Basic information
- CAS
59880-97-6- Standard SMILES
CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccccc1)C(=O)O- InChIKey
PRQROPMIIGLWRP-BZSNNMDCSA-N- Molecular formula
- C21H31N3O5S
- Average molar mass
- 437.6 g/mol
- Monoisotopic mass
- 437.19844209
Overview
N-formyl-L-methionyl-L-leucyl-L-phenylalanine is a tripeptide composed of L-Met, L-Leu and L-Phe in a linear sequence with a formyl group at the amino terminus. It acts as a potent inducer of leucocyte chemotaxis and macrophage activator as well as a ligand for the FPR receptor. It is functionally related to a L-leucine, a N-formyl-L-methionine and a L-phenylalanine. It is a conjugate acid of a N-formyl-L-methionyl-L-leucyl-L-phenylalaninate.
Names & identifiers
- Preferred name
- N-Formyl-L-methionyl-L-leucyl-L-phenylalanine
- IUPAC
- (2S)-2-[[(2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoic acid
- English name
- Tyramine hydrochloride
- Molecular formula
- C21H31N3O5S
- Molecular weight
- 437.55
Names & synonyms
59880-97-6fMetLeuPheN-Formyl-L-methionyl-L-leucyl-L-phenylalanineDTXSID9041077CHEBI:53490RefChem:1091810DTXCID00820624N-Formyl-Met-Leu-PheFMLPfMLFN-Formyl-methionyl-leucyl-phenylalaninefMet-Leu-Phe
Show more names
TYRAMINE HCLfMLF, fMLPNSC 350593TYROSAMINE HCLTYRAMINE HCL(P)TYRAMINE HCL(RG)TIMTEC-BB SBB003808N-Formyl-Met-Leu-Phe-OH
Chemotactic peptideF-Met-leu-pheformyl-Met-Leu-PheMFCD00036780(S)-2-((S)-2-((S)-2-Formamido-4-(methylthio)butanamido)-4-methylpentanamido)-3-phenylpropanoic acidFor-Met-Leu-Phe-OHMLS002207097CHEMBL267179
Database identifiers
- CAS
59880-97-6- PubChem CID
- 443295
- DTXSID
DTXSID9041077- ChEMBL
CHEMBL267179
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 150 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 13
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 567
Physicochemical properties
- Melting point
- 271 · 271-274 °C(lit.)
- Boiling point
- 269 °C · 269 °C
- Density
- 1.198 · 1.198±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 50 mg/mL, · DMF: 50 mg/mL, clear, colorless
- pka
- 3.5 · 3.50±0.10(Predicted)
- form
- White to off-white lyophilized solid
- color
- White to Almost white
- BRN
- 2315783 · 2315783
- Sequence
- N-Formyl-Met-Leu-Phe-OH
- Major Application
- cell analysis
- InChIKey
- PRQROPMIIGLWRP-BZSNNMDCSA-N
- SMILES
- C(O)(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCSC)NC=O
- CAS DataBase Reference
- 59880 · 59880-97-6(CAS DataBase Reference)
- FDA UNII
- 6 AVJ8RCE · LO6AVJ8RCE
- UNSPSC Code
Safety & regulation
Safety data
- F
- 3-10
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- SJ6050000
- hs_code
- 2930.90.9250
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 26-36-22
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesInduces leucocyte chemotaxis, and activates macrophages
UsesN-Formyl-Met-Leu-Phe has been used for:creating gradients in Zigmond chamber chemotaxis assay performed on neutrophilsuse in neutrophil chemotaix assay anddetermination of the involvement of MAPK-activating protein kinase-2 (MAPKAPK-2) and/or p38, in the signaling pathway of human polymorphonuclear leukocytes (PMNs) stimulated by N-Formyl-Met-Leu-Phe.
General DescriptionN-Formyl-Met-Leu-Phe is a chemotactin peptide, which functions on polymorphonuclear leukocytes (PMN), neutrophils etc.
Suppliers99 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]
上海莉凯化工技术有限公司16628776521 · [email protected]
上海哲研生物科技有限公司021-18017610038 18017610038 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海优宁维生物科技股份有限公司15921930842 15921930842 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
南京昱盛康生物科技有限公司13327808530 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
Related reactions
2 records
Compound notes
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