7-[(4S)-3-[(3R)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxoimidazolidin-4-yl]heptanoic acid

• ChemBase ID: 155766
• Molecular Formular: C19H32N2O5
• Molecular Mass: 368.46778
• Monoisotopic Mass: 368.23112213
• SMILES: C1CCC(CC1)[C@@H](CCN1[C@H](C(=O)NC1=O)CCCCCCC(=O)O)O
• Canonical SMILES: OC(=O)CCCCCC[C@H]1C(=O)NC(=O)N1CC[C@H](C1CCCCC1)O
• InChI: InChI=1S/C19H32N2O5/c22-16(14-8-4-3-5-9-14)12-13-21-15(18(25)20-19(21)26)10-6-1-2-7-11-17(23)24/h14-16,22H,1-13H2,(H,23,24)(H,20,25,26)/t15-,16+/m0/s1
• InChIKey: ZIDQIOZJEJFMOH-JKSUJKDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(4S)-3-[(3R)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxoimidazolidin-4-yl]heptanoic acid
• IUPAC Traditional name: 7-[(4S)-3-[(3R)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxoimidazolidin-4-yl]heptanoic acid
• Synonyms: 3-(3-Cyclohexyl-3-hydroxypropyl)-2,5-dioxo-(R*,S*)-(±)-4-imidazolineheptanioc acid; BW 245C

Database IDs

• CAS Number: 72814-32-5
• PubChem SID: 162249904; 24278046
• PubChem CID: 3080928

CALCULATED PROPERTIES

• Acid pKa: 4.3012652
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.0878845
• LogD (pH = 7.4): -0.65150934
• Log P: 2.3112519
• Molar Refractivity: 96.204 cm^3
• Polarizability: 37.886772 Å^3
• Polar Surface Area: 106.94 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble10 mg/mL
• Apperance: off-white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PTGDR(5729)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C19H32N2O5

DETAILS

Sigma Aldrich - B9305

Biochem/physiol Actions
BW 245C was investigated for the affinities potencies, and intrinsic activities in comparison with other natural and synthetic prostanoids using endogenous receptors. The rank order of compound affinities at the DP receptor was SQ27986 (K(i) = 10 +/- 2 nM) > RS93520 = ZK110841 = BW245C (K(i) = 23-26 nM) > ZK118182 (K(i) = 50 +/- 9 nM) > PGD(2) (K(i) = 80 +/- 5 nM). DP receptor agonists produced cAMP in embryonic bovine tracheal fibroblasts with different potencies (EC(50) values in nM): ZK118182 (18 +/- 6), RS93520 (28 +/- 6), SQ27986 (29 +/- 7), ZK110841 (31 +/- 7), BW245C (53 +/- 16), and PGD(2) (98 +/- 10). BW245C was more efficacious and RS93520 was less efficacious.