(2S)-2-[(2S)-2-[(2S)-2-butanamido-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamido-N-[(1S)-1-[(carbamoylmethyl)(methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]pentanamide

• ChemBase ID: 153997
• Molecular Formular: C39H52N12O6
• Molecular Mass: 784.90698
• Monoisotopic Mass: 784.41327744
• SMILES: CCCC(=O)N[C@@H](Cc1c[nH]cn1)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)N[C@@H](Cc1c[nH]c2c1cccc2)C(=O)N(C)CC(=O)N
• Canonical SMILES: CCCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N(CC(=O)N)C)Cc1c[nH]c2c1cccc2)CCCNC(=N)N)Cc1ccccc1)Cc1c[nH]cn1
• InChI: InChI=1S/C39H52N12O6/c1-3-10-34(53)47-31(19-26-21-43-23-46-26)37(56)49-30(17-24-11-5-4-6-12-24)36(55)48-29(15-9-16-44-39(41)42)35(54)50-32(38(57)51(2)22-33(40)52)18-25-20-45-28-14-8-7-13-27(25)28/h4-8,11-14,20-21,23,29-32,45H,3,9-10,15-19,22H2,1-2H3,(H2,40,52)(H,43,46)(H,47,53)(H,48,55)(H,49,56)(H,50,54)(H4,41,42,44)/t29-,30-,31-,32-/m0/s1
• InChIKey: NINOPZAAGJJNAR-YDPTYEFTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-butanamido-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamido-N-[(1S)-1-[(carbamoylmethyl)(methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]pentanamide
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-butanamido-3-(1H-imidazol-4-yl)propanamido]-3-phenylpropanamido]-5-carbamimidamido-N-[(1S)-1-[carbamoylmethyl(methyl)carbamoyl]-2-(1H-indol-3-yl)ethyl]pentanamide
• Synonyms: Butir-His-D-Phe-Arg-Trp-Sar-NH2 trifluoroacetate salt; Ro 27-3225 trifluoroacetate salt; Butir-His-D-Phe-Arg-Trp-Sar-NH2 三氟乙酸盐; Ro273225 三氟乙酸盐

Database IDs

• MDL Number: MFCD04112656
• PubChem SID: 162248136
• PubChem CID: 9962372

CALCULATED PROPERTIES

• Acid pKa: 11.546089
• H Acceptors: 10
• H Donor: 10
• LogD (pH = 5.5): -4.0416946
• LogD (pH = 7.4): -3.3037512
• Log P: -1.3592912
• Molar Refractivity: 221.3299 cm^3
• Polarizability: 82.34486 Å^3
• Polar Surface Area: 286.17 Å^2
• Rotatable Bonds: 22
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white lyophilized solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (reversed phase HPLC)
• Empirical Formula (Hill Notation): C39H52N12O6 · xC2HF3O2

DETAILS

Sigma Aldrich - R3905

Amino Acid Sequence
Butir-His-Phe-Arg-Trp-Sar-NH2
Biochem/physiol Actions
Ro 27-3225 is a selective melanocortin MC4 receptor agonist. EC50 = 1 nM. Ro 27-3225 shows some activity at the MC1 receptor. Ro 27-3225 reverses hemorrhagic shock, reduces multiple organ damage, and improves survival. Ro 27-3225 may have a protective role against multiple organ failure following circulatory shock. Ro 27-3225 also reduces food intake in ob/ob mice.