Methoxy arachidonyl fluorophosphonate

Names
Preferred IUPAC name

Methyl [(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yl]phosphonofluoridate

Other names

MAFP

Identifiers

CAS Number

* 188404-10-6 N[ChemSpider]

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL113262 Y

ChemSpider |

* 8604682 Y

EC Number |

* 201-185-2

PubChem CID

* 10429254

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- Y

Key: KWKZCGMJGHHOKJ-ZKWNWVNESA-N Y

SMILES

* FP(=O)(OC)CCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC

Properties

Chemical formula

| C21H36FO2P
Molar mass | 370.5

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Y verify (what is YN ?)
Infobox references

Methoxy arachidonyl fluorophosphonate, commonly referred as MAFP, is an irreversible active site-directed enzyme inhibitor that inhibits nearly all serine hydrolases and serine proteases.[1] It inhibits phospholipase A2 and fatty acid amide hydrolase with special potency, displaying IC50 values in the low-nanomolar range. In addition, it binds to the CB1 receptor in rat brain membrane preparations (IC50 = 20 nM),[2] but does not appear to agonize or antagonize the receptor,[3] though some related derivatives do show cannabinoid-like properties.[4]

## See also

* DIFP – diisopropyl fluorophosphate, a related inhibitor
* IDFP – isopropyl dodecylfluorophosphonate, another related inhibitor with selectivity for FAAH and MAGL
* Activity-based probes

## References

1. ↑ "Selectivity of inhibitors of endocannabinoid biosynthesis evaluated by activity-based protein profiling". Bioorg. Med. Chem. Lett. 18 (22): 5838–41. July 2008. doi:10.1016/j.bmcl.2008.06.091. PMID 18657971.
2. ↑ "Methyl arachidonyl fluorophosphonate: a potent irreversible inhibitor of anandamide amidase". Biochem. Pharmacol. 53 (3): 255–60. 1997. doi:10.1016/s0006-2952(96)00830-1. PMID 9065728.
3. ↑ "An optimized approach to study endocannabinoid signaling: evidence against constitutive activity of rat brain adenosine A1 and cannabinoid CB1 receptors". Br. J. Pharmacol. 140 (8): 1451–9. 2003. doi:10.1038/sj.bjp.0705577. PMID 14623770.
4. ↑ "Cannabinoid properties of methylfluorophosphonate analogs". J Pharmacol Exp Ther 294 (3): 1209–18. Sep 2000. PMID 10945879.

* v
* t
* e

Prostanoid signaling modulators

Receptor
(ligands)|

| DP (D2)|

| DP1|

* Agonists: Prostaglandin D2
* Treprostinil

* Antagonists: Asapiprant
* Laropiprant
* Vidupiprant

|

DP2|

* Agonists: Indometacin
* Prostaglandin D2

* Antagonists: ADC-3680
* AZD-1981
* Bay U3405
* Fevipiprant
* MK-1029
* MK-7246
* QAV-680
* Ramatroban
* Setipiprant
* Timapiprant
* TM30089
* Vidupiprant

EP (E2)|

| EP1|

* Agonists: Beraprost
* Enprostil
* Iloprost (ciloprost)
* Latanoprost
* Lubiprostone
* Misoprostol
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* Sulprostone

* Antagonists: AH-6809
* ONO-8130
* SC-19220
* SC-51089
* SC-51322

|

EP2|

* Agonists: Butaprost
* Misoprostol
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* Treprostinil

* Antagonists: AH-6809
* PF-04418948
* TG 4-155

EP3|

* Agonists: Beraprost
* Carbacyclin
* Cicaprost
* Enprostil
* Iloprost (ciloprost)
* Isocarbacyclin
* Latanoprost
* Misoprostol
* Prostaglandin D2
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* Remiprostol
* Sulprostone

* Antagonists: L-798106

EP4|

* Agonists: Lubiprostone
* Misoprostol
* Prostaglandin E1 (alprostadil)
* Prostaglandin E2 (dinoprostone)
* TCS-2510

