Details of the Drug

General Information of Drug (ID: DMXULGK)

Drug Name

Neplanocin A

Synonyms

72877-50-0; NPC-A; A-11079-B1B; NEOPLANOCIN A; (1s,2r,5r)-5-(6-amino-9h-purin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol; NSC 316458; CHEMBL8771; (-)-9-(trans-2,trans-3-Dihydroxy-4-(hydroxymethyl)-cyclopent-4-enyl)-adenine; 4-Cyclopentene-1,2-diol, 3-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)-, (1S,2R,3R)-; (1S,2R,5R)-5-(6-aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol; Nephanocin A; AC1Q4VG9; AC1L2J1E; SCHEMBL10469277; CTK5D6979; MolPort-044-561-069; ZINC3832328; BDBM50006222; CCG-208688; DIBRT

Indication

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

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

263.25

Topological Polar Surface Area (xlogp)

-2

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

4

Hydrogen Bond Acceptor Count (hbondacc)

7

Chemical Identifiers

Formula: C11H13N5O3
IUPAC Name: (1S,2R,5R)-5-(6-aminopurin-9-yl)-3-(hydroxymethyl)cyclopent-3-ene-1,2-diol
Canonical SMILES: C1=C([C@H]([C@H]([C@@H]1N2C=NC3=C(N=CN=C32)N)O)O)CO
InChI: InChI=1S/C11H13N5O3/c12-10-7-11(14-3-13-10)16(4-15-7)6-1-5(2-17)8(18)9(6)19/h1,3-4,6,8-9,17-19H,2H2,(H2,12,13,14)/t6-,8-,9+/m1/s1
InChIKey: XUGWUUDOWNZAGW-VDAHYXPESA-N

Cross-matching ID

PubChem CID: 72968
CAS Number: 72877-50-0
TTD ID: D0R2QS

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Adenosylhomocysteinase (AHCY)	TTE2KUJ	SAHH_HUMAN	Inhibitor	[2]
Thyroid hormone receptor (THR)	TTQWUPT	NOUNIPROTAC	Antagonist	[1]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Design of thyroid hormone receptor antagonists from first principles. J Steroid Biochem Mol Biol. 2002 Dec;83(1-5):59-73.
2	Molecular approaches for the treatment of hemorrhagic fever virus infections. Antiviral Res. 1993 Sep;22(1):45-75.
3	Sobetirome: a case history of bench-to-clinic drug discovery and development. Heart Fail Rev. 2010 Mar;15(2):177-82.
4	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
5	Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase. Bioorg Med Chem. 2008 Apr 1;16(7):3809-15.
6	How many drug targets are there Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
7	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
8	Design, synthesis, and molecular modeling studies of 5'-deoxy-5'-ureidoadenosine: 5'-ureido group as multiple hydrogen bonding donor in the active ... Bioorg Med Chem Lett. 2007 Aug 15;17(16):4456-9.
9	Synthesis of 5'-functionalized nucleosides: S-Adenosylhomocysteine analogues with the carbon-5' and sulfur atoms replaced by a vinyl or halovinyl u... Bioorg Med Chem. 2008 May 15;16(10):5424-33.
10	Synthesis of 4'-modified noraristeromycins to clarify the effect of the 4'-hydroxyl groups for inhibitory activity against S-adenosyl-L-homocystein... Bioorg Med Chem Lett. 2008 Apr 15;18(8):2615-8.
11	Synthesis of 5'-substituted fluoro-neplanocin A analogues: importance of a hydrogen bonding donor at 5'-position for the inhibitory activity of S-a... Bioorg Med Chem Lett. 2004 Nov 15;14(22):5641-4.