2-{[1-(2-amino-3-methylpentanoyl)pyrrolidin-2-yl]formamido}-3-methylpentanoic acid

• ChemBase ID: 103866
• Molecular Formular: C17H31N3O4
• Molecular Mass: 341.44574
• Monoisotopic Mass: 341.23145649
• SMILES: CCC(C)C(N)C(=O)N1CCCC1C(=O)NC(C(C)CC)C(=O)O
• Canonical SMILES: CCC(C(C(=O)O)NC(=O)C1CCCN1C(=O)C(C(CC)C)N)C
• InChI: InChI=1S/C17H31N3O4/c1-5-10(3)13(18)16(22)20-9-7-8-12(20)15(21)19-14(17(23)24)11(4)6-2/h10-14H,5-9,18H2,1-4H3,(H,19,21)(H,23,24)
• InChIKey: JNTMAZFVYNDPLB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[1-(2-amino-3-methylpentanoyl)pyrrolidin-2-yl]formamido}-3-methylpentanoic acid
• IUPAC Traditional name: diprotin A
• Synonyms: Ile-Pro-Ile; Diprotin A; ILE-PRO-ILE

Database IDs

• CAS Number: 90614-48-5
• MDL Number: MFCD00038707
• PubChem SID: 162103020; 24896160
• PubChem CID: 3107

CALCULATED PROPERTIES

• Acid pKa: 3.5953424
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.9808482
• LogD (pH = 7.4): -1.0360115
• Log P: -0.97957426
• Molar Refractivity: 89.9744 cm^3
• Polarizability: 35.810993 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C
• RTECS: NR4737000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97% (HPLC)

DETAILS

MP Biomedicals - 02153132

An inhibitor of dipeptidyl aminopeptidase IV.

Sigma Aldrich - I9759

Amino Acid Sequence
Ile-Pro-Ile
Biochem/physiol Actions
Inhibitor of dipeptidyl peptidase IV. Inhibits entry of HIV-1 or HIV-2 into T lymphoblastoid and monocytoid cell lines.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. I9759.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Umezawa, H., et al., J. Antibiot., 37: 422, (1985).