* Antagonists: Grapiprant
* GW-627368
* L-161982
* ONO-AE3-208

Unsorted|

* Agonists: 16,16-Dimethyl Prostaglandin E2
* Aganepag
* Carboprost
* Evatanepag
* Gemeprost
* Nocloprost
* Omidenepag
* Prostaglandin F2α (dinoprost)
* Simenepag
* Taprenepag

FP (F2α)|

* Agonists: Alfaprostol
* Bimatoprost
* Carboprost
* Cloprostenol
* Enprostil
* Fluprostenol
* Latanoprost
* Prostaglandin D2
* Prostaglandin F2α (dinoprost)
* Sulotroban
* Tafluprost
* Travoprost
* Unoprostone

IP (I2)|

* Agonists: ACT-333679
* AFP-07
* Beraprost
* BMY-45778
* Carbacyclin
* Cicaprost
* Iloprost (ciloprost)
* Isocarbacyclin
* MRE-269
* NS-304
* Prostacyclin (prostaglandin I2, epoprostenol)
* Prostaglandin E1 (alprostadil)
* Ralinepag
* Selexipag
* Taprostene
* TRA-418
* Treprostinil

* Antagonists: RO1138452

TP (TXA2)|

* Agonists: Carbocyclic thromboxane A2
* I-BOP
* Thromboxane A2
* U-46619
* Vapiprost

* Antagonists: 12-HETE
* 13-APA
* AA-2414
* Argatroban
* Bay U3405
* BMS-180,291
* Daltroban
* Domitroban
* EP-045
* GR-32191
* ICI-185282
* ICI-192605
* Ifetroban
* Imitrodast
* L-655240
* L-670596
* Linotroban
* Mipitroban
* ONO-3708
* ONO-11120
* Picotamide
* Pinane thromboxane A2
* Ramatroban
* Ridogrel
* S-145
* Samixogrel
* Seratrodast
* SQ-28,668
* SQ-29,548
* Sulotroban
* Terbogrel
* Terutroban
* TRA-418

Unsorted|

* Arbaprostil
* Ataprost
* Ciprostene
* Clinprost
* Cobiprostone
* Delprostenate
* Deprostil
* Dimoxaprost
* Doxaprost
* Ecraprost
* Eganoprost
* Enisoprost
* Eptaloprost
* Esuberaprost
* Etiproston
* Fenprostalene
* Flunoprost
* Froxiprost
* Lanproston
* Limaprost
* Luprostiol
* Meteneprost
* Mexiprostil
* Naxaprostene
* Nileprost
* Nocloprost
* Ornoprostil
* Oxoprostol
* Penprostene
* Pimilprost
* Piriprost
* Posaraprost
* Prostalene
* Rioprostil
* Rivenprost
* Rosaprostol
* Spiriprostil
* Tiaprost
* Tilsuprost
* Tiprostanide
* Trimoprostil
* Viprostol

