(S)-2-((R)-3-(decanoyloxy)tetradecanamido)-3-((2R,3R,4R,5S,6R)-3-((R)-3-(decanoyloxy)tetradecanamido)-4-((R)-3-(decanoyloxy)tetradecanoyloxy)-6-(hydroxymethyl)-5-(phosphonooxy)tetrahydro-2H-pyran-2-yloxy)propanoic acid

ID: ALA448191

Chembl Id: CHEMBL448191

PubChem CID: 9877226

Max Phase: Preclinical

Molecular Formula: C81H151N2O19P

Molecular Weight: 1488.07

Molecule Type: Small molecule

Names and Identifiers

Synonyms: CRX-527 | CHEMBL448191|SCHEMBL7128242|CRX-527|N-[(3R)-3-(Decanoyloxy)myristoyl]-O-[2-[[(3R)-3-(decanoyloxy)myristoyl]amino]-3-O-[(3R)-3-(decanoyloxy)myristoyl]-4-O-phosphono-2-deoxy-beta-D-glucopyranosyl]-L-serine|(2S)-2-[[(3R)-3-decanoyloxytetradecanoyl]amino]-3-[(2R,3R,4R,5S,6R)-3-[[(3R)-3-decanoyloxytetradecanoyl]amino]-4-[(3R)-3-decanoyloxytetradecanoyl]oxy-6-(hydroxymethyl)-5-phosphonooxyoxan-2-yl]oxypropanoic acid

Canonical SMILES:  CCCCCCCCCCC[C@H](CC(=O)N[C@H]1[C@H](OC[C@H](NC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCC)C(=O)O)O[C@H](CO)[C@@H](OP(=O)(O)O)[C@@H]1OC(=O)C[C@@H](CCCCCCCCCCC)OC(=O)CCCCCCCCC)OC(=O)CCCCCCCCC

Standard InChI:  InChI=1S/C81H151N2O19P/c1-7-13-19-25-31-34-40-43-49-55-66(97-73(87)58-52-46-37-28-22-16-10-4)61-71(85)82-69(80(91)92)65-96-81-77(83-72(86)62-67(56-50-44-41-35-32-26-20-14-8-2)98-74(88)59-53-47-38-29-23-17-11-5)79(78(70(64-84)100-81)102-103(93,94)95)101-76(90)63-68(57-51-45-42-36-33-27-21-15-9-3)99-75(89)60-54-48-39-30-24-18-12-6/h66-70,77-79,81,84H,7-65H2,1-6H3,(H,82,85)(H,83,86)(H,91,92)(H2,93,94,95)/t66-,67-,68-,69+,70-,77-,78-,79-,81-/m1/s1

Standard InChI Key:  REEGNIYAMZUTIO-MGSMBCBTSA-N

Alternative Forms

1. Parent:

   

   ALA448191

   N-[(3R)-3-(Decanoyloxy)myristoyl]-O-[2-[[(3R)-3-(decanoyloxy)myristoyl]amino]-3-O-[(3R)-3-(decanoyloxy)myristoyl]-4-O-phosphono-2-deoxy-beta-D-glucopyranosyl]-L-serine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 1488.07

Molecular Weight (Monoisotopic): 1487.0649

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References

1. Bazin HG, Murray TJ, Bowen WS, Mozaffarian A, Fling SP, Bess LS, Livesay MT, Arnold JS, Johnson CL, Ryter KT, Cluff CW, Evans JT, Johnson DA..  (2008)  The 'Ethereal' nature of TLR4 agonism and antagonism in the AGP class of lipid A mimetics.,  18  (20): [PMID:18835160] [10.1016/j.bmcl.2008.09.060]

2. Khalaf JK, Bowen WS, Bazin HG, Ryter KT, Livesay MT, Ward JR, Evans JT, Johnson DA..  (2015)  Characterization of TRIF selectivity in the AGP class of lipid A mimetics: role of secondary lipid chains.,  25  (3): [PMID:25553892] [10.1016/j.bmcl.2014.12.024]

3. Reintjens NRM,Tondini E,de Jong AR,Meeuwenoord NJ,Chiodo F,Peterse E,Overkleeft HS,Filippov DV,van der Marel GA,Ossendorp F,Codée JDC.  (2020)  Self-Adjuvanting Cancer Vaccines from Conjugation-Ready Lipid A Analogues and Synthetic Long Peptides.,  63  (20.0): [PMID:32960056] [10.1021/acs.jmedchem.0c00851]

Source

Source(1):

• Scientific Literature