Explore a selection of our essential drug information below, or:
Overview
- DrugBank ID
- DB02465
- Type
- Small Molecule
- Clinical Trials
- Phase 0
- 0
- Phase 1
- 0
- Phase 2
- 0
- Phase 3
- 0
- Phase 4
- 0
Identification
- Generic Name
- Methoxy arachidonyl fluorophosphonate
- DrugBank Accession Number
- DB02465
- Background
Methoxy arachidonyl fluorophosphonate, commonly referred as MAFP, is an irreversible active site-directed enzyme inhibitor that inhibits nearly all serine hydrolases and serine proteases. It inhibits phospholipase A2 and fatty acid amide hydrolase with special potency, displaying IC50 values in the low-nanomolar range.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Methoxy arachidonyl fluorophosphonate (DB02465)
- Weight
- Average: 370.4815
Monoisotopic: 370.243695113 - Chemical Formula
- C21H36FO2P
- Synonyms
- MAFP
- Methoxy arachidonyl fluorophosphonate
- Methyl arachidonylfluorophosphonate
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism UFatty-acid amide hydrolase 1 Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phosphonic acid esters. These are organic compounds containing phosphonic acid ester functional group, with the general structure ROP(=O)OH (R = organyl group).
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Organic phosphonic acids and derivatives
- Sub Class
- Phosphonic acid esters
- Direct Parent
- Phosphonic acid esters
- Alternative Parents
- Alkylphosphonofluoridic acids and esters / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Alkylphosphonofluoridic acid or ester derivatives / Hydrocarbon derivative / Organic oxide / Organic oxygen compound / Organooxygen compound / Organophosphorus compound / Phosphonic acid ester
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 180509-15-3
- InChI Key
- KWKZCGMJGHHOKJ-WTIHWRCNSA-N
- InChI
- InChI=1S/C21H36FO2P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25(22,23)24-2/h7-8,10-11,13-14,16-17H,3-6,9,12,15,18-21H2,1-2H3/b8-7-,11-10-,14-13-,17-16-/t25-/m0/s1
- IUPAC Name
- (S)-(methyl [(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yl]phosphonofluoridate)
- SMILES
- [H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCC[P@](F)(=O)OC
References
- General References
- Not Available
- External Links
- PubChem Compound
- 92536013
- PubChem Substance
- 46504573
- ChemSpider
- 59053894
- ZINC
- ZINC000017654246
- PDBe Ligand
- MAY
- Wikipedia
- Methoxy_arachidonyl_fluorophosphonate
- PDB Entries
- 1mt5 / 4pkb / 4x95 / 4x97
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00038 mg/mL ALOGPS logP 6.87 ALOGPS logP 6.83 Chemaxon logS -6 ALOGPS pKa (Strongest Basic) -8.5 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 26.3 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 112.68 m3·mol-1 Chemaxon Polarizability 42.22 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9894 Caco-2 permeable + 0.5475 P-glycoprotein substrate Non-substrate 0.7119 P-glycoprotein inhibitor I Non-inhibitor 0.686 P-glycoprotein inhibitor II Non-inhibitor 0.8325 Renal organic cation transporter Non-inhibitor 0.9005 CYP450 2C9 substrate Non-substrate 0.8447 CYP450 2D6 substrate Non-substrate 0.8093 CYP450 3A4 substrate Non-substrate 0.5 CYP450 1A2 substrate Non-inhibitor 0.634 CYP450 2C9 inhibitor Non-inhibitor 0.8319 CYP450 2D6 inhibitor Non-inhibitor 0.8854 CYP450 2C19 inhibitor Non-inhibitor 0.7327 CYP450 3A4 inhibitor Non-inhibitor 0.9178 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8746 Ames test Non AMES toxic 0.7895 Carcinogenicity Carcinogens 0.668 Biodegradation Not ready biodegradable 0.834 Rat acute toxicity 3.2803 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7868 hERG inhibition (predictor II) Non-inhibitor 0.6452
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-052r-7695000000-fd8c9eea97fe8660e469 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00di-2459000000-0e889a621afd259d58d6 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009000000-cec3803c7806765b4270 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0009000000-d7c4deb0e0f1157a306a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0aba-7894000000-0cc57ed1fbb48bf6444c Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05mn-7339000000-406673746a60f67b87cb Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9720000000-25b137384d6353d753f7 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 214.03758 predictedDeepCCS 1.0 (2019) [M+H]+ 215.86247 predictedDeepCCS 1.0 (2019) [M+Na]+ 221.4683 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Catalyzes the hydrolysis of endogenous amidated lipids like the sleep-inducing lipid oleamide ((9Z)-octadecenamide), the endocannabinoid anandamide (N-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-ethanolamine), as well as other fatty amides, to their corresponding fatty acids, thereby regulating the signaling functions of these molecules (PubMed:17015445, PubMed:19926788, PubMed:9122178). Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates (PubMed:17015445, PubMed:9122178). It can also catalyze the hydrolysis of the endocannabinoid 2-arachidonoylglycerol (2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-glycerol) (PubMed:21049984). FAAH cooperates with PM20D1 in the hydrolysis of amino acid-conjugated fatty acids such as N-fatty acyl glycine and N-fatty acyl-L-serine, thereby acting as a physiological regulator of specific subsets of intracellular, but not of extracellular, N-fatty acyl amino acids (By similarity)
- Specific Function
- acylglycerol lipase activity
- Gene Name
- FAAH
- Uniprot ID
- O00519
- Uniprot Name
- Fatty-acid amide hydrolase 1
- Molecular Weight
- 63065.28 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at July 02, 2020 13:17