NAV

Methoxy arachidonyl fluorophosphonate

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
Similar Structures
Weight
Average: 370.4815
Monoisotopic: 370.243695113
Chemical Formula
C21H36FO2P
Synonyms
  • MAFP
  • Methoxy arachidonyl fluorophosphonate
  • Methyl arachidonylfluorophosphonate
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UFatty-acid amide hydrolase 1Not AvailableHumans
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
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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
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
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.00038 mg/mLALOGPS
logP6.87ALOGPS
logP6.83Chemaxon
logS-6ALOGPS
pKa (Strongest Basic)-8.5Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area26.3 Å2Chemaxon
Rotatable Bond Count16Chemaxon
Refractivity112.68 m3·mol-1Chemaxon
Polarizability42.22 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9894
Caco-2 permeable+0.5475
P-glycoprotein substrateNon-substrate0.7119
P-glycoprotein inhibitor INon-inhibitor0.686
P-glycoprotein inhibitor IINon-inhibitor0.8325
Renal organic cation transporterNon-inhibitor0.9005
CYP450 2C9 substrateNon-substrate0.8447
CYP450 2D6 substrateNon-substrate0.8093
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.634
CYP450 2C9 inhibitorNon-inhibitor0.8319
CYP450 2D6 inhibitorNon-inhibitor0.8854
CYP450 2C19 inhibitorNon-inhibitor0.7327
CYP450 3A4 inhibitorNon-inhibitor0.9178
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8746
Ames testNon AMES toxic0.7895
CarcinogenicityCarcinogens 0.668
BiodegradationNot ready biodegradable0.834
Rat acute toxicity3.2803 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7868
hERG inhibition (predictor II)Non-inhibitor0.6452
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-052r-7695000000-fd8c9eea97fe8660e469
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2459000000-0e889a621afd259d58d6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-cec3803c7806765b4270
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-d7c4deb0e0f1157a306a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aba-7894000000-0cc57ed1fbb48bf6444c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05mn-7339000000-406673746a60f67b87cb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-9720000000-25b137384d6353d753f7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-214.03758
predicted
DeepCCS 1.0 (2019)
[M+H]+215.86247
predicted
DeepCCS 1.0 (2019)
[M+Na]+221.4683
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Fatty-acid amide hydrolase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Fatty acid amide hydrolase activity
Specific Function
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of t...
Gene Name
FAAH
Uniprot ID
O00519
Uniprot Name
Fatty-acid amide hydrolase 1
Molecular Weight
63065.28 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. 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]
  3. 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