MiMeDB: Showing metabocard for N-acetyl-alpha-D-hexosamine 1-phosphate (MMDBc0054574)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:18:46 UTC

Update Date

2022-08-12 20:09:01 UTC

Metabolite ID

MMDBc0054574

Metabolite Identification

Common Name

N-acetyl-alpha-D-hexosamine 1-phosphate

Description

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006051512232D          
 
 19 19  0  0  1  0            999 V2000
   15.2140  -11.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2140  -10.9173    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4950  -12.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4950  -10.5049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9256  -10.5049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7797  -11.7423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4950  -12.9762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7797  -10.9173    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   15.9256   -9.6798    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0758  -12.1549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0758  -10.5049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9256   -8.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7506   -9.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1043   -9.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4476  -11.0385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9456  -12.1588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6718  -11.7395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3980  -12.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6718  -10.9011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  6  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  1  0  0  0
  9 12  2  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 11 15  1  0  0  0  0
  6  8  1  0  0  0  0
  1 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054574

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)NC1C(O)C(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-YVKWHVBHSA-N

> <FORMULA>
C8H16NO9P

> <MOLECULAR_WEIGHT>
301.188

> <EXACT_MASS>
301.056268097

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
25.370403076193597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-3.3441404429999997

> <ALOGPS_LOGS>
-1.21

> <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>
-1.5739791759132933

> <JCHEM_POLAR_SURFACE_AREA>
165.78

> <JCHEM_REFRACTIVITY>
57.8976

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.84e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-JUN-15         0                                  
HETATM    1  C   UNK     0      28.400 -21.919   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.400 -20.379   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      27.057 -22.689   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.057 -19.609   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      29.728 -19.609   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      25.722 -21.919   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      27.057 -24.222   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      25.722 -20.379   0.000  0.00  0.00           C+0
HETATM    9  P   UNK     0      29.728 -18.069   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0      24.408 -22.689   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      24.408 -19.609   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      29.728 -16.536   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      31.268 -18.069   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      28.195 -18.069   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      23.236 -20.605   0.000  0.00  0.00           O+0
HETATM   16  N   UNK     0      29.765 -22.696   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      31.121 -21.914   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.476 -22.696   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      31.121 -20.349   0.000  0.00  0.00           O+0
CONECT    1    2    3   16                                                  
CONECT    2    1    4    5                                                  
CONECT    3    1    6    7                                                  
CONECT    4    2    8                                                       
CONECT    5    2    9                                                       
CONECT    6    3   10    8                                                  
CONECT    7    3                                                            
CONECT    8    4   11    6                                                  
CONECT    9    5   12   13   14                                             
CONECT   10    6                                                            
CONECT   11    8   15                                                       
CONECT   12    9                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   11                                                            
CONECT   16    1   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

Synonyms

Value	Source
N-Acetyl-a-D-hexosamine 1-phosphate	Generator
N-Acetyl-a-D-hexosamine 1-phosphoric acid	Generator
N-Acetyl-alpha-D-hexosamine 1-phosphoric acid	Generator
N-Acetyl-α-D-hexosamine 1-phosphate	Generator
N-Acetyl-α-D-hexosamine 1-phosphoric acid	Generator

Molecular Formula

C₈H₁₆NO₉P

Average Mass

301.188

Monoisotopic Mass

301.056268097

IUPAC Name

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

Traditional Name

[(2R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC1C(O)C(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-YVKWHVBHSA-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

phospho sugar (CHEBI:81474 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	18.4 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.3	ChemAxon
logS	-1.2	ALOGPS
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	25.37 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 (TMS_5_4) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-2096000000-e53b25491484b97a9340	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0f7n-8291000000-0484625ad8ff2894f4ef	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9310000000-5ab12a446ee7c0ab5907	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002s-9201000000-056a55d3c4355491d46a	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-7f15395993bd262d2b95	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-0fc2f90e4614dde0255f	2019-02-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	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	Actinobacteria	1	Human ; Human feces

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

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

C18055

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46174044

PDB ID

Not Available

ChEBI ID

81474

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-hexosamine 1-phosphate (MMDBc0054574)

MOL for #<Metabolite:0x00007feca865dff0>

3D MOL for #<Metabolite:0x00007feca865dff0>

3D SDF for #<Metabolite:0x00007feca865dff0>

3D-SDF for #<Metabolite:0x00007feca865dff0>

PDB for #<Metabolite:0x00007feca865dff0>

3D PDB for #<Metabolite:0x00007feca865dff0>

SMILES for #<Metabolite:0x00007feca865dff0>

INCHI for #<Metabolite:0x00007feca865dff0>

Structure for #<Metabolite:0x00007feca865dff0>

3D Structure for #<Metabolite:0x00007feca865dff0>