(2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-3-carbamoyl-2-[(2S)-3-methyl-2-[(2S)-pyrrolidin-2-ylformamido]butanamido]propanamido]-3-phenylpropanamido]hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanoic acid; trifluoroacetic acid

• ChemBase ID: 154857
• Molecular Formular: C55H78F3N13O14
• Molecular Mass: 1202.2817296
• Monoisotopic Mass: 1201.5743289
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1c[nH]cn1)C(=O)O)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CCCCN)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@H](CC(=O)N)NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.NCCCC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)Cc1nc[nH]c1)CO)CC(C)C)Cc1ccccc1)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](C(C)C)NC(=O)[C@@H]1CCCN1)CC(=O)N)Cc1ccccc1
• InChI: InChI=1S/C53H77N13O12.C2HF3O2/c1-30(2)22-37(47(71)65-42(28-67)51(75)64-41(53(77)78)25-34-27-56-29-58-34)60-49(73)39(24-33-16-9-6-10-17-33)61-46(70)36(18-11-12-20-54)59-48(72)38(23-32-14-7-5-8-15-32)62-50(74)40(26-43(55)68)63-52(76)44(31(3)4)66-45(69)35-19-13-21-57-35;3-2(4,5)1(6)7/h5-10,14-17,27,29-31,35-42,44,57,67H,11-13,18-26,28,54H2,1-4H3,(H2,55,68)(H,56,58)(H,59,72)(H,60,73)(H,61,70)(H,62,74)(H,63,76)(H,64,75)(H,65,71)(H,66,69)(H,77,78);(H,6,7)/t35-,36-,37-,38-,39-,40-,41-,42-,44-;/m0./s1
• InChIKey: FXBODCREWDDYNR-DFZCIRLNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-3-carbamoyl-2-[(2S)-3-methyl-2-[(2S)-pyrrolidin-2-ylformamido]butanamido]propanamido]-3-phenylpropanamido]hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2S)-2-[(2S)-6-amino-2-[(2S)-2-[(2S)-3-carbamoyl-2-[(2S)-3-methyl-2-[(2S)-pyrrolidin-2-ylformamido]butanamido]propanamido]-3-phenylpropanamido]hexanamido]-3-phenylpropanamido]-4-methylpentanamido]-3-hydroxypropanamido]-3-(1H-imidazol-4-yl)propanoic acid; trifluoroacetic acid
• Synonyms: Hemopressin from rat brain; Hemopressin from rat; L-Prolyl-L-valyl-L-asparaginyl-L-phenylalanyl-L-lysyl-L-phenylalanyl-L-leucyl-L-seryl-L-histidine trifluoroacetate salt; Pro-Val-Asn-Phe-Lys-Phe-Leu-Ser-His trifluoroacetate salt; Hemopressin trifluoroacetate salt

Database IDs

• CAS Number: 568588-77-2(freebase)
• MDL Number: MFCD19443861
• PubChem SID: 162248995
• PubChem CID: 71312009

CALCULATED PROPERTIES

• Acid pKa: 3.0745199
• H Acceptors: 15
• H Donor: 14
• LogD (pH = 5.5): -8.213717
• LogD (pH = 7.4): -6.341079
• Log P: -4.534414
• Molar Refractivity: 282.0602 cm^3
• Polarizability: 110.84002 Å^3
• Polar Surface Area: 400.15 Å^2
• Rotatable Bonds: 34
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: ≥2 mg/mL
• Apperance: white to off-white powder

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C53H77N13O12 · xC2HF3O2

DETAILS

Sigma Aldrich - H3042

Biochem/physiol Actions
Hemopressin is an endogenous hypotensive nonapeptide derived from hemoglobin. Hemopressin reduces appetite, acting as a cannabinoid CB1 inverse agonist. It blocks signaling by CB(1) receptors but not by other members of family A G protein-coupled receptors (including the closely related CB(2) receptors.