methyl 16-hydroxyhexadecanoate

• ChemBase ID: 153306
• Molecular Formular: C17H34O3
• Molecular Mass: 286.45006
• Monoisotopic Mass: 286.25079495
• SMILES: COC(=O)CCCCCCCCCCCCCCCO
• Canonical SMILES: OCCCCCCCCCCCCCCCC(=O)OC
• InChI: InChI=1S/C17H34O3/c1-20-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18/h18H,2-16H2,1H3
• InChIKey: AOTMRIXFFOGWDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 16-hydroxyhexadecanoate
• IUPAC Traditional name: methyl 16-hydroxyhexadecanoate
• Synonyms: MC4 Receptor antagonist; Melanocortin 4 Receptor antagonist; HS028

Database IDs

• MDL Number: MFCD02179660
• PubChem SID: 162247445
• PubChem CID: 3496888

CALCULATED PROPERTIES

• Acid pKa: 16.843943
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.9657984
• LogD (pH = 7.4): 4.9657984
• Log P: 4.9657984
• Molar Refractivity: 83.7814 cm^3
• Polarizability: 33.423153 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: lyophilized powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... POMC(5443)

DETAILS

Sigma Aldrich - H4402

Amino Acid Sequence
Ac-Cys-Glu-His-diCl-D-Phe-Arg-Trp-Gly-Cys-Pro-Pro-Lys-Asp-NH2
Biochem/physiol Actions
HS028 (cyclic [AcCys11, dichloro-D-phenylalanine14, Cys18, Asp-NH2(22)]-beta-MSH11-22) showed high affinity (Ki of 0.95nM) and high (80 fold) MC4 receptor selectivity over the MC3 receptor. HS028 antagonised a alpha-MSH induced increase in cyclic AMP production in transfected cells expressing the MC3 and MC4 receptors, whereas it seemed to be a partial agonist for the MC1 and MC5 receptors. Chronic intracerebroventricularly (i.c.v.) administration of HS028 by osmotic minipumps significantly increased both food intake and body weight in a dose dependent manner without tachyphylaxis for a period of 7 days. This is further evidence that the MC4 receptor is an important mediator of long term weight homeostasis.