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

• ChemBase ID: 153384
• Molecular Formular: C51H65N13O11S
• Molecular Mass: 1068.2073
• Monoisotopic Mass: 1067.46472097
• SMILES: CSCCC(C(=O)NC(CCC(=O)O)C(=O)NC(Cc1cnc[nH]1)C(=O)NC(Cc1ccccc1)C(=O)NC(CCCNC(=N)N)C(=O)NC(Cc1c[nH]c2c1cccc2)C(=O)O)NC(=O)C(Cc1ccc(cc1)O)N
• Canonical SMILES: CSCCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)O)Cc1c[nH]c2c1cccc2)CCCNC(=N)N)Cc1ccccc1)Cc1[nH]cnc1)CCC(=O)O)NC(=O)C(Cc1ccc(cc1)O)N
• InChI: InChI=1S/C51H65N13O11S/c1-76-21-19-39(59-44(68)35(52)22-30-13-15-33(65)16-14-30)47(71)61-38(17-18-43(66)67)46(70)63-41(25-32-27-55-28-58-32)49(73)62-40(23-29-8-3-2-4-9-29)48(72)60-37(12-7-20-56-51(53)54)45(69)64-42(50(74)75)24-31-26-57-36-11-6-5-10-34(31)36/h2-6,8-11,13-16,26-28,35,37-42,57,65H,7,12,17-25,52H2,1H3,(H,55,58)(H,59,68)(H,60,72)(H,61,71)(H,62,73)(H,63,70)(H,64,69)(H,66,67)(H,74,75)(H4,53,54,56)
• InChIKey: LABZPEAYQTYYEF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-4-(methylsulfanyl)butanamido}-4-{[1-({1-[(4-carbamimidamido-1-{[1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}butyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(1H-imidazol-5-yl)ethyl]carbamoyl}butanoic acid
• IUPAC Traditional name: 4-{2-[2-amino-3-(4-hydroxyphenyl)propanamido]-4-(methylsulfanyl)butanamido}-4-{[1-({1-[(4-carbamimidamido-1-{[1-carboxy-2-(1H-indol-3-yl)ethyl]carbamoyl}butyl)carbamoyl]-2-phenylethyl}carbamoyl)-2-(3H-imidazol-4-yl)ethyl]carbamoyl}butanoic acid
• Synonyms: Adrenocorticotropic Hormone Tyr-Fragment 4-9 human, rat

Database IDs

• CAS Number: 129813-57-6
• MDL Number: MFCD00133037
• PubChem SID: 162247523; 24891186
• PubChem CID: 4168166

CALCULATED PROPERTIES

• Acid pKa: 3.2306736
• H Acceptors: 16
• H Donor: 15
• LogD (pH = 5.5): -4.8514175
• LogD (pH = 7.4): -4.534797
• Log P: -4.5183992
• Molar Refractivity: 290.0727 cm^3
• Polarizability: 109.28437 Å^3
• Polar Surface Area: 401.82 Å^2
• Rotatable Bonds: 31
• Lipinski's Rule of Five: false

PROPERTIES

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 ... POMC(5443)

Product Information

• Purity: ≥97% (HPLC)
• Empirical Formula (Hill Notation): C51H65N13O11S

DETAILS

Sigma Aldrich - A7181

Amino Acid Sequence
Tyr-Met-Glu-His-Phe-Arg-Trp
Biochem/physiol Actions
Analog of ACTH (4-9) that can be iodinated for receptor and histochemical studies