• Internal ID: a87a4d78-32ae-4cde-939f-151d972cadcb
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Pentacarboxylic acids and derivatives
• IUPAC Name: (1S,3R,4R,5R)-4-(3-carboxypropanoyloxy)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-5-hydroxycyclohexane-1-carboxylic acid
• SMILES (Canonical): C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)OC(=O)CCC(=O)O)O
• SMILES (Isomeric): C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)OC(=O)CCC(=O)O)O
• InChI: InChI=1S/C29H28O15/c30-17-5-1-15(11-19(17)32)3-8-24(37)42-22-14-29(28(40)41,13-21(34)27(22)43-25(38)10-7-23(35)36)44-26(39)9-4-16-2-6-18(31)20(33)12-16/h1-6,8-9,11-12,21-22,27,30-34H,7,10,13-14H2,(H,35,36)(H,40,41)/b8-3+,9-4+/t21-,22-,27-,29+/m1/s1
• InChI Key: KMMYGGBDWQYIPW-WDDIIZOCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₂₈O₁₅
• Molecular Weight: 616.50 g/mol
• Exact Mass: 616.14282018 g/mol
• Topological Polar Surface Area (TPSA): 255.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 1.45
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8904	89.04%
Caco-2	-	0.9099	90.99%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8687	86.87%
OATP2B1 inhibitior	-	0.7094	70.94%
OATP1B1 inhibitior	+	0.8944	89.44%
OATP1B3 inhibitior	+	0.9404	94.04%
MATE1 inhibitior	-	0.7000	70.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8155	81.55%
P-glycoprotein inhibitior	+	0.7297	72.97%
P-glycoprotein substrate	-	0.6352	63.52%
CYP3A4 substrate	+	0.5877	58.77%
CYP2C9 substrate	-	0.6017	60.17%
CYP2D6 substrate	-	0.8542	85.42%
CYP3A4 inhibition	-	0.8574	85.74%
CYP2C9 inhibition	-	0.8590	85.90%
CYP2C19 inhibition	-	0.7988	79.88%
CYP2D6 inhibition	-	0.9470	94.70%
CYP1A2 inhibition	-	0.8080	80.80%
CYP2C8 inhibition	+	0.4743	47.43%
CYP inhibitory promiscuity	-	0.9696	96.96%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8543	85.43%
Carcinogenicity (trinary)	Non-required	0.6202	62.02%
Eye corrosion	-	0.9924	99.24%
Eye irritation	-	0.9091	90.91%
Skin irritation	-	0.7387	73.87%
Skin corrosion	-	0.9089	90.89%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6871	68.71%
Micronuclear	-	0.6441	64.41%
Hepatotoxicity	-	0.5875	58.75%
skin sensitisation	-	0.7369	73.69%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.9433	94.33%
Acute Oral Toxicity (c)	III	0.7566	75.66%
Estrogen receptor binding	+	0.7774	77.74%
Androgen receptor binding	+	0.7740	77.40%
Thyroid receptor binding	+	0.5212	52.12%
Glucocorticoid receptor binding	+	0.5758	57.58%
Aromatase binding	-	0.5313	53.13%
PPAR gamma	+	0.6225	62.25%
Honey bee toxicity	-	0.8309	83.09%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7455	74.55%
Fish aquatic toxicity	+	0.9907	99.07%

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	99.74%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	98.38%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.59%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	97.38%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.62%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.53%	94.45%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.07%	99.15%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.83%	96.00%
CHEMBL4208	P20618	Proteasome component C5	92.49%	90.00%
CHEMBL4040	P28482	MAP kinase ERK2	89.50%	83.82%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.17%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.42%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.15%	97.09%
CHEMBL3194	P02766	Transthyretin	85.49%	90.71%
CHEMBL340	P08684	Cytochrome P450 3A4	85.09%	91.19%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.96%	91.07%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	84.72%	94.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.39%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	83.07%	95.50%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	82.40%	94.08%
CHEMBL2581	P07339	Cathepsin D	82.38%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	82.13%	95.93%

Plants that contains it

• Arctium lappa

Cross-Links

• PubChem: 10145680
• LOTUS: LTS0140840
• wikiData: Q105143046