(2S)-2-{[(2S)-2-[(2R)-3-(1H-indol-3-yl)-2-[(2S)-2-[(2R)-3-(1H-indol-3-yl)-2-[(2R)-2-(methylamino)-3-phenylpropanamido]propanamido]-3-phenylpropanamido]propanamido]-4-methylpentyl]amino}-4-methylpentanamide

• ChemBase ID: 131705
• Molecular Formular: C53H67N9O5
• Molecular Mass: 910.15638
• Monoisotopic Mass: 909.52651629
• SMILES: CC(C)C[C@@H](CN[C@@H](CC(C)C)C(=O)N)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@H](Cc1ccccc1)NC(=O)[C@@H](Cc1c[nH]c2c1cccc2)NC(=O)[C@@H](Cc1ccccc1)NC
• Canonical SMILES: CN[C@@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](CC(C)C)CN[C@H](C(=O)N)CC(C)C)Cc1c[nH]c2c1cccc2)Cc1ccccc1)Cc1c[nH]c2c1cccc2)Cc1ccccc1
• InChI: InChI=1S/C53H67N9O5/c1-33(2)24-39(32-58-44(49(54)63)25-34(3)4)59-51(65)47(28-37-30-56-42-22-14-12-20-40(37)42)62-52(66)46(27-36-18-10-7-11-19-36)60-53(67)48(29-38-31-57-43-23-15-13-21-41(38)43)61-50(64)45(55-5)26-35-16-8-6-9-17-35/h6-23,30-31,33-34,39,44-48,55-58H,24-29,32H2,1-5H3,(H2,54,63)(H,59,65)(H,60,67)(H,61,64)(H,62,66)/t39-,44-,45+,46-,47+,48+/m0/s1
• InChIKey: BFHMRHNHBXKAPC-ICXWOUFDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(2S)-2-[(2R)-3-(1H-indol-3-yl)-2-[(2S)-2-[(2R)-3-(1H-indol-3-yl)-2-[(2R)-2-(methylamino)-3-phenylpropanamido]propanamido]-3-phenylpropanamido]propanamido]-4-methylpentyl]amino}-4-methylpentanamide
• IUPAC Traditional name: (2S)-2-{[(2S)-2-[(2R)-3-(1H-indol-3-yl)-2-[(2S)-2-[(2R)-3-(1H-indol-3-yl)-2-[(2R)-2-(methylamino)-3-phenylpropanamido]propanamido]-3-phenylpropanamido]propanamido]-4-methylpentyl]amino}-4-methylpentanamide
• Synonyms: Methyl-D-Phe-D-Trp-Phe-D-Trp-Leu-psi[CH2NH]-Leu-NH2; [Methyl-D-Phe6, D-Trp7,9, Leu10-psi(CH2NH)Leu11]-Substance P Fragment 6-11

Database IDs

• CAS Number: 152369-60-3
• MDL Number: MFCD00792897
• PubChem SID: 162225982
• PubChem CID: 10350790

CALCULATED PROPERTIES

• Acid pKa: 12.058182
• H Acceptors: 7
• H Donor: 9
• LogD (pH = 5.5): 0.7417087
• LogD (pH = 7.4): 4.1052756
• Log P: 6.284072
• Molar Refractivity: 261.4231 cm^3
• Polarizability: 104.682434 Å^3
• Polar Surface Area: 215.13 Å^2
• Rotatable Bonds: 25
• 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 ... TAC1(6863)

Product Information

• Purity: ≥97% (HPLC)
• Compostion: Peptide content, ~70%

DETAILS

Sigma Aldrich - S3922

Biochem/physiol Actions
This substance P analog inhibited small-cell lung cancer proliferation in vitro and in vivo.