(2S)-6-amino-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanamido]-3-(2-methyl-1H-indol-3-yl)propanamido]propanamido]-3-(1H-indol-3-yl)propanamido]-3-phenylpropanamido]hexanamide

• ChemBase ID: 154117
• Molecular Formular: C47H58N12O6
• Molecular Mass: 887.04022
• Monoisotopic Mass: 886.46022764
• SMILES: Cc1c(c2ccccc2[nH]1)C[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N[C@H](Cc1ccccc1)C(=O)N[C@@H](CCCCN)C(=O)N)NC(=O)[C@H](Cc1cnc[nH]1)N
• Canonical SMILES: NCCCC[C@@H](C(=O)N)NC(=O)[C@@H](Cc1ccccc1)NC(=O)[C@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](NC(=O)[C@@H](Cc1c(C)[nH]c2c1cccc2)NC(=O)[C@H](Cc1cnc[nH]1)N)C
• InChI: InChI=1S/C47H58N12O6/c1-27-34(33-15-7-9-17-37(33)54-27)23-41(58-44(62)35(49)22-31-25-51-26-53-31)45(63)55-28(2)43(61)57-40(21-30-24-52-36-16-8-6-14-32(30)36)47(65)59-39(20-29-12-4-3-5-13-29)46(64)56-38(42(50)60)18-10-11-19-48/h3-9,12-17,24-26,28,35,38-41,52,54H,10-11,18-23,48-49H2,1-2H3,(H2,50,60)(H,51,53)(H,55,63)(H,56,64)(H,57,61)(H,58,62)(H,59,65)/t28-,35-,38-,39+,40-,41+/m0/s1
• InChIKey: RVWNMGKSNGWLOL-GIIHNPQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-6-amino-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(1H-imidazol-5-yl)propanamido]-3-(2-methyl-1H-indol-3-yl)propanamido]propanamido]-3-(1H-indol-3-yl)propanamido]-3-phenylpropanamido]hexanamide
• IUPAC Traditional name: (2S)-6-amino-2-[(2R)-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanamido]-3-(2-methyl-1H-indol-3-yl)propanamido]propanamido]-3-(1H-indol-3-yl)propanamido]-3-phenylpropanamido]hexanamide
• Synonyms: HEX; L-Histidyl-2-methyl-D-tryptophyl-L-alanyl-L-tryptophyl-D-phenylalanyl-L-lysinamide; Examorelin; Hexarelin; Hexarelin; L-组氨酰-2-甲基-D-色氨酰-L-丙氨酰-L-色氨酰-D-苯丙氨酰-L-赖氨酰胺; 艾沙瑞林; 海沙瑞林

Database IDs

• CAS Number: 140703-51-1
• PubChem SID: 162248256
• PubChem CID: 6918297

CALCULATED PROPERTIES

• Acid pKa: 11.791179
• H Acceptors: 9
• H Donor: 11
• LogD (pH = 5.5): -5.183351
• LogD (pH = 7.4): -2.73063
• Log P: 0.39507082
• Molar Refractivity: 244.8601 cm^3
• Polarizability: 97.06592 Å^3
• Polar Surface Area: 300.89 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble1 mg/mL, clear, colorless

Safety Information

• RTECS: OL4683333
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC)
• Empirical Formula (Hill Notation): C47H58N12O6

DETAILS

Sigma Aldrich - 80666

Biochem/physiol Actions
Hexarelin (HEX), a ghrelin analogue, is a growth hormone secretagogue receptor agonist, a growth hormone releasing peptide. Hexarelin may be used as an internal standard in quantitative analysis (via chromatography etc.) of prohibited growth hormone enhancing drugs such as GHRP-2. The potential use of Hexarelin as a therapeutic has prompted research studies on its physiological effects in vitro and in vivo.

Toronto Research Chemicals - H294700

Hexarelin is a synthetic growth hormone-releasing peptide (GHRP).

REFERENCES

• Camanni, F., et al.: Front Neuroendocrinol., 19, 47 (1998)
• Ghigo, E., et al.: Eur. J. Endocrinol., 136, 445 (1998)
• Mericq, V., et al.: J. Pediatr. Endocrinol. Metab., 16, 981 (1998)
• Bidlingmaier, M., et al.: Clin. Chem., 55, 445 (1998)
• Thomas, A., et