MiMeDB: Showing metabocard for MurNAc-6-P (MMDBc0032155)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 02:04:41 UTC

Update Date

2022-08-31 18:30:57 UTC

Metabolite ID

MMDBc0032155

Metabolite Identification

Common Name

MurNAc-6-P

Description

N-Acetylmuramic acid 6-phosphate (MurNAc-6-P) is a member of the chemical class known as Sugar Acids and Derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group. The enzyme MurQ is an N-acetylmuramic acid 6-phosphate (MurNAc 6-phosphate) hydrolase (or etherase) that hydrolyzes the lactyl side chain from MurNAc 6-phosphate and generates GlcNAc 6-phosphate. (PMID 18837509 ). It is a key component of peptidoglycan synthesis. The peptidoglycan synthesis pathway starts at the cytoplasm, where in six steps the peptidoglycan precursor a UDP-N-acetylmuramoyl-pentapeptide is synthesized. This precursor is then attached to the memberane acceptor all-trans-undecaprenyl phosphate, generating a N-acetylmuramoyl-pentapeptide-diphosphoundecaprenol, also known as lipid I. Another transferase then adds UDP-N-acetyl-alpha-D-glucosamine, yielding the complete monomeric unit a lipid , also known as lipid . This final lipid intermediate is transferred through the membrane. The peptidoglycan monomers are then polymerized on the outside surface by glycosyltransferases, which form the linear glycan chains, and transpeptidases, which catalyze the formation of peptide crosslinks.

Structure

MOL SDF PDB SMILES InChI


  Mrv1533005041515592D          

 24 24  0  0  0  0            999 V2000
    1.0717    1.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    1.8009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3572    1.3884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.5634    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3572    0.1509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0717    0.5634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -0.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0717   -1.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717   -1.9115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -2.3240    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006   -2.7365    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1986   -1.6095    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.3736   -3.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.6740    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7861   -1.0865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.1509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7861    0.5634    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861    1.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    1.8009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006    1.8009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    2.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    3.0384    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.0717    3.0384    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 13  2  0  0  0  0
  7 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  CHG  3  11  -1  12  -1  23  -1
M  END
> <DATABASE_ID>
MMDBc0032155

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@@H](O[C@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@@H](O)[C@@H]1NC(C)=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H20NO11P/c1-4(10(15)16)22-9-7(12-5(2)13)11(17)23-6(8(9)14)3-21-24(18,19)20/h4,6-9,11,14,17H,3H2,1-2H3,(H,12,13)(H,15,16)(H2,18,19,20)/p-3/t4-,6-,7-,8-,9-,11-/m1/s1

> <INCHI_KEY>
NMEMTQKUEVNSPV-YVNCZSHWSA-K

> <FORMULA>
C11H17NO11P

> <MOLECULAR_WEIGHT>
370.228

> <EXACT_MASS>
370.055568109

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
31.508150222961223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
-3

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate

> <ALOGPS_LOGP>
-1.44

> <JCHEM_LOGP>
-2.6542663886666666

> <ALOGPS_LOGS>
-1.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.5412678613086905

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2211466675153453

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5737313540209539

> <JCHEM_POLAR_SURFACE_AREA>
200.57

> <JCHEM_REFRACTIVITY>
81.82100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.28e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-15         0                                  
HETATM    1  C   UNK     0       2.001   2.592   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.667   3.362   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.667   2.592   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.667   1.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.667   0.282   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.001   1.052   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.667  -1.258   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.001  -2.028   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.001  -3.568   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0       3.334  -4.338   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0       4.668  -5.108   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0       4.104  -3.004   0.000  0.00  0.00           O-1
HETATM   13  O   UNK     0       2.564  -5.672   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.667  -2.028   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.001  -1.258   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.334  -2.028   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.001   0.282   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0      -3.334   1.052   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      -3.334   2.592   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.001   3.362   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.668   3.362   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.667   4.902   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.667   5.672   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0       2.001   5.672   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   22                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
CONECT   14    7   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    4   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22    2   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

