N-hydroxy-N'-{1-[2-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}-2-pentylbutanediamide

• ChemBase ID: 104087
• Molecular Formular: C19H35N3O5
• Molecular Mass: 385.4983
• Monoisotopic Mass: 385.25767124
• SMILES: CCCCCC(CC(=O)NO)C(=O)NC(C(C)C)C(=O)N1CCCC1CO
• Canonical SMILES: CCCCCC(C(=O)NC(C(=O)N1CCCC1CO)C(C)C)CC(=O)NO
• InChI: InChI=1S/C19H35N3O5/c1-4-5-6-8-14(11-16(24)21-27)18(25)20-17(13(2)3)19(26)22-10-7-9-15(22)12-23/h13-15,17,23,27H,4-12H2,1-3H3,(H,20,25)(H,21,24)
• InChIKey: XJLATMLVMSFZBN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-hydroxy-N'-{1-[2-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}-2-pentylbutanediamide
• IUPAC Traditional name: N-hydroxy-N'-{1-[2-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}-2-pentylbutanediamide; actinonin
• Synonyms: 3-[[1-[(2-(Hydroxymethyl)-1-pyrrolidinyl)carbonyl]-2-methylpropyl]carbamoyl]octanohydroxamic acid; Actinonin; 3-[[1-[[2-(Hydroxymethyl)-1-pyrolidinyl]carbonyl]-2-methyl-propyl]carbamoyl]octano-hydroxamic acid; ACTINONIN

Database IDs

• CAS Number: 13434-13-4
• MDL Number: MFCD00080257
• Beilstein Number: 1555250
• PubChem SID: 24278232; 162091407
• PubChem CID: 2020

CALCULATED PROPERTIES

• Acid pKa: 8.899384
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 0.879329
• LogD (pH = 7.4): 0.8660266
• Log P: 0.8795019
• Molar Refractivity: 101.5144 cm^3
• Polarizability: 39.930626 Å^3
• Polar Surface Area: 118.97 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: RG9900700
• 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 ... ANPEP(290), DPP4(1803), ECE1(1889), LAP3(51056)

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C19H35N3O5

DETAILS

MP Biomedicals - 02154712

(3-[[1-[[2-(Hydroxymethyl)-1-pyrolidinyl]carbonyl]-2-methyl- propyl]carbamoyl]octano- hydroxamic acid) Inhibitor of aminopeptidase M and leucine aminopeptidase.

Sigma Aldrich - A6671

Biochem/physiol Actions
Inhibitor of leucine aminopeptidase.
Application
Actinonin is an inhibitor of leucine aminopeptidase. Actinonin has also been used to improve antibacterial activity and antiobesity therapeutics.

Sigma Aldrich - 01809

Biochem/physiol Actions
Inhibitor of leucine aminopeptidase.
Other Notes
Aminopeptidase inhibitor1,2

REFERENCES

• Umezawa, H., et al., J. Antibiot.,38: 1629, (1985).