MiMeDB: Showing metabocard for (S)-malyl N-acetyl-alpha-D-glucosaminide (MMDBc0055070)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:41:16 UTC

Update Date

2022-08-12 20:09:13 UTC

Metabolite ID

MMDBc0055070

Metabolite Identification

Common Name

(S)-malyl N-acetyl-alpha-D-glucosaminide

Description

(S)-malyl N-acetyl-alpha-D-glucosaminide(2-), also known as glcnac-mal(2-) or malyl-N-acetyl-D-glucosamine, 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. Based on a literature review very few articles have been published on (S)-malyl N-acetyl-alpha-D-glucosaminide(2-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221412D          

 29 29  0  0  1  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  4  0  0  0
  5  2  1  0  0  0  0
  6  3  1  1  0  0  0
  7  2  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  4  2  0  0  0  0
  8 13  1  6  0  0  0
 14  3  1  0  0  0  0
 15  4  1  0  0  0  0
 16  7  2  0  0  0  0
 17  7  1  0  0  0  0
  9 18  1  6  0  0  0
 10 19  1  6  0  0  0
 20 11  2  0  0  0  0
 21 11  1  0  0  0  0
  5 22  1  6  0  0  0
 12 22  1  6  0  0  0
 23  6  1  0  0  0  0
 23 12  1  0  0  0  0
  5 24  1  6  0  0  0
  6 25  1  6  0  0  0
  8 26  1  1  0  0  0
  9 27  1  1  0  0  0
 10 28  1  6  0  0  0
 12 29  1  1  0  0  0
M  CHG  2  15  -1  17  -1
M  END


  Mrv1652306172221412D          

 29 29  0  0  1  0            999 V2000
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  4  0  0  0
  5  2  1  0  0  0  0
  6  3  1  1  0  0  0
  7  2  1  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  4  2  0  0  0  0
  8 13  1  6  0  0  0
 14  3  1  0  0  0  0
 15  4  1  0  0  0  0
 16  7  2  0  0  0  0
 17  7  1  0  0  0  0
  9 18  1  6  0  0  0
 10 19  1  6  0  0  0
 20 11  2  0  0  0  0
 21 11  1  0  0  0  0
  5 22  1  6  0  0  0
 12 22  1  6  0  0  0
 23  6  1  0  0  0  0
 23 12  1  0  0  0  0
  5 24  1  6  0  0  0
  6 25  1  6  0  0  0
  8 26  1  1  0  0  0
  9 27  1  1  0  0  0
 10 28  1  6  0  0  0
 12 29  1  1  0  0  0
M  CHG  2  15  -1  17  -1
M  END
> <DATABASE_ID>
MMDBc0055070

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H19NO10/c1-4(15)13-8-10(19)9(18)6(3-14)23-12(8)22-5(11(20)21)2-7(16)17/h5-6,8-10,12,14,18-19H,2-3H2,1H3,(H,13,15)(H,16,17)(H,20,21)/p-2/t5-,6+,8+,9+,10+,12-/m0/s1

> <INCHI_KEY>
COBMRTSHZAUOCY-BVKYVCSXSA-L

> <FORMULA>
C12H17NO10

> <MOLECULAR_WEIGHT>
335.266

> <EXACT_MASS>
335.086342911

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.434852740446786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
-2

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-carboxy-3-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}propanoate

> <JCHEM_LOGP>
-2.3529081403333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.035381945431244

