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[(3R)-1-[[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-3,4-dihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-(phosphonooxymethyl)oxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-phosphonooxyoxan-3-yl]amino]-1-oxotetradecan-3-yl] dodecanoate

HCID 56841121
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Basic information

CAS
171092-39-0
Standard SMILES
CCCCCCCCCCCC(=O)O[C@H](CCCCCCCCCCC)CC(=O)N[C@H]1[C@H](OC[C@H]2O[C@@H](COP(=O)(O)O)[C@H](NC(=O)C[C@H](O)CCCCCCCCCCC)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](OP(=O)(O)O)[C@@H]1O
InChIKey
UUVVKHSZRKZOGM-CUECXTGJSA-N
Molecular formula
C53H102N2O20P2
Average molar mass
1,149.3 g/mol
Monoisotopic mass
1,148.65011764

Overview

Defoslimod is a small molecule drug. The usage of the INN stem '-imod' in the name indicates that Defoslimod is a immunomodulator, both stimulant/suppressive and stimulant. Defoslimod is under investigation in clinical trial NCT01800812 (Effects of OM-174 in Adult Patients With Solid Tumors). Defoslimod has a monoisotopic molecular weight of 1148.65 Da.

Names & identifiers

Preferred name
[(3R)-1-[[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-3,4-dihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-(phosphonooxymethyl)oxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-phosphonooxyoxan-3-yl]amino]-1-oxotetradecan-3-yl] dodecanoate
IUPAC
[(3R)-1-[[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-3,4-dihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-(phosphonooxymethyl)oxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-phosphonooxyoxan-3-yl]amino]-1-oxotetradecan-3-yl] dodecanoate
English name
DEFOSLIMOD
Molecular formula
C52H100N2O20P2
Molecular weight
1135.3

Names & synonyms

Defoslimod [INN][(3R)-1-[[(2R,3R,4R,5S,6R)-2-[[(2R,3S,4R,5R,6R)-3,4-dihydroxy-5-[[(3R)-3-hydroxytetradecanoyl]amino]-6-(phosphonooxymethyl)oxan-2-yl]methoxy]-4-hydroxy-6-(hydroxymethyl)-5-phosphonooxyoxan-3-yl]amino]-1-oxotetradecan-3-yl] dodecanoateUNII-HC3530GGGGOM 174 lipid.ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-6-O-(2-DEOXY-2-(((3R)-1-OXO-3-((1-OXODODECYL)OXY)TETRADECYL)AMINO)-4-O-PHOSPHONO-.BETA.-D-GLUCOPYRANOSYL)-2-(((3R)-3-HYDROXY-1-OXOTETRADECYL)AMINO)-, 1-(DIHYDROGEN PHOSPHATE).ALPHA.-D-GLUCOPYRANOSE, 2-DEOXY-6-O-(2-DEOXY-2-((1-OXO-3-((1-OXODODECYL)OXY)TETRADECYL)AMINO)-4-O-PHOSPHONO-.BETA.-D-GLUCOPYRANOSYL)-2-((3-HYDROXY-1-OXOTETRADECYL)AMINO)-, 1-(DIHYDROGEN PHOSPHATE), (2(R),6(R))-2-DEOXY-6-O-(2-DEOXY-2-((R)-3-HYDROXYTETRADECANAMIDO)-.BETA.-D-GLUCOPYRANOSYL)-2-((R)-3-HYDROXYTETRADECANAMIDO)-.ALPHA.-D-GLUCOPYRANOSE 1,6'-BIS(DIHYDROGEN PHOSPHATE) 2'(3)-LAURATE2-Deoxy-6-O-(2-deoxy-2-((R)-3-hydroxytetradecanamido)-beta-D-glucopyranosyl)-2-((R)-3-hydroxytetradecanamido)-alpha-D-glucopyranose 1,6'-bis(dihydrogen phosphate) 2'(3)-laurate2-Deoxy-6-o-(2-deoxy-2-((R)-3-hydroxytetradecanamido)-beta-D-glucopyranosyl)-2-((R)-3-hydroxytetradecanamido)-alpha-D-glucopyranose 1,6'-bis(dihydrogen phosphate) 2'(3)-laurate.DEFOSLIMODα-D-Glucopyranose, 2-deoxy-6-O-[2-deoxy-2-[[(3R)-1-oxo-3-[(1-oxododecyl)oxy]tetradecyl]amino]-4-O-phosphono-β-D-glucopyranosyl]-2-[[(3R)-3-hydroxy-1-oxotetradecyl]amino]-, 1-(dihydrogen phosphate)

Database identifiers

CAS
171092-39-0
PubChem CID
56841121
UNII
HC3530GGGG

Properties

Computed structural properties

XLogP
8.5
Topological polar surface area
347 Ų
Hydrogen bond donors
11
Hydrogen bond acceptors
20
Rotatable bonds
47
Heavy atoms
77
Formal charge
0
Complexity
1,660

Physicochemical properties

Density
1.25 · 1.25±0.1 g/cm3(Predicted)
pka
1.73 · 1.73±0.10(Predicted)
FDA UNII
3530 GGGG · HC3530GGGG

Chemistry & industry

Applications

UsesDefoslimod (OM 174) is an agonist for TLR4 receptor and acts as an immunomodulator. Defoslimod activates macrophages and dendritic cells, induces cytokines secretion, and exhibits antitumor efficacy in rats[1].

Suppliers2 total

北京华美互利生物化工010-56205725 · [email protected]
陕西缔都医药有限责任公司81148925 17391631969 · [email protected]

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Compound notes

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