Enzyme
(inhibitors)|

| COX
(PTGS)|

* Salicylic acids: Aloxiprin
* Aspirin (acetylsalicylic acid)
* Benorilate (benorylate)
* Carbasalate calcium
* Diflusinal
* Dipyrocetyl
* Ethenzamide
* Guacetisal
* Magnesium salicylate
* Mesalazine (5-aminosalicylic acid)
* Methyl salicylate
* Salacetamide
* Salicin
* Salicylamide
* Salicylate (salicylic acid)
* Salsalate
* Sodium salicylate
* Triflusal; Acetic acids: Aceclofenac
* Acemetacin
* Aclofenac
* Amfenac
* Alclofenac
* Bendazac
* Bromfenac
* Bufexamac
* Bumadizone
* Cinmetacin
* Clometacin
* Diclofenac
* Difenpiramide
* Etodolac
* Felbinac
* Fenclofenac
* Fentiazac
* Glucametacin
* Indometacin (indomethacin)
* Indometacin farnesil
* Ketorolac
* Lonazolac
* Mofezolac
* Nabumetone
* Oxametacin
* Oxindanac
* Proglumetacin
* Sulindac
* Sulindac sulfide
* Tolmetin
* Zidometacin
* Zomepirac; Propionic acids: Alminoprofen
* Benoxaprofen
* Bucloxic acid (blucloxate)
* Butibufen
* Carprofen
* Dexibuprofen
* Dexindoprofen
* Dexketoprofen
* Fenbufen
* Fenoprofen
* Flunoxaprofen
* Flurbiprofen
* Ibuprofen
* Ibuproxam
* Indoprofen
* Ketoprofen
* Loxoprofen
* Miroprofen
* Naproxen
* Naproxcinod
* Oxaprozin
* Pirprofen
* Pranoprofen
* Suprofen
* Tarenflurbil
* Tepoxalin
* Tiaprofenic acid (tiaprofenate)
* Vedaprofen; Anthranilic acids (fenamic acids): Etofenamic acid (etofenamate)
* Floctafenic acid (floctafenate)
* Flufenamic acid (flufenamate)
* Meclofenamic acid (meclofenamate)
* Mefenamic acid (mefenamate)
* Morniflumic acid (morniflumate)
* Niflumic acid (niflumate)
* Talinflumic acid (talinflumate)
* Tolfenamic acid (tolfenamate); Pyrazolones: Azapropazone
* Dipyrone
* Isopyrin
* Oxyphenbutazone
* Phenylbutazone; Enolic acids (oxicams): Ampiroxicam
* Droxicam
* Enolicam
* Isoxicam
* Lornoxicam
* Meloxicam
* Piroxicam
* Tenoxicam; 4-Aminoquinolines: Antrafenine
* Floctafenine
* Glafenine; Quinazolines: Fluproquazone
* Proquazone; Aminonicotinic acids: Clonixeril
* Clonixin
* Flunixin; Sulfonanilides: Flosulide
* Nimesulide; Aminophenols (anilines): Acetanilide
* AM-404 (N-arachidonoylaminophenol)
* Bucetin
* Paracetamol (acetaminophen)
* Parapropamol
* Phenacetin
* Propacetamol; Selective COX-2 inhibitors (coxibs): Apricoxib
* Celecoxib
* Cimicoxib
* Deracoxib
* Etoricoxib
* Firocoxib
* Lumiracoxib
* Mavacoxib
* Parecoxib
* Polmacoxib
* Robenacoxib
* Rofecoxib
* Tilmacoxib
* Valdecoxib; Others/unsorted: Anitrazafen
* Clobuzarit
* Curcumin
* DuP-697
* FK-3311
* Flumizole
* FR-122047
* Glimepiride
* Hyperforin
* Itazigrel
* L-655240
* L-670596
* Licofelone
* Menatetrenone (vitamin K2)
* NCX-466
* NCX-4040
* NS-398
* Pamicogrel
* Resveratrol
* Romazarit
* Rosmarinic acid
* Rutecarpine
* Satigrel
* SC-236
* SC-560
* SC-58125
* Tenidap
* Tiflamizole
* Timegadine
* Trifenagrel
* Tropesin

|

PGD2S|

* Retinoids
* Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)

PGES|

HQL-79

PGFS|

Bimatoprost

PGI2S|

Tranylcypromine

TXAS|

* Camonagrel
* Dazmegrel
* Dazoxiben
* Furegrelate
* Isbogrel
* Midazogrel
* Nafagrel
* Nicogrelate
* Ozagrel
* Picotamide
* Pirmagrel
* Ridogrel
* Rolafagrel
* Samixogrel
* Terbogrel
* U63557A

Others|

* Precursors: Linoleic acid
* γ-Linolenic acid (gamolenic acid)
* Dihomo-γ-linolenic acid
* Diacylglycerol
* Arachidonic acid
* Prostaglandin G2
* Prostaglandin H2

See also
Receptor/signaling modulators
Leukotriene signaling modulators
Nuclear receptor modulators