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.357307502113465

> <JCHEM_PKA_STRONGEST_BASIC>
1.2198369715614725

> <JCHEM_POLAR_SURFACE_AREA>
191.99999999999997

> <JCHEM_REFRACTIVITY>
90.2989

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-carboxy-3-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -4.001   6.930   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O-1
HETATM   18  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.001  10.010   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   24  H   UNK     0       1.334   3.850   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.000  10.780   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.001   8.470   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0      -2.667  10.780   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0      -1.334   8.470   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.667   6.160   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2    5    7                                                       
CONECT    3    6   14                                                       
CONECT    4    1   13   15                                                  
CONECT    5    2   11   22   24                                             
CONECT    6    3    9   23   25                                             
CONECT    7    2   16   17                                                  
CONECT    8   10   12   13   26                                             
CONECT    9    6   10   18   27                                             
CONECT   10    8    9   19   28                                             
CONECT   11    5   20   21                                                  
CONECT   12    8   22   23   29                                             
CONECT   13    4    8                                                       
CONECT   14    3                                                            
CONECT   15    4                                                            
CONECT   16    7                                                            
CONECT   17    7                                                            
CONECT   18    9                                                            
CONECT   19   10                                                            
CONECT   20   11                                                            
CONECT   21   11                                                            
CONECT   22    5   12                                                       
CONECT   23    6   12                                                       
CONECT   24    5                                                            
CONECT   25    6                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   12                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

Synonyms

Value	Source
(S)-Malyl N-acetyl-alpha-D-glucosaminide	ChEBI
GlcNAc-mal(2-)	ChEBI
Malyl N-acetyl-alpha-D-glucosaminide(2-)	ChEBI
Malyl-N-acetyl-D-glucosamine	ChEBI
(S)-Malyl N-acetyl-a-D-glucosaminide	Generator
(S)-Malyl N-acetyl-α-D-glucosaminide	Generator
Malyl N-acetyl-a-D-glucosaminide(2-)	Generator
Malyl N-acetyl-α-D-glucosaminide(2-)	Generator
(S)-Malyl N-acetyl-a-D-glucosaminide(2-)	Generator
(S)-Malyl N-acetyl-α-D-glucosaminide(2-)	Generator

Molecular Formula

C₁₂H₁₇NO₁₀

Average Mass

335.266

Monoisotopic Mass

335.086342911

IUPAC Name

(3S)-3-carboxy-3-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}propanoate

Traditional Name

(3S)-3-carboxy-3-{[(2R,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(1-oxidoethylidene)amino]oxan-2-yl]oxy}propanoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H19NO10/c1-4(15)13-8-10(19)9(18)6(3-14)23-12(8)22-5(11(20)21)2-7(16)17/h5-6,8-10,12,14,18-19H,2-3H2,1H3,(H,13,15)(H,16,17)(H,20,21)/p-2/t5-,6+,8+,9+,10+,12-/m0/s1

InChI Key

COBMRTSHZAUOCY-BVKYVCSXSA-L

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

Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
N-acyl-alpha-hexosamine
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Sugar acid
Heterocyclic fatty acid
Hydroxy fatty acid
Fatty acyl
Fatty acid
Dicarboxylic acid or derivatives
Oxane
Monosaccharide
Acetamide
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Acetal
Organopnictogen compound
Organic nitrogen compound
Primary alcohol
Carbonyl group
Organonitrogen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

carbohydrate acid derivative anion (CHEBI:64870 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2.4	ChemAxon
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	1.22	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	192 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	90.3 m³·mol⁻¹	ChemAxon
Polarizability	29.43 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

Not Available

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	3	Human ; Human feces

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

28184702

KEGG Compound ID

Not Available

BioCyc ID

CPD8J2-1

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57339290

PDB ID

Not Available

ChEBI ID

64870

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 (S)-malyl N-acetyl-alpha-D-glucosaminide (MMDBc0055070)

MOL for #<Metabolite:0x00007fdb4cb64a48>

3D MOL for #<Metabolite:0x00007fdb4cb64a48>

3D SDF for #<Metabolite:0x00007fdb4cb64a48>

3D-SDF for #<Metabolite:0x00007fdb4cb64a48>

PDB for #<Metabolite:0x00007fdb4cb64a48>

3D PDB for #<Metabolite:0x00007fdb4cb64a48>

SMILES for #<Metabolite:0x00007fdb4cb64a48>

INCHI for #<Metabolite:0x00007fdb4cb64a48>

Structure for #<Metabolite:0x00007fdb4cb64a48>

3D Structure for #<Metabolite:0x00007fdb4cb64a48>