Details of the Drug

General Information of Drug (ID: DMBK9PS)

Drug Name

AM-404

Synonyms

AM 404; AM-404; 183718-77-6; am404; UNII-XVJ94H0U21; 198022-70-7; CHEMBL39878; XVJ94H0U21; CPD000449274; (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide; N-(4-hydroxyphenyl)-eicosa-5,8,11,14-tetraenamide; SMR000449274; SR-01000597390; N-(4-Hydroxyphenyl)-arachidonylamide; N-(4-Hydroxyphenyl)arachidonylamide; N-(4-Hydroxyphenyl)arachidonoyl amide; NCGC00025010-01; Tocris-1116; AC1O7GXA; 5,8,11,14-Eicosatetraenamide, N-(4-hydroxyphenyl)-, (all-Z)-; N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide

Indication

Disease Entry	ICD 11	Status	REF
Discovery agent	N.A.	Investigative	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 2

Molecular Weight (mw)

395.6

Logarithm of the Partition Coefficient (xlogp)

7.2

Rotatable Bond Count (rotbonds)

15

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

2

Chemical Identifiers

Formula: C26H37NO2
IUPAC Name: (5Z,8Z,11Z,14Z)-N-(4-hydroxyphenyl)icosa-5,8,11,14-tetraenamide
Canonical SMILES: CCCCC/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCC(=O)NC1=CC=C(C=C1)O
InChI: InChI=1S/C26H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(29)27-24-20-22-25(28)23-21-24/h6-7,9-10,12-13,15-16,20-23,28H,2-5,8,11,14,17-19H2,1H3,(H,27,29)/b7-6-,10-9-,13-12-,16-15-
InChIKey: IJBZOOZRAXHERC-DOFZRALJSA-N

Cross-matching ID

PubChem CID: 6604822
CAS Number: 183718-77-6
TTD ID: D02GOH

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Cannabinoid receptor 1 (CB1)	TT6OEDT	CNR1_HUMAN	Inhibitor	[1]
Cannabinoid receptor 2 (CB2)	TTMSFAW	CNR2_HUMAN	Inhibitor	[2]
Fatty acid amide hydrolase (FAAH)	TTDP1UC	NOUNIPROTAC	Inhibitor	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Nuclear factor of activated T-cells, cytoplasmic 2 (NFATC2)	OTK5T6HZ	NFAC2_HUMAN	Gene/Protein Processing	[3]
Transient receptor potential cation channel subfamily V member 1 (TRPV1)	OTHHDR03	TRPV1_HUMAN	Gene/Protein Processing	[4]
Tumor necrosis factor (TNF)	OT4IE164	TNFA_HUMAN	Gene/Protein Processing	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Discovery agent

ICD Disease Classification

N.A.

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Cannabinoid receptor 1 (CB1)	DTT	CNR1	5.59E-02	-0.22	-0.45
Cannabinoid receptor 1 (CB1)	DTT	CNR1	7.68E-01	-0.06	-0.46

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Head group analogs of arachidonylethanolamide, the endogenous cannabinoid ligand. J Med Chem. 1996 Oct 25;39(22):4515-9.
2	New analgesics synthetically derived from the paracetamol metabolite N-(4-hydroxyphenyl)-(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-enamide. J Med Chem. 2008 Dec 25;51(24):7800-5.
3	The acetaminophen-derived bioactive N-acylphenolamine AM404 inhibits NFAT by targeting nuclear regulatory events. Biochem Pharmacol. 2007 Apr 1;73(7):1013-23. doi: 10.1016/j.bcp.2006.12.001. Epub 2006 Dec 15.
4	"TRPV1 is a component of the atrial natriuretic signaling complex, and using orally delivered antagonists, presents a valid therapeutic target in the longitudinal reversal and treatment of cardiac hypertrophy and heart failure". Channels (Austin). 2019 Dec;13(1):1-16. doi: 10.1080/19336950.2018.1547611.