MiMeDB: Showing metabocard for N-acetyl-alpha-D-glucosamine 1-phosphate (MMDBc0033114)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:35:22 UTC

Update Date

2022-08-31 22:26:19 UTC

MiMeDB ID

MMDBc0033114

Metabolite Identification

Common Name

N-acetyl-alpha-D-glucosamine 1-phosphate

Description

N-Acetyl-glucosamine 1-phosphate is an intermediate in the aminosugars metabolism. This compound is a substrate for the enzymes phosphoglucomutase 3 [EC:5.4.2.2 5.4.2.3] and UDP-N-acteylglucosamine pyrophosphorylase 1 [EC:2.7.7.23]. It is involved in UDP-N-acetyl-D-glucosamine biosynthesis and UDP-N-acetylgalactosamine biosynthesis. [KEGG]

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307301920012D          

 19 19  0  0  1  0            999 V2000
    0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  1  6  0  0  0
  1  2  1  0  0  0  0
  3  1  1  0  0  0  0
  3  7  1  6  0  0  0
  3  4  1  0  0  0  0
  4  8  1  1  0  0  0
  4  5  1  0  0  0  0
  5 10  1  6  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  6 11  1  1  0  0  0
  7  9  1  0  0  0  0
  9 13  2  0  0  0  0
  9 14  1  0  0  0  0
 11 12  1  0  0  0  0
 15 18  1  0  0  0  0
 18 16  2  0  0  0  0
 18 17  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033114

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8-/m1/s1

> <INCHI_KEY>
FZLJPEPAYPUMMR-FMDGEEDCSA-N

> <FORMULA>
C8H16NO9P

> <MOLECULAR_WEIGHT>
301.1877

> <EXACT_MASS>
301.056267627

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.3125788547967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

> <JCHEM_LOGP>
-3.3441404429999997

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.238176777203131

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1769426926362891

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5739791759132924

> <JCHEM_POLAR_SURFACE_AREA>
165.78

> <JCHEM_REFRACTIVITY>
57.8976

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
D-glucosamine 1-phosphate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.667  -1.540   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001   0.770   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0       2.667   3.080   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
CONECT    1   15    2    3                                                  
CONECT    2    1    6                                                       
CONECT    3    1    7    4                                                  
CONECT    4    3    8    5                                                  
CONECT    5    4   10    6                                                  
CONECT    6    5    2   11                                                  
CONECT    7    3    9                                                       
CONECT    8    4                                                            
CONECT    9    7   13   14                                                  
CONECT   10    5                                                            
CONECT   11    6   12                                                       
CONECT   12   11                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15    1   18                                                       
CONECT   16   18                                                            
CONECT   17   18                                                            
CONECT   18   15   16   17   19                                             
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

Synonyms

Value	Source
1-(N-Acetyl-alpha-D-glucosamine) phosphate	ChEBI
2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-ALPHA-D-glucopyranose	ChEBI
2-Acetamido-2-deoxy-1-O-phosphono-alpha-D-glucopyranose	ChEBI
2-N-Acetylglucosamine 1-phosphate	ChEBI
alpha-GlcNAc-(1->o)PO3H2	ChEBI
alpha-GlcNAc-1-p	ChEBI
GlcNAc1alpha-phosphate	ChEBI
N-Acetyl-alpha-D-glucosamine 1-(dihydrogen phosphate)	ChEBI
N-Acetylglucosamine-1-phosphate	ChEBI
1-(N-Acetyl-a-D-glucosamine) phosphate	Generator
1-(N-Acetyl-a-D-glucosamine) phosphoric acid	Generator
1-(N-Acetyl-alpha-D-glucosamine) phosphoric acid	Generator
1-(N-Acetyl-α-D-glucosamine) phosphate	Generator
1-(N-Acetyl-α-D-glucosamine) phosphoric acid	Generator
2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-a-D-glucopyranose	Generator
2-(ACETYLAMINO)-2-deoxy-1-O-phosphono-α-D-glucopyranose	Generator
2-Acetamido-2-deoxy-1-O-phosphono-a-D-glucopyranose	Generator
2-Acetamido-2-deoxy-1-O-phosphono-α-D-glucopyranose	Generator
2-N-Acetylglucosamine 1-phosphoric acid	Generator
a-GlcNAc-(1->o)PO3H2	Generator
Α-glcnac-(1->o)PO3H2	Generator
a-GlcNAc-1-p	Generator
Α-glcnac-1-p	Generator
GlcNAc1a-phosphate	Generator
GlcNAc1a-phosphoric acid	Generator
GlcNAc1alpha-phosphoric acid	Generator
GlcNAc1α-phosphate	Generator
GlcNAc1α-phosphoric acid	Generator
N-Acetyl-a-D-glucosamine 1-(dihydrogen phosphate)	Generator
N-Acetyl-a-D-glucosamine 1-(dihydrogen phosphoric acid)	Generator
N-Acetyl-alpha-D-glucosamine 1-(dihydrogen phosphoric acid)	Generator
N-Acetyl-α-D-glucosamine 1-(dihydrogen phosphate)	Generator
N-Acetyl-α-D-glucosamine 1-(dihydrogen phosphoric acid)	Generator
N-Acetylglucosamine-1-phosphoric acid	Generator
N-Acetyl-α-D-glucosamine 1-phosphoric acid	Generator
N-Acetyl-a-D-glucosamine 1-phosphate	Generator
N-Acetyl-a-D-glucosamine 1-phosphoric acid	Generator
N-Acetyl-alpha-D-glucosamine 1-phosphoric acid	Generator
N-Acetyl-α-D-glucosamine 1-phosphate	Generator
GlcNAc-1-phosphate	MeSH

