Ubenimex

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Names

[ Name ]:
Ubenimex

[Synonym ]:
BESTATIN
BENIMEX
Bestatin,UbeniMex
2-(3-Amino-2-hydroxy-4-phenyl-butyrylamino)-4-methyl-pentanoic acid
Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-
nk421
MFCD00083262
N-(3-Amino-2-hydroxy-4-phenylbutanoyl)leucine
EINECS 261-529-2

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
604.7±55.0 °C at 760 mmHg

[ Melting Point ]:
245 °C (dec.)(lit.)

[ Molecular Formula ]:
C₁₆H₂₄N₂O₄

[ Molecular Weight ]:
308.373

[ Flash Point ]:
319.5±31.5 °C

[ Exact Mass ]:
308.173615

[ PSA ]:
112.65000

[ LogP ]:
2.64

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.557

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OH2915000

CHEMICAL NAME :: L-Leucine, N-(3-amino-2-hydroxy-1-oxo-4-phenylbutyl)-, (S-(R*,S*))-

CAS REGISTRY NUMBER :: 58970-76-6

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C16-H24-N2-O4

MOLECULAR WEIGHT :: 308.42

WISWESSER LINE NOTATION :: 1Y1&1YVQMVYQYZ1R

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 780 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1900 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 190 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1300 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Skin and Appendages - hair Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >1200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 36,2971,1983 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 63700 mg/kg/91D-C

TOXIC EFFECTS :: Kidney, Ureter, Bladder - proteinuria

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,401,1984 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 1250 mg/kg

SEX/DURATION :: female 16-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - extra-embryonic structures (e.g., placenta, umbilical cord) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: HMMRA2 Hormone and Metabolic Research. (Georg Thieme Verlag, Postfach 732, D-7000 Stuttgart 1, Fed. Rep. Ger.) V.1- 1969- Volume(issue)/page/year: 21,366,1989

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
OH2915000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

N-[(2S,3S)-3-azido-2-hydroxy-4-phenylbutanoyl]-L-leucine benzyl ester
E3 ligase Ligand 9
benzyl N-[(2S,3R)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutanoyl]-L-leucinate
methyl N-{(2S,3R)-2-O-benzyl-4-phenyl-3-[9-phenyl-9-fluorenyl-amino]-butanoyl}-L-leucine
(2S,3R)-3-(((BENZYLOXY)CARBONYL)AMINO)-2-HYDROXY-4-PHENYLBUTANOIC ACID
Cbz-D-Phenylalaninol
Z-D-Phe-OH
Benzyl [(2R)-1-oxo-3-phenyl-2-propanyl]carbamate
Benzyl L-leucinate hydrochloride (1:1)

DownStream

Articles

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PLoS ONE 7(12) , e51072, (2012)

Chemerin is a leukocyte chemoattractant and adipokine with important immune and metabolic roles. Chemerin, secreted in an inactive form prochemerin, undergoes C-terminal proteolytic cleavage to genera...

Gingipain aminopeptidase activities in Porphyromonas gingivalis.

Biol. Chem. 393(12) , 1471-6, (2012)

Bestatin, a specific inhibitor of metalloaminopeptidases,inhibits the growth of Porphyromonas gingivalis. To identify its target enzyme, a library of fluorescent substrates was used but no metalloamin...

Preparation and evaluation of a new releasable PEGylated tumor necrosis factor-α (TNF-α) conjugate for therapeutic application.

Sci. China Life Sci. 56(1) , 51-8, (2013)

To design a releasable PEGylated TNF-α (rPEG-TNF-α), a cathepsin B-sensitive dipeptide (Val-Cit moiety) was inserted into conventional PEG-modified TNF-α (PEG-TNF-α), facilitating its clinical use for...

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