MiMeDB: Showing metabocard for 4-O-beta-D-mannopyranosyl-N-acetyl-D-glucosamine (MMDBc0054276)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:03:40 UTC

Update Date

2022-09-01 02:28:15 UTC

Metabolite ID

MMDBc0054276

Metabolite Identification

Common Name

4-O-beta-D-mannopyranosyl-N-acetyl-D-glucosamine

Description

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006071509292D          
 
 26 27  0  0  1  0            999 V2000
   11.6575   -8.6701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6575   -7.8407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3661   -9.0884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9607   -9.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3661   -7.4336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9489   -7.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0862   -8.6701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3661   -9.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2520   -9.4756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0862   -7.8407    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
   10.2364   -7.8407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8395   -9.1219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5357   -9.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2520  -10.3050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7948   -7.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8395   -9.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8233   -9.4756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5357  -10.7234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9644  -10.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5110  -10.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1718  -10.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8233  -10.3050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1146   -9.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320  -11.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1109  -10.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4059   -9.4756    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
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  1  0  0  0
  9  4  1  1  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  6  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  4  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  1  0  0  0
 16 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  1  0  0  0
 18 24  1  1  0  0  0
 22 25  1  6  0  0  0
 23 26  1  0  0  0  0
  7 10  1  0  0  0  0
 18 22  1  0  0  0  0
M  END

 
  Mrv1533006071509292D          
 
 26 27  0  0  1  0            999 V2000
   11.6575   -8.6701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.6575   -7.8407    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3661   -9.0884    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.9607   -9.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3661   -7.4336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9489   -7.4336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0862   -8.6701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.3661   -9.9102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2520   -9.4756    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0862   -7.8407    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
   10.2364   -7.8407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8395   -9.1219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5357   -9.0686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2520  -10.3050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.7948   -7.4299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8395   -9.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8233   -9.4756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5357  -10.7234    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.9644  -10.7158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5110  -10.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1718  -10.3507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8233  -10.3050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.1146   -9.0686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5320  -11.5451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1109  -10.7121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4059   -9.4756    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
  1  4  1  6  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  3  8  1  1  0  0  0
  9  4  1  1  0  0  0
  5 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7 12  1  6  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  4  0  0  0
 12 16  1  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  1  0  0  0
 16 20  1  0  0  0  0
 16 21  2  0  0  0  0
 17 22  1  0  0  0  0
 17 23  1  1  0  0  0
 18 24  1  1  0  0  0
 22 25  1  6  0  0  0
 23 26  1  0  0  0  0
  7 10  1  0  0  0  0
 18 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0054276

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8-,9-,10+,11+,12-,13?,14+/m1/s1

> <INCHI_KEY>
KFEUJDWYNGMDBV-KTNASFDVSA-N

> <FORMULA>
C14H25NO11

> <MOLECULAR_WEIGHT>
383.35

> <EXACT_MASS>
383.142760629

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.41089727258698

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

> <ALOGPS_LOGP>
-2.80

> <JCHEM_LOGP>
-4.991410057333334

> <ALOGPS_LOGS>
-0.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.231138627153623

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.501288100055472

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083565282729

> <JCHEM_POLAR_SURFACE_AREA>
198.39999999999998

> <JCHEM_REFRACTIVITY>
79.43799999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUN-15         0                                  
HETATM    1  C   UNK     0      21.761 -16.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.761 -14.636   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.083 -16.965   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      20.460 -16.921   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      23.083 -13.876   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      20.438 -13.876   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.428 -16.184   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      23.083 -18.499   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      19.137 -17.688   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.428 -14.636   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      19.108 -14.636   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      25.834 -17.027   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0      17.800 -16.928   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      19.137 -19.236   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      25.750 -13.869   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      25.834 -18.554   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.470 -17.688   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.800 -20.017   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      20.467 -20.003   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      27.087 -19.314   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      24.587 -19.321   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      16.470 -19.236   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.147 -16.928   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      17.793 -21.551   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      15.140 -19.996   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      13.824 -17.688   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12   10                                                  
CONECT    8    3                                                            
CONECT    9    4   13   14                                                  
CONECT   10    5   15    7                                                  
CONECT   11    6                                                            
CONECT   12    7   16                                                       
CONECT   13    9   17                                                       
CONECT   14    9   18   19                                                  
CONECT   15   10                                                            
CONECT   16   12   20   21                                                  
CONECT   17   13   22   23                                                  
CONECT   18   14   24   22                                                  
CONECT   19   14                                                            
CONECT   20   16                                                            
CONECT   21   16                                                            
CONECT   22   17   25   18                                                  
CONECT   23   17   26                                                       
CONECT   24   18                                                            
CONECT   25   22                                                            
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

