CMP-Neu5Ac

HCID 448209
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Basic information

CAS
3063-71-6
Standard SMILES
CC(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)O[C@](OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(N)nc3=O)[C@H](O)[C@@H]2O)(C(=O)O)C[C@@H]1O
InChIKey
TXCIAUNLDRJGJZ-BILDWYJOSA-N
Molecular formula
C20H31N4O16P
Average molar mass
614.5 g/mol
Monoisotopic mass
614.14726791

Names & identifiers

Preferred name
CMP-Neu5Ac
IUPAC
(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
English name
CYTIDINE 5'-MONOPHOSPHO-N-
Molecular formula
C20H31N4O16P
Molecular weight
614.45

Names & synonyms

3063-71-6cytidine monophosphate N-acetylneuraminic acidCmp-nanaCMP-N-acetylneuraminic acidAcetylneuraminic acid, CMPCMP acetylneuraminic acidCMP-Neu5Ac(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 acidD-glycero-beta-D-galacto-2-Nonulopyranosonic acid, 5-(acetylamino)-3,5-dideoxy-, 2-(hydrogen 5'-cytidylate)DTXSID10904348CMP Sialic acidCMP N Acetylneuraminic Acid
Show more names
cmp-nanCMP-SiaCMP-NeuAcCYTIDINE 5'-MONOPHOSPHO-N-CMP-N-acetyl-β-neuraminicaciCMP-Sialic Acid, Disodium Salt
(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 acidRefChem:388909Cytidine monophosphate N acetylneuraminic acidDTXCID801333505CMP-Sialic acidCMP-N-acetylneuraminateCMP-NeuNAccytidine-5'-monophospho-N-acetylneuraminic acid

Database identifiers

CAS
3063-71-6
PubChem CID
448209
ChEMBL
CHEMBL1234647
ChEBI
CHEBI:16556
UNII
T8I6M8AXA0
Nikkaji
J838.846F

Properties

Computed structural properties

XLogP
-6.7
Topological polar surface area
321 Ų
Hydrogen bond donors
10
Hydrogen bond acceptors
16
Rotatable bonds
11
Heavy atoms
41

Experimental & physicochemical properties

Physical DescriptionSolid
Collision Cross Section215.5 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]；220.7 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Density
2.02 · 2.02±0.1 g/cm3(Predicted)
storage temp.
-20 °C · -20°C
pka
1.3 · 1.30±0.50(Predicted)
form
solid
color
white
Water Solubility
20 mg/mL · water: 20mg/mL

Safety & regulation

Safety data

F
10-21
wgk
3
risk_code
36/37/38
safety_code
26
Storage Class
13 - Non Combustible Solids

Chemistry & industry

Pharmacology

Tissue LocationsPlacenta
Cellular LocationsCytoplasm；Golgi apparatus；Nucleus
Metabolite PathwaysAmino Sugar Metabolism；G(M2)-Gangliosidosis: Variant B, Tay-sachs disease；Salla Disease/Infantile Sialic Acid Storage Disease；Sialuria or French Type Sialuria；Tay-Sachs Disease
Applications · 2 items

UsesCytidine-5′-monophospho-N-acetylneuraminic acid sodium salt has been used: as a standard in high-performance anion-exchange chromatography with pulsed amperometric detection (HPAEC-PAD) for nucleotide sugar analysis in Joubert syndrome type 10 (JBTS10) patient cells and control skin fibroblasts, As a substrate for the enzymatic sialylation of G2 glycoforms, resialylation assay, in in-vitro sialyltransferase assay

General DescriptionCytosine 5′-monophosphate N-acetylneuraminic acid (CMP-Neu5Ac) is a sugar-nucleotide produced by CMP-Neu5Ac synthetase from CTP and Neu5Ac.

Upstream & downstream products

Suppliers82 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
武汉敬康恩生物医药科技有限公司13720134139 086-15871494362 13720134139 · [email protected]
毕佳索（上海毕得医药科技股份有限公司）400-6005915 · [email protected]
Additional notes · 1 item

DefinitionChEBI: CMP-N-acetyl-beta-neuraminic acid is a nucleotide sugar used as a donor by glycosyltransferases for the synthesis of sugar chains It has a role as a mouse metabolite. It is functionally related to a N-acetyl-beta-neuraminic acid. It is a conjugate acid of a CMP-N-acetyl-beta-neuraminate(2-).

Related reactions

5 records
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Compound notes

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