Chemical Identifiers & Names

• INN: Elamipretide
• Synonyms: SS‑31, MTP‑131, Bendavia, SBT‑272
• CAS Number: 736992‑21‑5
• PubChem CID: 11764719
• UNII: 87GWG91S09
• KEGG ID: D10925

Molecular Formula & Mass

• Formula: C₃₂H₄₉N₉O₅
• Molecular Weight: ~639.8 g/mol

IUPAC Name

(2S)-6-Amino-2-[[(2S)-2-[[(2R)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]-
3-(4-hydroxy-2,6-dimethylphenyl)propanoyl]amino]-N-[(2S)-1-amino-1-oxo-3-
phenylpropan-2-yl]hexanamide

Peptide Sequence & Residues

• Sequence: D‑Arg‑Dmt‑Lys‑Phe‑NH₂ (2,6‑dimethyltyrosine)
• Net Charge (physiological pH): +3
• Classification: Aromatic‑basic tetrapeptide with alternating residues

SMILES, InChI & InChIKey

• SMILES:
  CC1=C(CC(NC(=O)C(N)CCCNC(N)=N)C(=O)NC(CCCCN)C(=O)NC(CC2=CC=CC=C2)C(N)=O)C(=CC(=C1)O)C
• InChI:
  1S/C32H49N9O5/c1-19-15-22(42)16-20(2)… (full available via PubChem CID 11764719)
• InChIKey: SFVLTCAESLKEHH-WKAQUBQDSA-N

Structural & Physicochemical Properties

• Solubility (25 °C): ~100 mg/mL in water (~156 mM) per SelleckChem datasheet :contentReference[oaicite:1]{index=1}
• Purity: ≥ 99% (HPLC) common in research-use batches :contentReference[oaicite:2]{index=2}
• Appearance: Lyophilized powder, stored at −20 °C (long‑term stability) :contentReference[oaicite:3]{index=3}
• Storage (solvent): Typically stable at −80 °C for months, −20 °C up to a month :contentReference[oaicite:4]{index=4}

Molecular Behavior & Interactions

• Strong binding affinity for cardiolipin in mitochondrial inner membranes; formed via electrostatic & hydrophobic interactions :contentReference[oaicite:5]{index=5}
• Interacts with cytochrome c peroxidase activity: inhibits cardiolipin oxidation via heme iron protection :contentReference[oaicite:6]{index=6}
• Reported ability to accumulate inside mitochondria at high local concentrations, supported by electrochemical potential and charge :contentReference[oaicite:7]{index=7}

Additional Chemical Forms (Acetate Salt)

• Molecular Formula (acetate): C₃₄H₅₃N₉O₇
• Molecular Weight: ~699.8 g/mol
• CAS Number: 1334953‑95‑5
• InChIKey: UEYRJRBULBAAEG‑NFWUDPOKSA‑N
• SMILES: includes both base peptide and acetate moiety :contentReference[oaicite:8]{index=8}

Key Structural Features

• Amino acid sequence includes D‑arginine at N‑terminus and Dmt residue for oxidative resilience :contentReference[oaicite:9]{index=9}
• Alternating aromatic (Dmt, Phe) and basic (Arg, Lys) residues promote membrane binding and mitochondrial localization :contentReference[oaicite:10]{index=10}
• Net positive charge enhances mitochondria targeting driven by membrane potential :contentReference[oaicite:11]{index=11}

References

1. Wikipedia: Elamipretide article—chemical identifiers, IUPAC, formula, sequence, SMILES/InChIKey :contentReference[oaicite:12]{index=12}
2. SelleckChem datasheet—molecular weight, solubility, storage, SMILES, biological interaction notes :contentReference[oaicite:13]{index=13}
3. InvivoChem product data—acetate form formula, weight, InChIKey, SMILES :contentReference[oaicite:14]{index=14}
4. International Peptide Society monograph—sequence, formula, weight, structural behavior :contentReference[oaicite:15]{index=15}
5. ProbeChem product specs—purity, formula, storage, chemical name/SMILES :contentReference[oaicite:16]{index=16}