ChemFOnt: Showing chemical card for {[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid (CFc000135628)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 22:08:41 UTC

Chemfont ID

CFc000135628

Molecule Identification

Common Name

{[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid

Definition

Cytidine monophosphate, also known as CMP or cytidylic acid, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Cytidine monophosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Cytidine monophosphate exists in all living species, ranging from bacteria to humans. In humans, cytidine monophosphate is involved in lactose synthesis. Outside of the human body, Cytidine monophosphate has been detected, but not quantified in, several different foods, such as vanilla, red beetroots, kiwis, garden tomato (var.), and german camomiles. This could make cytidine monophosphate a potential biomarker for the consumption of these foods. A pyrimidine ribonucleoside 5'-monophosphate having cytosine as the nucleobase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CMP	ChEBI
Cytidine-5'-monophosphate	ChEBI
Cytidylate	ChEBI
Cytidylic acid	ChEBI
pC	ChEBI
Cytidine-5'-monophosphoric acid	Generator
Cytidine monophosphoric acid	Generator
Cytidine 5'-monophosphate	HMDB
Cytidine 5'-monophosphoric acid	HMDB
5'-CMP	HMDB
5-Cytidylate	HMDB
5-Cytidylic acid	HMDB
Cytidine 5'-monophosphorate	HMDB
Cytidine 5'-phosphate	HMDB
Cytidine 5'-phosphorate	HMDB
Cytidine 5'-phosphoric acid	HMDB
Cytidine mono(dihydrogen phosphate)	HMDB
Acid, cytidylic	HMDB
monoPhosphate, cytidine	HMDB
5’-CMP	HMDB
Cytidine 5’-monophosphate	HMDB
Cytidine 5’-monophosphoric acid	HMDB
Cytidine 5’-phosphate	HMDB
Cytidine 5’-phosphoric acid	HMDB
Cytidine monophosphate	HMDB
Cytosine 5'-monophosphate	HMDB
Cytosine 5’-monophosphate	HMDB

Chemical Formula

C₉H₁₄N₃O₈P

Average Molecular Weight

323.1965

Monoisotopic Molecular Weight

323.051850951

IUPAC Name

{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

Traditional Name

cytidine monophosphate

CAS Registry Number

63-37-6

SMILES

NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

InChI Key

IERHLVCPSMICTF-XVFCMESISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine ribonucleotides

Direct Parent

Pyrimidine ribonucleoside monophosphates

Alternative Parents

Substituents

Pyrimidine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Pentose monosaccharide
Aminopyrimidine
Pyrimidone
Monoalkyl phosphate
Hydropyrimidine
Monosaccharide
Organic phosphoric acid derivative
Phosphoric acid ester
Pyrimidine
Alkyl phosphate
Imidolactam
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
1,2-diol
Oxacycle
Organoheterocyclic compound
Azacycle
Organopnictogen compound
Amine
Alcohol
Organic oxide
Organonitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic nitrogen compound
Primary amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrimidine ribonucleoside 5'-monophosphate (CHEBI:17361 )
cytidine 5'-phosphate (CHEBI:17361 )
Ribonucleotides (C00055 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	16.3 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.2	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	1.25	ChemAxon
pKa (Strongest Basic)	-0.15	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	175.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.42 m³·mol⁻¹	ChemAxon
Polarizability	26.9 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0000095

DrugBank ID

DB03403

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030736

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Cytidine monophosphate

METLIN ID

Not Available

PubChem Compound

6131

PDB ID

Not Available

ChEBI ID

17361

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for {[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid (CFc000135628)

MOL for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

3D MOL for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

3D SDF for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

3D-SDF for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

PDB for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

3D PDB for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

SMILES for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

INCHI for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

Structure for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)

3D Structure for CFc000135628 ({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid)