[(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S)-4-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] benzoate

Details

• Internal ID: 9b65b120-e622-428c-a085-69ddc28ebefc
• Taxonomy: Phenylpropanoids and polyketides > Cinnamic acids and derivatives > Hydroxycinnamic acids and derivatives > Coumaric acids and derivatives
• IUPAC Name: [(2S,3R,4S,5S,6R)-6-[[(2R,3R,4S)-4-[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl] benzoate
• SMILES (Canonical): C1C(C(C(O1)OCC2C(C(C(C(O2)OC(=O)C3=CC=CC=C3)O)O)O)O)(COC(=O)C=CC4=CC(=C(C=C4)O)O)O
• SMILES (Isomeric): C1[C@@]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C3=CC=CC=C3)O)O)O)O)(COC(=O)/C=C/C4=CC(=C(C=C4)O)O)O
• InChI: InChI=1S/C27H30O14/c28-16-8-6-14(10-17(16)29)7-9-19(30)38-12-27(36)13-39-26(23(27)34)37-11-18-20(31)21(32)22(33)25(40-18)41-24(35)15-4-2-1-3-5-15/h1-10,18,20-23,25-26,28-29,31-34,36H,11-13H2/b9-7+/t18-,20-,21+,22-,23+,25+,26-,27-/m1/s1
• InChI Key: XKKMAZGQXTUOCG-OFSBUFHJSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₃₀O₁₄
• Molecular Weight: 578.50 g/mol
• Exact Mass: 578.16355563 g/mol
• Topological Polar Surface Area (TPSA): 222.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.22
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5993	59.93%
Caco-2	-	0.9037	90.37%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7112	71.12%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.8866	88.66%
OATP1B3 inhibitior	+	0.9357	93.57%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7634	76.34%
P-glycoprotein inhibitior	-	0.5216	52.16%
P-glycoprotein substrate	-	0.6560	65.60%
CYP3A4 substrate	+	0.6520	65.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8662	86.62%
CYP3A4 inhibition	-	0.8532	85.32%
CYP2C9 inhibition	-	0.8587	85.87%
CYP2C19 inhibition	-	0.8162	81.62%
CYP2D6 inhibition	-	0.9009	90.09%
CYP1A2 inhibition	-	0.9047	90.47%
CYP2C8 inhibition	+	0.8375	83.75%
CYP inhibitory promiscuity	-	0.8745	87.45%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5921	59.21%
Eye corrosion	-	0.9918	99.18%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.8326	83.26%
Skin corrosion	-	0.9443	94.43%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5281	52.81%
Micronuclear	-	0.5052	50.52%
Hepatotoxicity	-	0.6625	66.25%
skin sensitisation	-	0.7857	78.57%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9333	93.33%
Acute Oral Toxicity (c)	III	0.6373	63.73%
Estrogen receptor binding	+	0.7970	79.70%
Androgen receptor binding	+	0.6457	64.57%
Thyroid receptor binding	+	0.5381	53.81%
Glucocorticoid receptor binding	+	0.5803	58.03%
Aromatase binding	+	0.6832	68.32%
PPAR gamma	+	0.7054	70.54%
Honey bee toxicity	-	0.7779	77.79%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9632	96.32%

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	99.79%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	99.12%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.81%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.47%	94.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.45%	89.00%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	94.12%	94.23%
CHEMBL221	P23219	Cyclooxygenase-1	93.46%	90.17%
CHEMBL3475	P05121	Plasminogen activator inhibitor-1	93.32%	83.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.71%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.05%	96.00%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	90.23%	80.78%
CHEMBL2179	P04062	Beta-glucocerebrosidase	89.49%	85.31%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.42%	97.09%
CHEMBL2581	P07339	Cathepsin D	86.77%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.08%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	85.65%	94.08%
CHEMBL3194	P02766	Transthyretin	83.89%	90.71%
CHEMBL226	P30542	Adenosine A1 receptor	83.68%	95.93%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.66%	96.09%
CHEMBL3401	O75469	Pregnane X receptor	83.53%	94.73%
CHEMBL2535	P11166	Glucose transporter	82.64%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.56%	99.17%
CHEMBL5028	O14672	ADAM10	82.13%	97.50%
CHEMBL4208	P20618	Proteasome component C5	80.56%	90.00%

Plants that contains it

• Psydrax lividus

Cross-Links

• PubChem: 101924037
• LOTUS: LTS0236550
• wikiData: Q105329527