4-[2-amino-4-(methylsulfanyl)butanamido]-4-({1-[(1-{[4-carbamimidamido-1-({1-[(carboxymethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl}carbamoyl)butyl]carbamoyl}-2-phenylethyl)carbamoyl]-2-(1H-imidazol-5-yl)ethyl}carbamoyl)butanoic acid

• ChemBase ID: 103737
• Molecular Formular: C44H59N13O10S
• Molecular Mass: 962.08536
• Monoisotopic Mass: 961.42285615
• SMILES: CSCCC(N)C(=O)NC(CCC(=O)O)C(=O)NC(Cc1c[nH]cn1)C(=O)NC(Cc1ccccc1)C(=O)NC(CCCNC(=N)N)C(=O)NC(Cc1c[nH]c2c1cccc2)C(=O)NCC(=O)O
• Canonical SMILES: CSCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)O)Cc1c[nH]c2c1cccc2)CCCNC(=N)N)Cc1ccccc1)Cc1nc[nH]c1)CCC(=O)O)N
• InChI: InChI=1S/C44H59N13O10S/c1-68-17-15-29(45)38(62)53-32(13-14-36(58)59)41(65)57-35(20-27-22-48-24-52-27)43(67)55-33(18-25-8-3-2-4-9-25)42(66)54-31(12-7-16-49-44(46)47)40(64)56-34(39(63)51-23-37(60)61)19-26-21-50-30-11-6-5-10-28(26)30/h2-6,8-11,21-22,24,29,31-35,50H,7,12-20,23,45H2,1H3,(H,48,52)(H,51,63)(H,53,62)(H,54,66)(H,55,67)(H,56,64)(H,57,65)(H,58,59)(H,60,61)(H4,46,47,49)
• InChIKey: HAAUASBAIUJHAN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[2-amino-4-(methylsulfanyl)butanamido]-4-({1-[(1-{[4-carbamimidamido-1-({1-[(carboxymethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl}carbamoyl)butyl]carbamoyl}-2-phenylethyl)carbamoyl]-2-(1H-imidazol-5-yl)ethyl}carbamoyl)butanoic acid; 4-[2-amino-4-(methylsulfanyl)butanamido]-4-({1-[(1-{[4-carbamimidamido-1-({1-[(carboxymethyl)carbamoyl]-2-(1H-indol-3-yl)ethyl}carbamoyl)butyl]carbamoyl}-2-phenylethyl)carbamoyl]-2-(1H-imidazol-4-yl)ethyl}carbamoyl)butanoic acid
• IUPAC Traditional name: 4-[2-amino-4-(methylsulfanyl)butanamido]-4-{[1-({1-[(4-carbamimidamido-1-{[1-(carboxymethylcarbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}butyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(3H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid; 4-[2-amino-4-(methylsulfanyl)butanamido]-4-{[1-({1-[(4-carbamimidamido-1-{[1-(carboxymethylcarbamoyl)-2-(1H-indol-3-yl)ethyl]carbamoyl}butyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(1H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid
• Synonyms: ACTH4-10; Adrenocorticotropic Hormone Fragment 4-10 human, rat; Met-Glu-His-Phe-Arg-Trp-Gly; ADRENOCORTICOTROPIC HORMONE, Fragment 4-10

Database IDs

• CAS Number: 4037-01-8
• MDL Number: MFCD00167482
• PubChem SID: 24890423; 162091396
• PubChem CID: 4260043

CALCULATED PROPERTIES

• Acid pKa: 3.219987
• H Acceptors: 15
• H Donor: 14
• LogD (pH = 5.5): -6.777318
• LogD (pH = 7.4): -6.376066
• Log P: -6.405425
• Molar Refractivity: 258.9789 cm^3
• Polarizability: 97.27683 Å^3
• Polar Surface Area: 381.59 Å^2
• Rotatable Bonds: 29
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C
• 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 ... POMC(5443)rat ... Crhr2(64680)

Product Information

• Purity: ≥97% (HPLC)

DETAILS

Sigma Aldrich - A0401

Amino Acid Sequence
Met-Glu-His-Phe-Arg-Trp-Gly
Other Notes
Core fragment of ACTH, α- and β-MSH, and β-lipotropin
Quality
Lacks adrenocorticotropic activity.
Biochem/physiol Actions
Adrenocorticotropic Hormone Fragment 4-10 (ACTH (4-10)) attenuates ischemia/reperfusion-induced cardiac injury via reduction in infarct size, caspase 3 activity, and apoptosis, and an increase in HO-1 expression. ACTH 4-10 is a melanocortin 4 receptor (MCR-4) agonist. ACTH 4-10 facilitates active and passive avoidance acquisition, improves short term memory consolidation, and promotes memory retrieval. ACTH 4-10 and semax are analogues.

REFERENCES

• Greven, H.M. and DeWied D., Eur. J. Pharmacol., 2: 14, (1967).
• Wolthius, O.L. and DeWied D., Pharmacol. Biochem. Behavior, 4: 273, (1978).