ChemComp-R4C: N-{(2S)-3-[(R)-(4-bromophenyl)(hydroxy)phosphoryl]-2-[(3-phenyl-1...

Basic information

• Entry: Database: PDB chemical components / ID: R4C
• Name: Name: N-{(2S)-3-[(R)-(4-bromophenyl)(hydroxy)phosphoryl]-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]propanoyl}-L-alanyl-L-alaninamid; Synonyms: RXP470C

BIRD information

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

Synonyms

• RXP470C (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: 70698424

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: C₂₅H₂₈BrN₄O₆P / Number of atoms: 65 / Formula weight: 591.391 / Formal charge: 0

Others

4gr8

14E

ALA

ALA

NH2

Type: peptide-like / PDB classification: HETAIN / Three letter code: R4C / Ideal coordinates details: Corina / Model coordinates PDB-ID: 4GR8 / Subcomponent: 14E, ALA, ALA, NH2

History

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

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C(N)C(NC(=O)C(NC(=O)C(CP(=O)(O)c1ccc(Br)cc1)Cc3onc(c2ccccc2)c3)C)C
• CACTVS 3.370: C[CH](NC(=O)[CH](C)NC(=O)[CH](Cc1onc(c1)c2ccccc2)C[P](O)(=O)c3ccc(Br)cc3)C(N)=O
• OpenEye OEToolkits 1.7.6: CC(C(=O)N)NC(=O)C(C)NC(=O)C(Cc1cc(no1)c2ccccc2)CP(=O)(c3ccc(cc3)Br)O

SMILES CANONICAL

• CACTVS 3.370: C[C@H](NC(=O)[C@H](C)NC(=O)[C@H](Cc1onc(c1)c2ccccc2)C[P](O)(=O)c3ccc(Br)cc3)C(N)=O
• OpenEye OEToolkits 1.7.6: C[C@@H](C(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](Cc1cc(no1)c2ccccc2)CP(=O)(c3ccc(cc3)Br)O

InChI

• InChI 1.03: InChI=1S/C25H28BrN4O6P/c1-15(23(27)31)28-24(32)16(2)29-25(33)18(14-37(34,35)21-10-8-19(26)9-11-21)12-20-13-22(30-36-20)17-6-4-3-5-7-17/h3-11,13,15-16,18H,12,14H2,1-2H3,(H2,27,31)(H,28,32)(H,29,33)(H,34,35)/t15-,16-,18+/m0/s1

InChIKey

• InChI 1.03: HXHLWPVBBLIGJV-XYJFISCASA-N

SYSTEMATIC NAME

• ACDLabs 12.01: N-{(2S)-3-[(R)-(4-bromophenyl)(hydroxy)phosphoryl]-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]propanoyl}-L-alanyl-L-alaninamide
• OpenEye OEToolkits 1.7.6: [(2S)-3-[[(2S)-1-[[(2S)-1-azanyl-1-oxidanylidene-propan-2-yl]amino]-1-oxidanylidene-propan-2-yl]amino]-3-oxidanylidene-2-[(3-phenyl-1,2-oxazol-5-yl)methyl]propyl]-(4-bromophenyl)phosphinic acid

PDB entries

Showing all 1 items

PDB-4gr8:
Crystal structure of the catalytic domain of Human MMP12 in complex with selective phosphinic inhibitor RXP470C