* v
* t
* e

Leukotriene signaling modulators

Receptor
(ligands)|

| BLT|

| BLT1|

* Agonists: 12-HETE
* 20-Hydroxy-LTB4
* Leukotriene B4
* LY-255283

* Antagonists: 20-Carboxy-LTB4
* Amelubant
* CGS-23131 (LY-223982)
* CGS-25019C
* CP-105696
* CP-195543
* Etalocib
* LY-293111
* Moxilubant
* ONO-4057
* RG-14893
* RP-69698
* SB-209247
* SC-53228
* Ticolubant
* U-75302
* ZK-158252

|

BLT2|

* Agonists: 12-HETE
* 12-HHT
* 12-HpETE
* 15-HETE
* 15-HpETE
* 20-Hydroxy-LTB4
* Leukotriene B4

* Antagonists: CP-195543
* LY-255283
* ZK-158252

CysLT|

| CysLT1|

* Agonists: Leukotriene C4
* Leukotriene D4
* Leukotriene E4

* Antagonists: Ablukast
* BAYu9773
* BAYu9916
* BAYx7195
* Cinalukast
* FPL-55712
* ICI-198615
* Iralukast
* LY-170680
* Masilukast
* MK-571
* Montelukast
* ONO-1078
* Pobilukast
* Pranlukast
* Ritolukast
* SKF-104353
* SR-2640
* Sulukast
* Tipelukast
* Tomelukast
* Verlukast
* Zafirlukast
* ZD-3523

|

CysLT2|

* Agonists: Leukotriene C4
* Leukotriene D4
* Leukotriene E4

* Antagonists: BAYu9773
* BAYu9916

CysLTE|

* Agonists: Leukotriene E4

Enzyme
(inhibitors)|

| 5-LOX|

* 2-TEDC
* Baicalein
* BW-A4C
* BW-B70C
* Caffeic acid
* CDC
* CJ-13610
* Curcumin
* Fenleuton
* Hyperforin
* Hypericum perforatum (St. John's Wort)
* Meclofenamic acid (meclofenamate)
* Minocycline
* N-Stearoyldopamine
* Timegadine
* Zileuton

* FLAP inhibitors: AM-103
* AM-679
* BAYx1005
* MK-591
* MK-886

|

12-LOX|

* 2-TEDC
* 3-Methoxytropolone
* Baicalein
* CDC

15-LOX|

* 2-TEDC
* CDC
* Luteolin
* PD-146176

LTA4H|

* Acebilustat
* Captopril
* DG-051
* Fosinoprilat
* JNJ-26993135
* SA-6541
* SC-57461A
* Ubenimex (bestatin)

LTB4H|

* 17-Octadecynoic acid

LTC4S|

* Azelastine
* MK-886

LTC4H|

* Acivicin
* Serine-borate complex

LTD4|

* Cilastatin
* Ubenimex (bestatin)

Others|

* Precursors: Linoleic acid
* γ-Linolenic acid (gamolenic acid)
* Dihomo-γ-linolenic acid
* Diacylglycerol
* Arachidonic acid
* 5-HPETE (arachidonic acid 5-hydroperoxide)
* Leukotriene A4

See also
Receptor/signaling modulators
Prostanoid signaling modulators
Nuclear receptor modulators

* v
* t
* e

Cannabinoid receptor modulators

Receptor
(ligands)</small>|

| CB1|

* Agonists (abridged; see here for more): 2-AG
* 2-AGE (noladin ether)
* 11-Hydroxy-THC
* α-Amyrin · β-Amyrin
* AB-CHMINACA
* AM-1172
* AM-1220
* AM-1221
* AM-1235
* AM-2201
* AM-2232
* Anandamide
* Arvanil
* AZ-11713908
* Cannabinol
* CB-13
* CP 47,497
* CP 55,940
* Dimethylheptylpyran
* DEA
* ECG
* EGCG
* Epicatechin
* Gallocatechol (gallocatechin)
* Honokiol
* HU-210
* JWH-007
* JWH-015
* JWH-018
* JWH-073
* Kavain
* L-759,633
* Levonantradol
* Menabitan
* Nabilone
* Nabitan
* NADA
* O-1812
* Oleamide
* Pravadoline
* Serinolamide A
* THC (dronabinol)
* UR-144
* WIN 55,212-2
* Yangonin

