Ligustrosidic acid

Details

• Internal ID: 55311098-bec5-4615-9a96-360018a07072
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides
• IUPAC Name: (2E)-2-[4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-ylidene]acetic acid
• SMILES (Canonical): COC(=O)C1=COC(C(=CC(=O)O)C1CC(=O)OCCC2=CC=C(C=C2)O)OC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC(=O)C1=COC(/C(=C/C(=O)O)/C1CC(=O)OCCC2=CC=C(C=C2)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C25H30O14/c1-35-23(34)16-11-37-24(39-25-22(33)21(32)20(31)17(10-26)38-25)15(8-18(28)29)14(16)9-19(30)36-7-6-12-2-4-13(27)5-3-12/h2-5,8,11,14,17,20-22,24-27,31-33H,6-7,9-10H2,1H3,(H,28,29)/b15-8+/t14?,17-,20-,21+,22-,24?,25+/m1/s1
• InChI Key: DJAAGTPILCOZIR-MSISIIAVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₀O₁₄
• Molecular Weight: 554.50 g/mol
• Exact Mass: 554.16355563 g/mol
• Topological Polar Surface Area (TPSA): 219.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.28
• H-Bond Acceptor: 13
• H-Bond Donor: 6
• Rotatable Bonds: 10

Synonyms

• 96382-89-7
• (2E)-2-[4-[2-[2-(4-hydroxyphenyl)ethoxy]-2-oxoethyl]-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-ylidene]acetic acid
• HY-N6874
• MS-30115
• CS-0100461
• F82430

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7129	71.29%
Caco-2	-	0.9105	91.05%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8423	84.23%
OATP2B1 inhibitior	-	0.8563	85.63%
OATP1B1 inhibitior	+	0.7363	73.63%
OATP1B3 inhibitior	+	0.9471	94.71%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.6623	66.23%
P-glycoprotein inhibitior	-	0.5000	50.00%
P-glycoprotein substrate	+	0.5192	51.92%
CYP3A4 substrate	+	0.6753	67.53%
CYP2C9 substrate	-	0.6134	61.34%
CYP2D6 substrate	-	0.8780	87.80%
CYP3A4 inhibition	-	0.9304	93.04%
CYP2C9 inhibition	-	0.8577	85.77%
CYP2C19 inhibition	-	0.7491	74.91%
CYP2D6 inhibition	-	0.8903	89.03%
CYP1A2 inhibition	-	0.8160	81.60%
CYP2C8 inhibition	+	0.8254	82.54%
CYP inhibitory promiscuity	-	0.8875	88.75%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6610	66.10%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9186	91.86%
Skin irritation	-	0.8275	82.75%
Skin corrosion	-	0.9615	96.15%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4316	43.16%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8125	81.25%
skin sensitisation	-	0.8610	86.10%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6441	64.41%
Acute Oral Toxicity (c)	III	0.6226	62.26%
Estrogen receptor binding	+	0.8366	83.66%
Androgen receptor binding	+	0.6775	67.75%
Thyroid receptor binding	-	0.5274	52.74%
Glucocorticoid receptor binding	+	0.6796	67.96%
Aromatase binding	-	0.5768	57.68%
PPAR gamma	+	0.6560	65.60%
Honey bee toxicity	-	0.6683	66.83%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6700	67.00%
Fish aquatic toxicity	+	0.8700	87.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.16%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.72%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.41%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.62%	86.33%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	91.09%	95.64%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.93%	94.62%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.80%	94.45%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	89.97%	86.92%
CHEMBL2581	P07339	Cathepsin D	89.96%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	88.45%	94.73%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.83%	95.89%
CHEMBL3891	P07384	Calpain 1	82.16%	93.04%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.92%	95.89%
CHEMBL3437	Q16853	Amine oxidase, copper containing	80.86%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.84%	94.33%
CHEMBL2996	Q05655	Protein kinase C delta	80.77%	97.79%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.74%	96.90%

Plants that contains it

• Ligustrum lucidum

Cross-Links

• PubChem: 146014676
• LOTUS: LTS0164211
• wikiData: Q104981871