methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(2R,3S,4S,5R,6R)-6-[2-[4-[2-[(2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxyphenyl]ethoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate

Details

• Internal ID: b1d46242-b88f-4499-bfa7-1138f0b03a78
• Taxonomy: Lipids and lipid-like molecules > Saccharolipids
• IUPAC Name: methyl (4S,5E,6S)-5-ethylidene-4-[2-[[(2R,3S,4S,5R,6R)-6-[2-[4-[2-[(2S,3E,4S)-3-ethylidene-5-methoxycarbonyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-4-yl]acetyl]oxyphenyl]ethoxy]-3,4,5-trihydroxyoxan-2-yl]methoxy]-2-oxoethyl]-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate
• SMILES (Canonical): CC=C1C(C(=COC1OC2C(C(C(C(O2)CO)O)O)O)C(=O)OC)CC(=O)OCC3C(C(C(C(O3)OCCC4=CC=C(C=C4)OC(=O)CC5C(=COC(C5=CC)OC6C(C(C(C(O6)CO)O)O)O)C(=O)OC)O)O)O
• SMILES (Isomeric): C/C=C/1\[C@@H](C(=CO[C@H]1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)C(=O)OC)CC(=O)OC[C@@H]3[C@H]([C@@H]([C@H]([C@@H](O3)OCCC4=CC=C(C=C4)OC(=O)C[C@@H]\5C(=CO[C@H](/C5=C/C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C(=O)OC)O)O)O
• InChI: InChI=1S/C48H64O27/c1-5-22-24(26(42(62)64-3)17-68-44(22)74-47-40(60)36(56)33(53)28(15-49)71-47)13-31(51)67-19-30-35(55)38(58)39(59)46(73-30)66-12-11-20-7-9-21(10-8-20)70-32(52)14-25-23(6-2)45(69-18-27(25)43(63)65-4)75-48-41(61)37(57)34(54)29(16-50)72-48/h5-10,17-18,24-25,28-30,33-41,44-50,53-61H,11-16,19H2,1-4H3/b22-5+,23-6+/t24-,25-,28+,29+,30+,33+,34+,35+,36-,37-,38-,39+,40+,41+,44-,45-,46+,47-,48-/m0/s1
• InChI Key: SMSRUMQQXKEQCV-NKRYKJGSSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₆₄O₂₇
• Molecular Weight: 1073.00 g/mol
• Exact Mass: 1072.36349676 g/mol
• Topological Polar Surface Area (TPSA): 402.00 Ų
• XlogP: -3.90
• Atomic LogP (AlogP): -4.13
• H-Bond Acceptor: 27
• H-Bond Donor: 11
• Rotatable Bonds: 19

Synonyms

• GL3
• HY-N6873
• AKOS040760138
• MS-31923
• CS-0100455
• E80678

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7593	75.93%
Caco-2	-	0.8613	86.13%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7842	78.42%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7493	74.93%
OATP1B3 inhibitior	+	0.9177	91.77%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9804	98.04%
P-glycoprotein inhibitior	+	0.7444	74.44%
P-glycoprotein substrate	+	0.5670	56.70%
CYP3A4 substrate	+	0.6914	69.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8820	88.20%
CYP3A4 inhibition	-	0.7898	78.98%
CYP2C9 inhibition	-	0.8070	80.70%
CYP2C19 inhibition	-	0.7455	74.55%
CYP2D6 inhibition	-	0.8987	89.87%
CYP1A2 inhibition	-	0.8484	84.84%
CYP2C8 inhibition	+	0.7726	77.26%
CYP inhibitory promiscuity	-	0.8446	84.46%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6131	61.31%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.8996	89.96%
Skin irritation	-	0.8085	80.85%
Skin corrosion	-	0.9561	95.61%
Ames mutagenesis	-	0.5000	50.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7896	78.96%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	-	0.7966	79.66%
skin sensitisation	-	0.8596	85.96%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6274	62.74%
Acute Oral Toxicity (c)	III	0.6659	66.59%
Estrogen receptor binding	+	0.8187	81.87%
Androgen receptor binding	+	0.7166	71.66%
Thyroid receptor binding	+	0.6207	62.07%
Glucocorticoid receptor binding	+	0.7646	76.46%
Aromatase binding	+	0.5993	59.93%
PPAR gamma	+	0.8210	82.10%
Honey bee toxicity	-	0.6532	65.32%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.8322	83.22%

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%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	96.07%	86.92%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.39%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.07%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.71%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	92.04%	94.73%
CHEMBL3437	Q16853	Amine oxidase, copper containing	90.89%	94.00%
CHEMBL2581	P07339	Cathepsin D	90.34%	98.95%
CHEMBL2243	O00519	Anandamide amidohydrolase	90.01%	97.53%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.73%	96.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.81%	94.45%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.10%	94.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.12%	95.89%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	83.36%	95.83%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.74%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.82%	94.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	81.81%	95.17%

Plants that contains it

• Fraxinus excelsior
• Ligustrum lucidum

Cross-Links

• PubChem: 102196658
• LOTUS: LTS0090206
• wikiData: Q105256156