ChemComp-R45: N-{(2S)-3-[(S)-(4-bromophenyl)(hydroxy)phosphoryl]-2-[(3-phenyl-1...

Basic information

• Entry: Database: PDB chemical components / ID: R45
• Name: Name: N-{(2S)-3-[(S)-(4-bromophenyl)(hydroxy)phosphoryl]-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]propanoyl}-L-alpha-glutamyl-L-al; Synonyms: RXP470A

BIRD information

• Type: Peptide-like / Enzyme inhibitor
• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• RXP470A (PDB)

Annotation

• Function: inhibitor of Macrophage metalloelastase, EC: 3.4.24.65EC: inhibitor of Macrophage metalloelastase, EC: 3.4.24.65 / Info source: PubMed: 23343195

External info

• PubChem: 70698423

Family

phosphinic acid containing, zinc-binding metalloproteinase inhibitor

N-[(2S)-3-[(S)-(4-BROMOPHENYL)(HYDROXY)PHOSPHORYL]-2-{[3-(3'-CHLOROBIPHENYL-4-YL)-1,2-OXAZOL-5-YL]METHYL}PROPANOYL]-L-ALPHA-GLUTAMYL-L-ALPHA-GLUTAMINE / N-[(2S)-3-[(R)-(4-BROMOPHENYL)(HYDROXY)PHOSPHORYL]-2-{[3-(3'-CHLOROBIPHENYL-4-YL)-1,2-OXAZOL-5-YL]METHYL}PROPANOYL]-L-ALANYL-L-ALANINAMIDE / N-{(2S)-3-[(S)-(4-BROMOPHENYL)(HYDROXY)PHOSPHORYL]-2-[(3-PHENYL-1,2-OXAZOL-5-YL)METHYL]PROPANOYL}-L-ALPHA-GLUTAMYL-L-ALPHA-GLUTAMINE / N-{(2S)-3-[(R)-(4-BROMOPHENYL)(HYDROXY)PHOSPHORYL]-2-[(3-PHENYL-1,2-OXAZOL-5-YL)METHYL]PROPANOYL}-L-ALANYL-L-ALANINAMIDE

Chemical information

Composition

Formula: C₂₉H₃₂BrN₄O₁₀P / Number of atoms: 77 / Formula weight: 707.463 / Formal charge: 0

Others

4gr3

14E

GLU

GLU

NH2

Type: peptide-like / PDB classification: HETAIN / Three letter code: R45 / Ideal coordinates details: Corina / Model coordinates PDB-ID: 4GR3 / Subcomponent: 14E, GLU, GLU, NH2

History

Create component	Oct 4, 2012
Initial release	Feb 1, 2013
Modify synonyms	Jun 5, 2020

• External links: UniChem / ChemSpider / BindingDB / ChEMBL / PubChem / PubChem_TPharma / ZINC / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(O)CCC(C(=O)N)NC(=O)C(NC(=O)C(CP(=O)(O)c1ccc(Br)cc1)Cc3onc(c2ccccc2)c3)CCC(=O)O
• CACTVS 3.370: NC(=O)[CH](CCC(O)=O)NC(=O)[CH](CCC(O)=O)NC(=O)[CH](Cc1onc(c1)c2ccccc2)C[P](O)(=O)c3ccc(Br)cc3
• OpenEye OEToolkits 1.7.6: c1ccc(cc1)c2cc(on2)CC(CP(=O)(c3ccc(cc3)Br)O)C(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)N

SMILES CANONICAL

• CACTVS 3.370: NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](Cc1onc(c1)c2ccccc2)C[P](O)(=O)c3ccc(Br)cc3
• OpenEye OEToolkits 1.7.6: c1ccc(cc1)c2cc(on2)C[C@H](CP(=O)(c3ccc(cc3)Br)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N

InChI

• InChI 1.03: InChI=1S/C29H32BrN4O10P/c30-19-6-8-21(9-7-19)45(42,43)16-18(14-20-15-24(34-44-20)17-4-2-1-3-5-17)28(40)33-23(11-13-26(37)38)29(41)32-22(27(31)39)10-12-25(35)36/h1-9,15,18,22-23H,10-14,16H2,(H2,31,39)(H,32,41)(H,33,40)(H,35,36)(H,37,38)(H,42,43)/t18-,22+,23+/m1/s1

InChIKey

• InChI 1.03: RXBMEHOLQJITJI-LEOXJPRUSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N-{(2S)-3-[(S)-(4-bromophenyl)(hydroxy)phosphoryl]-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]propanoyl}-L-alpha-glutamyl-L-alpha-glutamine
• OpenEye OEToolkits 1.7.6: (4S)-5-azanyl-4-[[(2S)-2-[[(2S)-2-[[(4-bromophenyl)-oxidanyl-phosphoryl]methyl]-3-(3-phenyl-1,2-oxazol-5-yl)propanoyl]amino]-5-oxidanyl-5-oxidanylidene-pentanoyl]amino]-5-oxidanylidene-pentanoic acid

PDB entries

Showing all 1 items

PDB-4gr3:
Crystal structure of the catalytic domain of Human MMP12 in complex with selective phosphinic inhibitor RXP470A