* Antagonists: AM-251
* AM-6545
* Cannabidiol
* Cannabigerol
* Drinabant
* Falcarinol (carotatoxin)
* Hemopressin
* Ibipinabant
* LY-320,135
* MK-9470
* NESS-0327
* O-2050
* Otenabant
* PF-514273
* PipISB
* Rimonabant
* Rosonabant
* Surinabant
* Taranabant
* THCV
* TM-38837
* VCHSR
* Virodhamine

* Antibodies: Brizantin (Бризантин)
* Dietressa (Диетресса)

* Unknown/unsorted: MAFP

|

CB2|

* Agonists: 2-AG
* 2-AGE (noladin ether)
* 3,3'-Diindolylmethane
* 4-O-Methylhonokiol
* α-Amyrin · β-Amyrin
* A-796,260
* A-834,735
* A-836,339
* AM-1172
* AM-1221
* AM-1235
* AM-1241
* AM-2232
* Anandamide
* AZ-11713908
* Cannabinol
* Caryophyllene
* CB-13
* CBS-0550
* CP 55,940
* GW-405,833 (L-768,242)
* GW-842,166X
* HU-308
* JTE 7-31
* JWH-007
* JWH-015
* JWH-018
* JWH-73
* JWH-133
* L-759,633
* L-759,656
* Lenabasum (anabasum)
* Magnolol
* MDA-19
* Nabitan
* NADA
* Olorinab (APD-371)
* PF-03550096
* S-444,823
* SER-601
* Serinolamide A
* UR-144
* Tedalinab
* THC (dronabinol)
* THCV
* Tetrahydromagnolol
* Virodhamine

* Antagonists: 4-O-Methylhonokiol
* AM-630
* BML-190
* Cannabidiol
* Honokiol
* JTE-907
* SR-144,528
* WIN 54,461
* WIN 56,098

NAGly
(GPR18)|

* Agonists: Abnormal cannabidiol
* ACPA
* AM251
* Anandamide
* Cannabidiol
* NADGly
* THC (dronabinol)
* O-1602

* Antagonists: CID-85469571
* O-1918

GPR55|

* Agonists: 2-AGE (noladin ether)
* 2-ALPI
* Abnormal cannabidiol
* AM-251
* CID1011163
* CID1252842
* CID1792579
* CP 55,940
* GSK-494581A
* Lysophosphatidylinositol
* ML-184
* ML-185
* ML-186
* O-1602
* Oleoylethanolamide
* Palmitoylethanolamide
* THC (dronabinol)

* Antagonists: Cannabidiol
* CID-16020046
* ML-191
* ML-192
* ML-193
* O-1918
* PSB-SB-487
* PSB-SB-1202
* PSB-SB-1203
* Tetrahydromagnolol

GPR119|

* Agonists: 2-Oleoylglycerol
* Anandamide
* APD668
* AR-231,453
* AS-1269574
* MBX-2982
* N-Oleoyldopamine
* Oleoylethanolamide
* Olvanil
* PSN-375,963
* PSN-632,408

Unsorted|

* Agonists: Revosimeline

Transporter
(modulators)|

| eCBTs|

* Inhibitors: 5'-DMH-CBD
* AM-404
* AM-1172
* Arachidonoyl serotonin
* Arvanil
* Cannabidiol
* Guineensine
* LY-2183240
* O-2093
* OMDM-2
* Paracetamol (acetaminophen)
* SB-FI-26
* UCM-707
* URB-597
* VDM-11
* WOBE490
* WOBE491
* WOBE492

|

Enzyme
(modulators)|

| FAAH|

* Inhibitors: 4-Nonylphenylboronic acid
* AACOCF3
* AM-404
* Arachidonoyl serotonin
* BIA 10-2474
* Biochanin A
* Genistein
* IDFP
* JNJ-1661010
* JNJ-42165279
* JZL-195
* Kaempferol
* LY-2183240
* MAFP
* Palmitoylisopropylamide
* Paracetamol (acetaminophen)
* PF-3845
* PF-04457845
* PF-750
* SA-47
* SA-57
* TAK 21d
* TC-F 2
* UCM710
* URB-597

