Details of the Drug

General Information of Drug (ID: DMH48YE)

Drug Name

CMP-sialic acid

Synonyms

CMP-Sialic acid; CMP-N-acetylneuraminate; cytidine monophosphate N-acetylneuraminic acid; CMP-NeuNAc; CYTIDINE-5'-MONOPHOSPHATE-5-N-ACETYLNEURAMINIC ACID; Cmp-D-N-acetylneuraminic acid; CHEBI:16556; Cmp-nana; CMP acetylneuraminic acid; 3063-71-6; CMP-N-acetyl-beta-neuraminate; NCC; (2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

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 is unavailable

2D MOL

#Ro5 Violations (Lipinski): 5

Molecular Weight (mw)

614.5

Logarithm of the Partition Coefficient (xlogp)

-6.7

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

Chemical Identifiers

Formula: C20H31N4O16P
IUPAC Name: (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Canonical SMILES: CC(=O)N[C@@H]1[C@H](C[C@](O[C@H]1[C@@H]([C@@H](CO)O)O)(C(=O)O)OP(=O)(O)OC[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=CC(=NC3=O)N)O)O)O
InChI: InChI=1S/C20H31N4O16P/c1-7(26)22-12-8(27)4-20(18(32)33,39-16(12)13(29)9(28)5-25)40-41(35,36)37-6-10-14(30)15(31)17(38-10)24-3-2-11(21)23-19(24)34/h2-3,8-10,12-17,25,27-31H,4-6H2,1H3,(H,22,26)(H,32,33)(H,35,36)(H2,21,23,34)/t8-,9+,10+,12+,13+,14+,15+,16+,17+,20+/m0/s1
InChIKey: TXCIAUNLDRJGJZ-BILDWYJOSA-N

Cross-matching ID

PubChem CID: 448209
ChEBI ID: CHEBI:16556
CAS Number: 3063-71-6
DrugBank ID: DB02485
TTD ID: D07THV
VARIDT ID: DR00114

Molecular Interaction Atlas of This Drug

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
CMP-sialic acid transporter (SLC35A1)	DTVZIRG	S35A1_HUMAN	Substrate	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
N-acylneuraminate cytidylyltransferase (CMAS)	OTFQJG3C	NEUA_HUMAN	Regulation of Drug Effects	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4663).
2	Disease mutations in CMP-sialic acid transporter SLC35A1 result in abnormal -dystroglycan O-mannosylation, independent from sialic acid. Hum Mol Genet. 2015 Apr 15;24(8):2241-6.
3	Protein Sialylation Regulates a Gene Expression Signature that Promotes Breast Cancer Cell Pathogenicity. ACS Chem Biol. 2016 Aug 19;11(8):2131-9. doi: 10.1021/acschembio.6b00433. Epub 2016 Jul 22.