N-Formyl-Met-Leu-Phe
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Basic Info
| Common Name | N-Formyl-Met-Leu-Phe(F00951) |
| 2D Structure | |
| FRCD ID | F00951 |
| CAS Number | 59880-97-6 |
| PubChem CID | 443295 |
| Formula | C21H31N3O5S |
| IUPAC Name | (2S)-2-[[(2S)-2-[[(2S)-2-formamido-4-methylsulfanylbutanoyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoic acid |
| InChI Key | PRQROPMIIGLWRP-BZSNNMDCSA-N |
| InChI | InChI=1S/C21H31N3O5S/c1-14(2)11-17(23-19(26)16(22-13-25)9-10-30-3)20(27)24-18(21(28)29)12-15-7-5-4-6-8-15/h4-8,13-14,16-18H,9-12H2,1-3H3,(H,22,25)(H,23,26)(H,24,27)(H,28,29)/t16-,17-,18-/m0/s1 |
| Canonical SMILES | CC(C)CC(C(=O)NC(CC1=CC=CC=C1)C(=O)O)NC(=O)C(CCSC)NC=O |
| Isomeric SMILES | CC(C)C[C@@H](C(=O)N[C@@H](CC1=CC=CC=C1)C(=O)O)NC(=O)[C@H](CCSC)NC=O |
| Synonyms |
N-Formyl-Met-Leu-Phe
59880-97-6
FMLP
Chemotactic peptide
F-Met-leu-phe
fMLF
fMetLeuPhe
fMet-Leu-Phe
N-Formyl-L-methionyl-L-leucyl-L-phenylalanine
N-Formyl-methionyl-leucyl-phenylalanine
|
| Classifies |
Predicted: Veterinary Drug
|
| Update Date | Nov 13, 2018 16:49 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Amino acids, peptides, and analogues |
| Intermediate Tree Nodes | Peptides |
| Direct Parent | Oligopeptides |
| Alternative Parents |
|
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Alpha-oligopeptide - Phenylalanine or derivatives - Leucine or derivatives - Methionine or derivatives - N-acyl-alpha-amino acid - N-acyl-l-alpha-amino acid - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - N-formyl-alpha-amino acid - N-formyl-alpha amino acid or derivatives - 3-phenylpropanoic-acid - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - Monocyclic benzene moiety - Fatty amide - N-acyl-amine - Fatty acyl - Benzenoid - Secondary carboxylic acid amide - Carboxamide group - Thioether - Dialkylthioether - Sulfenyl compound - Carboxylic acid - Monocarboxylic acid or derivatives - Organonitrogen compound - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Carbonyl group - Organic nitrogen compound - Organooxygen compound - Organosulfur compound - Organic oxide - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 437.555 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 13 |
| Complexity | 567 |
| Monoisotopic Mass | 437.198 |
| Exact Mass | 437.198 |
| XLogP | 1.5 |
| Formal Charge | 0 |
| Heavy Atom Count | 30 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.5121 |
| Human Intestinal Absorption | HIA+ | 0.8141 |
| Caco-2 Permeability | Caco2- | 0.6784 |
| P-glycoprotein Substrate | Substrate | 0.7294 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8757 |
| Non-inhibitor | 0.9851 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9421 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.7302 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.7688 |
| CYP450 2D6 Substrate | Non-substrate | 0.7995 |
| CYP450 3A4 Substrate | Non-substrate | 0.5085 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9253 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.8557 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9502 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.7421 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8759 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9890 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9935 |
| Non-inhibitor | 0.9656 | |
| AMES Toxicity | Non AMES toxic | 0.9175 |
| Carcinogens | Non-carcinogens | 0.9465 |
| Fish Toxicity | High FHMT | 0.9395 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9155 |
| Honey Bee Toxicity | Low HBT | 0.7751 |
| Biodegradation | Not ready biodegradable | 0.8897 |
| Acute Oral Toxicity | III | 0.6932 |
| Carcinogenicity (Three-class) | Non-required | 0.7627 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.5127 | LogS |
| Caco-2 Permeability | 0.6915 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.9856 | LD50, mol/kg |
| Fish Toxicity | 1.6568 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.2875 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Nortriterpene lactones from the fruits of Schisandra arisanensis. | J Nat Prod | 2010 Jul 23 | 20536188 |
| Olive oil-based lipid emulsion's neutral effects on neutrophil functions andleukocyte-endothelial cell interactions. | JPEN J Parenter Enteral Nutr | 2006 Jul-Aug | 16804125 |
| Synthesis of phosphatidylinositol 3,4,5-trisphosphate in permeabilized neutrophils regulated by receptors and G-proteins. | J Biol Chem | 1993 Aug 15 | 8394332 |
| Effect of pectin on formyl methionyl-leucyl-phenylalanine (FMLP)-injuredintestinal mucosa of rat. | J Nutr Sci Vitaminol (Tokyo) | 1992 Apr | 1324298 |
| Effect of dietary alpha-linolenate on platelet-activating factor production inrat peritoneal polymorphonuclear leukocytes. | J Immunol | 1991 Sep 1 | 1679081 |
| Dietary linoleate supplementation modulates formyl-peptide receptor expressionand functional responses of rat neutrophils. | J Lab Clin Med | 1990 Apr | 2157784 |