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230961-08-7 molecular structure
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(2R)-N-[(1S)-2,2-dimethyl-1-{[(1R)-1-phenylethyl]carbamoyl}propyl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide

ChemBase ID: 154905
Molecular Formular: C34H43N3O4
Molecular Mass: 557.72292
Monoisotopic Mass: 557.32535687
SMILES and InChIs

SMILES:
Cc1cc(ccc1c1ccccc1)CCC[C@H](CC(=O)NO)C(=O)N[C@H](C(=O)N[C@H](C)c1ccccc1)C(C)(C)C
Canonical SMILES:
ONC(=O)C[C@H](C(=O)N[C@@H](C(C)(C)C)C(=O)N[C@@H](c1ccccc1)C)CCCc1ccc(c(c1)C)c1ccccc1
InChI:
InChI=1S/C34H43N3O4/c1-23-21-25(19-20-29(23)27-16-10-7-11-17-27)13-12-18-28(22-30(38)37-41)32(39)36-31(34(3,4)5)33(40)35-24(2)26-14-8-6-9-15-26/h6-11,14-17,19-21,24,28,31,41H,12-13,18,22H2,1-5H3,(H,35,40)(H,36,39)(H,37,38)/t24-,28-,31-/m1/s1
InChIKey:
JJHRUUKMPWUYIB-HVOSOHGQSA-N

Cite this record

CBID:154905 http://www.chembase.cn/molecule-154905.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(2R)-N-[(1S)-2,2-dimethyl-1-{[(1R)-1-phenylethyl]carbamoyl}propyl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide
IUPAC Traditional name
(2R)-N-[(1S)-2,2-dimethyl-1-{[(1R)-1-phenylethyl]carbamoyl}propyl]-N'-hydroxy-2-[3-(3-methyl-4-phenylphenyl)propyl]butanediamide
Synonyms
(2R)-N1-[(1S)-2,2-Dimethyl-1-({[(1R)-1-phenylethyl]amino}carbonyl)propyl]-2-{3-[(3-methyl-4-phenyl)-phenyl]propyl}-(N4-hydroxy)butanediamide
UK-356,618
UK-356618
(2R)-N1-[(1S)-2,2-Dimethyl-1-[[[(1R)-1-phenylethyl]amino]carbonyl]propyl]-N4-hydroxy-2-[3-(2-methyl[1,1'-biphenyl]-4-yl)propyl]butanediamide
UK 356618
PF-03890101
UK-356618
CAS Number
230961-08-7
MDL Number
MFCD19443865
PubChem SID
162249043
PubChem CID
10370504

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 10370504 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 8.899392  H Acceptors
H Donor LogD (pH = 5.5) 6.249121 
LogD (pH = 7.4) 6.2358193  Log P 6.2492943 
Molar Refractivity 162.2151 cm3 Polarizability 64.43837 Å3
Polar Surface Area 107.53 Å2 Rotatable Bonds 13 
Lipinski's Rule of Five false 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
DMSO: ≥25 mg/mL expand Show data source
Methanol expand Show data source
Apperance
Beige Solid expand Show data source
white to tan powder expand Show data source
Melting Point
95-105°C expand Show data source
Optical Rotation
[α]/D >+25.0°, c = 0.5 in methanol expand Show data source
Storage Condition
-20°C Freezer expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Purity
≥98% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C34H43N3O4 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - PZ0152 external link
Legal Information
Sold for research purposes under agreement from Pfizer Inc.
Biochem/physiol Actions
UK-356,618 is a potent, selective inhibitor of Matrix metalloproteinase MMP3 (stromelysin-1). MMP-3 IC50 = 5.9 nM, selectivity is 140-fold vs MMP-1, -2, -9, and -14.
Toronto Research Chemicals - U700585 external link
Potent and selective inhibitor of matrix metalloprotease-3 (MMP-3) (IC50 = 5.9 nM). Displays selectivity over a range of MMPs (IC50 values are 73, 840, 1790, 1900 and 51000 for MMP-13, MMP-9, MMP-2, MMP-14 and MMP-1 respectively).

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Fray, M.J. et al.: Bioorg. Med. Chem. Lett., 11, 571 (2001)
  • • Fray, M.J. et al.: J. Med. Chem., 46, 3514 (2001)
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PATENTS

PATENTS

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INTERNET

INTERNET

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