2'-Deoxycytidine-5'-Monophosphate

HCID 13945

Substructure search Find similar structures

Basic information

CAS: 1032-65-1
Standard SMILES: Nc1ccn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)O)O2)c(=O)n1
InChIKey: NCMVOABPESMRCP-SHYZEUOFSA-N
Molecular formula: C9H14N3O7P
Average molar mass: 307.2 g/mol
Monoisotopic mass: 307.05693642

Overview

2'-deoxycytosine 5'-monophosphate is a pyrimidine 2'-deoxyribonucleoside 5'-monophosphate having cytosine as the nucleobase. It has a role as a mouse metabolite and an Escherichia coli metabolite. It is a pyrimidine 2'-deoxyribonucleoside 5'-monophosphate and a 2'-deoxycytidine phosphate. It is a conjugate acid of a 2'-deoxycytosine 5'-monophosphate(2-). It is an enantiomer of a 2-deoxy-5-O-phosphono-beta-L-ribofuranosylcytosine.

Names & identifiers

Preferred name: 2'-Deoxycytidine-5'-Monophosphate
IUPAC: [(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
English name: 2'-Deoxycytidine-5'-monophosphoric acid
Molecular formula: C9H14N3O7P
Molecular weight: 307.2

Names & synonyms

1032-65-1dCMPdeoxycytidine monophosphatedeoxycytidylic acid2'-DEOXYCYTIDINE-5'-MONOPHOSPHATE2'-Deoxycytidine 5'-monophosphateDeoxycytidylate5'-Cytidylic acid, 2'-deoxy-W7A9174XQLDTXSID20908251[(2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate{[(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl]methoxy}phosphonic acid

Show more names

dCMP.H2dCMP(2-)Deoxy-CMPDESOXYCYTIDYLIC ACID2'-Deoxycytidylic aciddeoxycytidinemonophosphatedCMP, Deoxycytidylic acid

Acid, DeoxycytidylicMonophosphate, Deoxycytidine(((2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3-hydroxyoxolan-2-yl)methoxy)phosphonic acid((2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3-hydroxyoxolan-2-yl)methyl dihydrogen phosphateRefChem:7185DTXCID3013767082'-Deoxycytidine-5'-monophosphoric acid2'-deoxy-5'-cytidylic acid

Database identifiers

CAS: 1032-65-1、13085-50-2、25609-92-1
PubChem CID: 13945
DTXSID: DTXSID20908251
ChEMBL: CHEMBL374699
ChEBI: CHEBI:15918
UNII: W7A9174XQL
EC Number: 213-849-9、235-995-2
Nikkaji: J14.407J

Properties

Computed structural properties

XLogP: -3.4
Topological polar surface area: 155 Å²
Hydrogen bond donors: 4
Hydrogen bond acceptors: 7
Rotatable bonds: 4
Heavy atoms: 20
Formal charge: 0
Complexity: 502

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15

Physical DescriptionSolid

Collision Cross Section · 5 items

162.4 Å² [M-H]- [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

166.62 Å² [M+Na]+ [CCS Type: DT; Method: stepped-field]

164 Å² [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

161 Å² [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine]

164.3 Å² [M+Na]+

Physicochemical properties

Melting point: 169 · 169-172 °C (dec.)
Boiling point: 633.8 · 633.8±65.0 °C(Predicted)
Density: 2.01 · 2.01±0.1 g/cm3(Predicted)
refractive index: 37 ° · 37 ° (C=1, H2O)
storage temp.: -20 °C · -20°C
solubility: 2 O: · H2O: 10 mg/mL, clear, colorless
form: Crystalline Powder
pka: 1.86 · 1.86±0.10(Predicted)
color: White
biological source: synthetic
Water Solubility: Soluble in water.
BRN: 41062 · 41062
InChI: InChI=1S/C9H14N3O7P/c10-7-1-2-12(9(14)11-7)8-3-5(13)6(19-8)4-18-20(15,16)17/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17)/t5-,6+,8+/m0/s1
InChIKey: NCMVOABPESMRCP-SHYZEUOFSA-N
SMILES: P(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)C[C@@H]1O)(O)(O)=O
CAS DataBase Reference: 1032 · 1032-65-1(CAS DataBase Reference)
FDA UNII: 7 A9174XQL · W7A9174XQL
UNSPSC Code: 41106305 · 41106305
NACRES: 51 · NA.51
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H332-H312
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xn,Xi
Risk Statements: 20 · 20/21/22-36/37/38
Safety Statements: 22 · 22-24/25-37/39-36-26
WGK Germany: 3 · 3
F: 10 · 10-21
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P321, P330, P362+P364, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Safety data

F: 10-21
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29349990
risk_code: 20/21/22-36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn,Xi
safety_code: 22-24/25-37/39-36-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H332-H312
Precautionary statements: P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501

Chemistry & industry

Pharmacology

Cellular LocationsLysosome

Metabolite PathwaysBeta Ureidopropionase Deficiency

Applications · 3 items

UsesA phosphorylated metabolite of the deoxyribonucleoside 2’Deoxycytidine. A constituent of Deoxyribonucleic acid. Studies show that it increases influenza virus antigen-induced immune cell proliferatio n.

Uses2'-Deoxycytidine-5'-monophosphate is used as a substrate of uridine monophosphate (UMP)/cytidine monophosphate (CMP) kinase (EC 2.7.4.4) to form dCDP which upon phosphorylation to dCTP supports DNA and RNA biosynthesis.

General Description2′-Deoxycytidine 5′-monophosphate is a deoxynucleotide building block via which DNA is made. It consists of a 2′-deoxy-β-D-ribofuranose, linked through an N-β-D-glycosidic linkage to a heterocycle nitrogen cytosine. It is phosphorylated at carbon C-5′.