MiMeDB: Showing metabocard for 5-methyl-CMP (MMDBc0054282)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:04:26 UTC

Update Date

2024-10-11 01:13:39 UTC

Metabolite ID

MMDBc0054282

Metabolite Identification

Common Name

5-methyl-CMP

Description

5-methylcytidine 5'-monophosphate, also known as 5-methyl-CMP or 5-methylcytidylic 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. A pyrimidine ribonucleoside 5'-monophosphate having 5-methylcytosine as the nucleobase. 5-methylcytidine 5'-monophosphate is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05031422362D          

 26 27  0  0  1  0            999 V2000
   -4.3455   -0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401    0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251   -0.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1895   -0.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8841   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6744   -1.6491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690   -1.0679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    0.3532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636   -0.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122    2.0180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825    0.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726    2.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122    2.6151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596    2.8935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187    2.6201    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    1.1497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  1  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  2  1  0  0  0  0
  9 13  1  1  0  0  0
 13 10  1  0  0  0  0
  6 14  1  6  0  0  0
  7 15  1  6  0  0  0
 16 10  1  0  0  0  0
 20  3  1  0  0  0  0
 21  5  1  0  0  0  0
 21  9  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  2  0  0  0  0
 22 20  1  0  0  0  0
  5 23  1  6  0  0  0
  6 24  1  1  0  0  0
  7 25  1  1  0  0  0
  9 26  1  6  0  0  0
M  END


  Mrv0541 05031422362D          

 26 27  0  0  1  0            999 V2000
   -4.3455   -0.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401    0.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5251   -0.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1895   -0.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8841   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6744   -1.6491    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3690   -1.0679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    0.3532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636   -0.4867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3122    2.0180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825    0.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2726    2.5477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    1.5082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8122    2.6151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596    2.8935    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1187    2.6201    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496    1.1497    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  1  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  1  0  0  0  0
  9  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12 10  2  0  0  0  0
 13  2  1  0  0  0  0
  9 13  1  1  0  0  0
 13 10  1  0  0  0  0
  6 14  1  6  0  0  0
  7 15  1  6  0  0  0
 16 10  1  0  0  0  0
 20  3  1  0  0  0  0
 21  5  1  0  0  0  0
 21  9  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
 22 19  2  0  0  0  0
 22 20  1  0  0  0  0
  5 23  1  6  0  0  0
  6 24  1  1  0  0  0
  7 25  1  1  0  0  0
  9 26  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054282

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=C(C)C(=N)N=C2O)[C@]([H])(O)[C@]1([H])O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N3O8P/c1-4-2-13(10(16)12-8(4)11)9-7(15)6(14)5(21-9)3-20-22(17,18)19/h2,5-7,9,14-15H,3H2,1H3,(H2,11,12,16)(H2,17,18,19)/t5-,6-,7-,9-/m1/s1

> <INCHI_KEY>
NJQONZSFUKNYOY-JXOAFFINSA-N

> <FORMULA>
C10H16N3O8P

> <MOLECULAR_WEIGHT>
337.2231

> <EXACT_MASS>
337.067501015

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
29.056790208385127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-5-methyl-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}phosphonic acid

> <ALOGPS_LOGP>
-1.87

> <JCHEM_LOGP>
-2.707572191704098

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.250888249692883

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.201194084908125

> <JCHEM_PKA_STRONGEST_BASIC>
2.485353168852959

> <JCHEM_POLAR_SURFACE_AREA>
176.13

> <JCHEM_REFRACTIVITY>
81.1873

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-5-methylpyrimidin-1-yl)oxolan-2-yl]methoxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM   23  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.000   0.000   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    4   13                                                       
CONECT    3    5   20                                                       
CONECT    4    1    2    8                                                  
CONECT    5    3    6   21   23                                             
CONECT    6    5    7   14   24                                             
CONECT    7    6    9   15   25                                             
CONECT    8    4   11   12                                                  
CONECT    9    7   13   21   26                                             
CONECT   10   12   13   16                                                  
CONECT   11    8                                                            
CONECT   12    8   10                                                       
CONECT   13    2    9   10                                                  
CONECT   14    6                                                            
CONECT   15    7                                                            
CONECT   16   10                                                            
CONECT   17   22                                                            
CONECT   18   22                                                            
CONECT   19   22                                                            
CONECT   20    3   22                                                       
CONECT   21    5    9                                                       
CONECT   22   17   18   19   20                                             
CONECT   23    5                                                            
CONECT   24    6                                                            
CONECT   25    7                                                            
CONECT   26    9                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

Synonyms

Value	Source
5-Methyl-CMP	ChEBI
5-Methylcytidine 5'-phosphate	ChEBI
5-Methylcytidylic acid	ChEBI
5-Methylcytidine 5'-phosphoric acid	Generator
5-Methylcytidylate	Generator
5-Methylcytidine 5'-monophosphoric acid	Generator

Molecular Formula

C₁₀H₁₆N₃O₈P

Average Mass

337.2231

Monoisotopic Mass

337.067501015

IUPAC Name

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

Traditional Name

[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-5-methylpyrimidin-1-yl)oxolan-2-yl]methoxyphosphonic acid

CAS Registry Number

Not Available

SMILES

[H][C@]1(COP(O)(O)=O)O[C@@]([H])(N2C=C(C)C(=N)N=C2O)[C@]([H])(O)[C@]1([H])O

InChI Identifier

InChI=1S/C10H16N3O8P/c1-4-2-13(10(16)12-8(4)11)9-7(15)6(14)5(21-9)3-20-22(17,18)19/h2,5-7,9,14-15H,3H2,1H3,(H2,11,12,16)(H2,17,18,19)/t5-,6-,7-,9-/m1/s1

InChI Key

NJQONZSFUKNYOY-JXOAFFINSA-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:74725 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	4.15 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-2.7	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	1.2	ChemAxon
pKa (Strongest Basic)	2.49	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	176.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.19 m³·mol⁻¹	ChemAxon
Polarizability	29.06 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9601000000-4c8b0c0bdefc67b22a1f	2017-08-28	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0901000000-469f01d20625411713f0	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-3900000000-c6a256edb747c9ff5edb	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004i-4900000000-eb089492ef1d4438f89c	2017-07-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-009l-9858000000-502568f7df5509893660	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-b84c8d44352ba9d69df1	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-d6440a8478a582c4f542	2017-07-26	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human feces
Bacteria	Proteobacteria	1

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

DB01995

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

192785

PDB ID

Not Available

ChEBI ID

74725

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for 5-methyl-CMP (MMDBc0054282)

MOL for #<Metabolite:0x00007fdb43de0d98>

3D MOL for #<Metabolite:0x00007fdb43de0d98>

3D SDF for #<Metabolite:0x00007fdb43de0d98>

3D-SDF for #<Metabolite:0x00007fdb43de0d98>

PDB for #<Metabolite:0x00007fdb43de0d98>

3D PDB for #<Metabolite:0x00007fdb43de0d98>

SMILES for #<Metabolite:0x00007fdb43de0d98>

INCHI for #<Metabolite:0x00007fdb43de0d98>

Structure for #<Metabolite:0x00007fdb43de0d98>

3D Structure for #<Metabolite:0x00007fdb43de0d98>