* Activators: PDP-EA

|

MAGL|

* Inhibitors: ABX-1431
* IDFP
* JJKK 048
* JW 642
* JZL-184
* JZL-195
* JZP-361
* KML 29
* MAFP
* MJN110
* NAM
* Pristimerin
* URB-602

ABHD6|

* Inhibitors: JZP-169
* JZP-430
* KT182
* KT185
* KT195
* KT203
* LEI-106
* ML294
* ML295
* ML296
* UCM710
* WWL-70

ABHD12|

* Inhibitors: Betulinic acid
* Maslinic acid
* MAFP
* Oleanolic acid
* Orlistat (tetrahydrolipstatin)
* Ursolic acid

Others|

* Precursors: Phosphatidylethanolamine
* NAPE
* Diacylglycerol

* Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor)
* ARN-272 (FAAH-like anandamide transporter inhibitor)

See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)

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Original source: https://en.wikipedia.org/wiki/Methoxy arachidonyl fluorophosphonate. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Methoxy_arachidonyl_fluorophosphonate&oldid=4175755"
*[CID]: Compound ID
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[DP (D2)]: Prostaglandin D2 receptor
*[DP1]: Prostaglandin D2 receptor 1
*[DP2]: Prostaglandin D2 receptor 2
*[EP (E2)]: Prostaglandin E2 receptor
*[EP1]: Prostaglandin EP1 receptor
*[EP2]: Prostaglandin EP2 receptor
*[EP3]: Prostaglandin EP3 receptor
*[EP4]: Prostaglandin EP4 receptor
*[FP (F2α)]: Prostaglandin F receptor
*[IP (I2)]: Prostacyclin receptor
*[TP (TXA2)]: Thromboxane receptor
*[COX]: Cyclooxygenase
*[PTGS]: prostaglandin G/H synthase
*[PGD2S]: Prostaglandin D synthase
*[PGES]: Prostaglandin E synthase
*[PGFS]: Prostaglandin F synthase
*[PGI2S]: Prostacyclin synthase
*[TXAS]: Thromboxane A synthase
*[BLT]: Leukotriene B4 receptor
*[BLT1]: Leukotriene B4 receptor 1
*[BLT2]: Leukotriene B4 receptor 2
*[CysLT]: Cysteinyl leukotriene receptor
*[CysLT1]: Cysteinyl leukotriene receptor 1
*[CysLT2]: Cysteinyl leukotriene receptor 2
*[CysLTE]: Cysteinyl leukotriene receptor E
*[5-LOX]: Arachidonate 5-lipoxygenase
*[FLAP]: Arachidonate 5-lipoxygenase-activating protein
*[12-LOX]: Arachidonate 12-lipoxygenase
*[15-LOX]: Arachidonate 15-lipoxygenase
*[LTA4H]: Leukotriene A4 hydrolase
*[LTB4H]: Leukotriene B4 ω-hydroxylase
*[LTC4S]: Leukotriene C4 synthase
*[LTC4H]: Leukotriene C4 hydrolase
*[LTD4]: Leukotriene D4 hydrolase
*[CB1]: Cannabinoid receptor type 1
*[CB2]: Cannabinoid receptor type 2
*[NAGly]: N-Arachidonyl glycine receptor
*[GPR18]: G protein-coupled receptor 18
*[GPR55]: G protein-coupled receptor 55
*[GPR119]: G protein-coupled receptor 119
*[eCBTs]: Endocannabinoid transporter
*[FAAH]: Fatty acid amide hydrolase
*[ABHD6]: alpha/beta-Hydrolase domain containing 6
*[ABHD12]: alpha/beta-Hydrolase domain containing 12