Details of the Drug

General Information of Drug (ID: DMC4IUQ)

Drug Name

5-(N,N-hexamethylene)-amiloride

Synonyms

5-(N,N-Hexamethylene)amiloride; Hexamethyleneamiloride; 1428-95-1; Hexamethylene amiloride; HMA-5; HMA; C12H18ClN7O; 3-Amino-6-chloro-5-(1-homopiperidyl)-N-(diaminomethylene)pyrazinecarboxamide; N,N-HEXAMETHYLENEAMILORIDE; CHEBI:76400; 3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylene)pyrazine-2-carboxamide; 3-Amino-N-(aminoiminomethyl)-6-chloro-5-(hexahydro-1H-azepin-1-yl)pyrazinecarboxamide; Pyrazinecarboxamide, 3-amino-N-(aminoiminomethyl)-6-chloro-5-(hexahydro-1H-azepin-1-yl)-; 5-HMA; Spectrum_001596

Indication

Disease Entry	ICD 11	Status	REF
Coronavirus infection	1D92	Preclinical	[1]
------------------------------------------------------------------------------------

Drug Type

Small molecular drug

Structure

3D MOL is unavailable

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

311.77

Logarithm of the Partition Coefficient (xlogp)

1.3

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

5

Chemical Identifiers

Formula: C12H18ClN7O
IUPAC Name: 3-amino-5-(azepan-1-yl)-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
Canonical SMILES: C1CCCN(CC1)C2=NC(=C(N=C2Cl)C(=O)N=C(N)N)N
InChI: InChI=1S/C12H18ClN7O/c13-8-10(20-5-3-1-2-4-6-20)18-9(14)7(17-8)11(21)19-12(15)16/h1-6H2,(H2,14,18)(H4,15,16,19,21)
InChIKey: RQQJJXVETXFINY-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 1794
ChEBI ID: CHEBI:76400
CAS Number: 1428-95-1
TTD ID: D02YIW
VARIDT ID: DR00899

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adrenergic receptor alpha-2C (ADRA2C)	TT2NUT5	ADA2C_HUMAN	Modulator (allosteric modulator)	[2]
Gonadotropin-releasing hormone receptor (GNRHR)	TT8R70G	GNRHR_HUMAN	Modulator (allosteric modulator)	[3]

------------------------------------------------------------------------------------

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
DNA damage-inducible transcript 3 protein (DDIT3)	OTI8YKKE	DDIT3_HUMAN	Gene/Protein Processing	[4]
Endoplasmic reticulum chaperone BiP (HSPA5)	OTFUIRAO	BIP_HUMAN	Gene/Protein Processing	[4]
Endoplasmin (HSP90B1)	OT02XLBR	ENPL_HUMAN	Gene/Protein Processing	[4]
Prostaglandin G/H synthase 2 (PTGS2)	OT75U9M4	PGH2_HUMAN	Gene/Protein Processing	[4]
Protein phosphatase 1 regulatory subunit 15A (PPP1R15A)	OTYG179K	PR15A_HUMAN	Gene/Protein Processing	[4]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Coronavirus infection

ICD Disease Classification

1D92

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Adrenergic receptor alpha-2C (ADRA2C)	DTT	ADRA2C	1.76E-01	-0.06	-0.28

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	Coronaviruses - drug discovery and therapeutic options. Nat Rev Drug Discov. 2016 May;15(5):327-47.
2	Characterization of the allosteric interactions between antagonists and amiloride analogues at the human alpha2A-adrenergic receptor. Mol Pharmacol. 1998 May;53(5):916-25.
3	Amiloride derivatives and a nonpeptidic antagonist bind at two distinct allosteric sites in the human gonadotropin-releasing hormone receptor. Mol Pharmacol. 2008 Jun;73(6):1808-15.
4	Amiloride derivatives induce apoptosis by depleting ER Ca(2+) stores in vascular endothelial cells. Br J Pharmacol. 2009 Apr;156(8):1296-304.