Chemical Formula

C₈H₁₆NO₉P

Average Molecular Weight

301.1877

Monoisotopic Molecular Weight

301.056267627

IUPAC Name

{[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid

Traditional Name

D-glucosamine 1-phosphate

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OP(O)(O)=O

InChI Identifier

InChI=1S/C8H16NO9P/c1-3(11)9-5-7(13)6(12)4(2-10)17-8(5)18-19(14,15)16/h4-8,10,12-13H,2H2,1H3,(H,9,11)(H2,14,15,16)/t4-,5-,6-,7-,8-/m1/s1

InChI Key

FZLJPEPAYPUMMR-FMDGEEDCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acyl-alpha-hexosamines

Alternative Parents

Substituents

N-acyl-alpha-hexosamine
Hexose monosaccharide
Monosaccharide phosphate
Monoalkyl phosphate
Monosaccharide
Organic phosphoric acid derivative
Oxane
Phosphoric acid ester
Alkyl phosphate
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Primary alcohol
Carbonyl group
Organonitrogen compound
Organic oxide
Alcohol
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

2-acetamido-2-deoxy-D-glucopyranose 1-phosphate (CHEBI:16446 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
logP	-3.3	ChemAxon
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	165.78 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	57.9 m³·mol⁻¹	ChemAxon
Polarizability	25.31 Å³	ChemAxon
Number of Rings	1	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	splash10-007k-9230000000-37cdd3ef185356d03c19	2016-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1094000000-f1e04aaf05d431b8b0ab	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7k-6290000000-6ff96a8c8bf54d5e8bfa	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f6t-9620000000-3e2ee2ffc3801abdb7da	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002s-9211000000-7f3631860a58ca188060	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9110000000-9614f2b717f8fb17cc08	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-1a4f6aa02a49053d5b95	2016-09-12	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

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Fungi	Ascomycota	4	Human Feces	Unknown;
	Cyanobacteria	31	Human
	Firmicutes	137	Human Feces; Human ; Catfish ; Cattle
	Tenericutes	1
	Proteobacteria	362	Human ; Pig ; Cattle ; Rat ; Turkey ; Lion ; Chicken ; Human Feces
	Aquificae	2
	Actinobacteria	47	Human ; Human Feces; Cattle
	Deinococcus-Thermus	4
	Thermotogae	8
	Fusobacteria	1	Human
	Acidobacteria	2
Archaea	Euryarchaeota	6
		1
	Nitrospirae	1
NULL	Proteobacteria	1
Archaea	Crenarchaeota	1
Fungi	Microsporidia	1
Bamfordvirae	Nucleocytoviricota	1

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

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

FDB031023

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C04501

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440364

PDB ID

Not Available

ChEBI ID

16446

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 N-acetyl-alpha-D-glucosamine 1-phosphate (MMDBc0033114)

MOL for #<Metabolite:0x0000564abf83b9f8>

3D MOL for #<Metabolite:0x0000564abf83b9f8>

3D SDF for #<Metabolite:0x0000564abf83b9f8>

3D-SDF for #<Metabolite:0x0000564abf83b9f8>

PDB for #<Metabolite:0x0000564abf83b9f8>

3D PDB for #<Metabolite:0x0000564abf83b9f8>

SMILES for #<Metabolite:0x0000564abf83b9f8>

INCHI for #<Metabolite:0x0000564abf83b9f8>

Structure for #<Metabolite:0x0000564abf83b9f8>

3D Structure for #<Metabolite:0x0000564abf83b9f8>