Cosalane
Basic information
- CAS
154212-56-3- Standard SMILES
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC[C@H]4C[C@@H](CCC=C(c5cc(Cl)c(O)c(C(=O)O)c5)c5cc(Cl)c(O)c(C(=O)O)c5)CC[C@]4(C)[C@H]3CC[C@]12C- InChIKey
VOJOOGPALCATLT-ZFQBPCNVSA-N- Molecular formula
- C45H60Cl2O6
- Average molar mass
- 767.9 g/mol
- Monoisotopic mass
- 766.376695
Overview
active against a variety of HIV-1 strains & against HIV-2; inhibits the binding of gp120 to CD4 cells & of the postbinding events that lead to fusion of the virus with the cell membrane
Names & identifiers
- Preferred name
- Cosalane
- IUPAC
- 5-[1-(3-carboxy-5-chloro-4-hydroxyphenyl)-4-[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]but-1-enyl]-3-chloro-2-hydroxybenzoic acid
- English name
- cosalane
- Molecular formula
- C45H60Cl2O6
- Molecular weight
- 767.86
Names & synonyms
Cosalane154212-56-3NSC-6585862R84Y6217JDTXSID00165567Benzoic acid, 3,3'-(4-(3beta,5alpha)-cholestan-3-yl-1-butenylidene)bis(5-chloro-6-hydroxy-NSC 658586RefChem:128187DTXCID4088058Benzoic acid, 3,3'-(4-((3beta,5alpha)-cholestan-3-yl)-1-buten-1-ylidene)bis(5-chloro-6-hydroxy)-5-[1-(3-carboxy-5-chloro-4-hydroxyphenyl)-4-[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl]but-1-enyl]-3-chloro-2-hydroxybenzoic acidNSC658586
Show more names
Benzoic acid, 3,3'-[4-(3β,5α)-cholestan-3-yl-1-butenylidene]bis[5-chloro-6-hydroxy-5-{4-[(1R,3aS,3bR,5aS,7S,9aS,9bS,11aR)-9a,11a-dimethyl-1-[(2R)-6-methylheptan-2-yl]-hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]-1-(3-carboxy-5-chloro-4-hydroxyphenyl)but-1-en-1-yl}-3-chloro-2-hydroxybenzoic acid
UNII-2R84Y6217JBENZOIC ACID, 3,3'-(4-(3.BETA.,5.ALPHA.)-CHOLESTAN-3-YL-1-BUTENYLIDENE)BIS(5-CHLORO-6-HYDROXY-Benzoic acid, 3,3'-[4-(3.beta.,5.alpha.)-cholestan-3-yl-1-butenylidene]bis[5-chloro-6-hydroxy-NSC640067orb1703582CHEMBL3545883SCHEMBL29374659GLXC-15174
Properties
Computed structural properties
- XLogP
- 16.5
- Topological polar surface area
- 115 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 12
- Heavy atoms
- 53
- Formal charge
- 0
- Complexity
- 1,280
Experimental & physicochemical properties
LogP6.94
Physicochemical properties
- Boiling point
- 797.4 · 797.4±60.0 °C(Predicted)
- Density
- 1.191 · 1.191±0.06 g/cm3(Predicted)
- pka
- 2.07 · 2.07±0.14(Predicted)
- form
- Solid
- color
- White to off-white
- Water Solubility
- 1.4 ug/L · 1.4ug/L(temperature not stated)
- FDA UNII
- 2 R84Y6217J · 2R84Y6217J
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAgents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS.
Applications
UsesCosalane (NSC 658586) is a potent inhibitor of HIV replication. Cosalane has an intrinsic ability to block human and murine CCR7 function in vitro in response to both of its natural ligands, CCL19 and CCL21, with the IC50 of 0.207/2.66 μM in human for CCL19/CCL21 and 0.193/1.98 μM in murine, respectively[1][2].
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