Synonyms

Value	Source
(GlcNAc)1 (man)1	ChEBI
2-Acetamido-2-deoxy-4-O-beta-D-mannopyranosyl-D-glucopyranose	ChEBI
4-O-beta-D-Mannopyranosyl-N-acetyl-D-glucosamine	ChEBI
beta-D-Man-(1->4)-D-glcnac	ChEBI
beta-D-Mannosyl-(1->4)-N-acetyl-D-glucosamine	ChEBI
Manbeta1-4glcnac	ChEBI
2-Acetamido-2-deoxy-4-O-b-D-mannopyranosyl-D-glucopyranose	Generator
2-Acetamido-2-deoxy-4-O-β-D-mannopyranosyl-D-glucopyranose	Generator
4-O-b-D-Mannopyranosyl-N-acetyl-D-glucosamine	Generator
4-O-Β-D-mannopyranosyl-N-acetyl-D-glucosamine	Generator
b-D-Man-(1->4)-D-glcnac	Generator
Β-D-man-(1->4)-D-glcnac	Generator
b-D-Mannosyl-(1->4)-N-acetyl-D-glucosamine	Generator
Β-D-mannosyl-(1->4)-N-acetyl-D-glucosamine	Generator
b-D-Manp-(1->4)-D-glcpnac	Generator
Β-D-manp-(1->4)-D-glcpnac	Generator

Molecular Formula

C₁₄H₂₅NO₁₁

Average Mass

383.35

Monoisotopic Mass

383.142760629

IUPAC Name

N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

Traditional Name

N-[(3R,4R,5S,6R)-2,4-dihydroxy-6-(hydroxymethyl)-5-{[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

CAS Registry Number

Not Available

SMILES

CC(=O)N[C@H]1C(O)O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]2O)[C@@H]1O

InChI Identifier

InChI=1S/C14H25NO11/c1-4(18)15-7-9(20)12(6(3-17)24-13(7)23)26-14-11(22)10(21)8(19)5(2-16)25-14/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5-,6-,7-,8-,9-,10+,11+,12-,13?,14+/m1/s1

InChI Key

KFEUJDWYNGMDBV-KTNASFDVSA-N

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
N-acyl-alpha-hexosamine
Disaccharide
Glycosyl compound
O-glycosyl compound
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Acetal
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Alcohol
Primary alcohol
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

glucosamine oligosaccharide (CHEBI:76821 )
amino disaccharide (CHEBI:76821 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	259 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-5	ChemAxon
logS	-0.17	ALOGPS
pKa (Strongest Acidic)	11.5	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	198.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.44 m³·mol⁻¹	ChemAxon
Polarizability	36.41 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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_34) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00yi-0179000000-d117b299438bee3a1a40	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uk9-0592000000-db6f5abfab26c98d8af4	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0wbc-5960000000-915e1f050484eedb63d2	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2492000000-1208b9128bdb1fd8688e	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0h90-7984000000-2636a4af2a05389c39e5	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-7910000000-dce1bda7d8788ebd90af	2019-02-23	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	Bacteroidetes	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

Not Available

BioCyc ID

CPD-16181

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71297235

PDB ID

Not Available

ChEBI ID

76821

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 4-O-beta-D-mannopyranosyl-N-acetyl-D-glucosamine (MMDBc0054276)

MOL for #<Metabolite:0x00005634c0ffba68>

3D MOL for #<Metabolite:0x00005634c0ffba68>

3D SDF for #<Metabolite:0x00005634c0ffba68>

3D-SDF for #<Metabolite:0x00005634c0ffba68>

PDB for #<Metabolite:0x00005634c0ffba68>

3D PDB for #<Metabolite:0x00005634c0ffba68>

SMILES for #<Metabolite:0x00005634c0ffba68>

INCHI for #<Metabolite:0x00005634c0ffba68>

Structure for #<Metabolite:0x00005634c0ffba68>

3D Structure for #<Metabolite:0x00005634c0ffba68>