Synonyms

Value	Source
2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-beta-D-glucopyranose	ChEBI
N-Acetyl-beta-D-muramate 6-phosphate	ChEBI
2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-b-D-glucopyranose	Generator
2-Acetamido-3-O-[(1R)-1-carboxylatoethyl]-2-deoxy-6-O-phosphonato-β-D-glucopyranose	Generator
N-Acetyl-b-D-muramate 6-phosphate	Generator
N-Acetyl-b-D-muramic acid 6-phosphoric acid	Generator
N-Acetyl-beta-D-muramic acid 6-phosphoric acid	Generator
N-Acetyl-β-D-muramate 6-phosphate	Generator
N-Acetyl-β-D-muramic acid 6-phosphoric acid	Generator
N-Acetyl-b-muramate 6-phosphate	Generator
N-Acetyl-b-muramic acid 6-phosphoric acid	Generator
N-Acetyl-beta-muramic acid 6-phosphoric acid	Generator
N-Acetyl-β-muramate 6-phosphate	Generator
N-Acetyl-β-muramic acid 6-phosphoric acid	Generator

Molecular Formula

C₁₁H₁₇NO₁₁P

Average Mass

370.228

Monoisotopic Mass

370.055568109

IUPAC Name

(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate

Traditional Name

(2R)-2-{[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-[(phosphonatooxy)methyl]oxan-4-yl]oxy}propanoate

CAS Registry Number

Not Available

SMILES

C[C@@H](O[C@H]1[C@H](O)[C@@H](COP([O-])([O-])=O)O[C@@H](O)[C@@H]1NC(C)=O)C([O-])=O

InChI Identifier

InChI=1S/C11H20NO11P/c1-4(10(15)16)22-9-7(12-5(2)13)11(17)23-6(8(9)14)3-21-24(18,19)20/h4,6-9,11,14,17H,3H2,1-2H3,(H,12,13)(H,15,16)(H2,18,19,20)/p-3/t4-,6-,7-,8-,9-,11-/m1/s1

InChI Key

NMEMTQKUEVNSPV-YVNCZSHWSA-K

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminosugars. These are organic compounds containing a sugar linked to a chain through N-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Acylaminosugars

Alternative Parents

Substituents

Acylaminosugar
Muramic_acid
Hexose phosphate
N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide phosphate
Sugar acid
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Secondary alcohol
Carboxamide group
Secondary carboxylic acid amide
Hemiacetal
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organonitrogen compound
Alcohol
Organopnictogen compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic nitrogen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate acid derivative anion (CHEBI:58721 )
monocarboxylic acid anion (CHEBI:58721 )
organophosphate oxoanion (CHEBI:58721 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	42.8 g/L	ALOGPS
logP	-1.4	ALOGPS
logP	-2.7	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	1.22	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	200.57 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	81.82 m³·mol⁻¹	ChemAxon
Polarizability	31.51 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0009000000-26840ebd21fec14e617e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1019000000-b294b39df58c9a255db0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pbc-9350000000-56946c4648b358d38b01	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-1309000000-bc198272687956621edb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ldi-9706000000-569d6ad0644babab8157	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a1479163c82b87678df2	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-18	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	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown

Exposure Sources

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

Not Available

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

45266739

PDB ID

Not Available

ChEBI ID

58721

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]

Showing metabocard for MurNAc-6-P (MMDBc0032155)

MOL for #<Metabolite:0x00007fdb0328d878>

3D MOL for #<Metabolite:0x00007fdb0328d878>

3D SDF for #<Metabolite:0x00007fdb0328d878>

3D-SDF for #<Metabolite:0x00007fdb0328d878>

PDB for #<Metabolite:0x00007fdb0328d878>

3D PDB for #<Metabolite:0x00007fdb0328d878>

SMILES for #<Metabolite:0x00007fdb0328d878>

INCHI for #<Metabolite:0x00007fdb0328d878>

Structure for #<Metabolite:0x00007fdb0328d878>

3D Structure for #<Metabolite:0x00007fdb0328d878>