MiMeDB: Showing metabocard for (S)-malyl alpha-D-glucosaminide (MMDBc0055069)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:41:15 UTC

Update Date

2022-08-12 20:09:13 UTC

Metabolite ID

MMDBc0055069

Metabolite Identification

Common Name

(S)-malyl alpha-D-glucosaminide

Description

(S)-malyl alpha-D-glucosaminide(1-), also known as GLCN-mal(1-) or malyl-D-glucosamine, belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars. Based on a literature review very few articles have been published on (S)-malyl alpha-D-glucosaminide(1-).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221412D          

 26 26  0  0  1  0            999 V2000
    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
   -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
    2.1434    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
  3  1  1  0  0  0  0
  4  2  1  1  0  0  0
  5  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
  6 11  1  6  0  0  0
 12  2  1  0  0  0  0
 13  5  2  0  0  0  0
 14  5  1  0  0  0  0
  7 15  1  6  0  0  0
  8 16  1  6  0  0  0
 17  9  2  0  0  0  0
 18  9  1  0  0  0  0
  3 19  1  6  0  0  0
 10 19  1  6  0  0  0
 20  4  1  0  0  0  0
 20 10  1  0  0  0  0
  3 21  1  6  0  0  0
  4 22  1  6  0  0  0
  6 23  1  1  0  0  0
  7 24  1  1  0  0  0
  8 25  1  6  0  0  0
 10 26  1  1  0  0  0
M  CHG  1  14  -1
M  END


  Mrv1652306172221412D          

 26 26  0  0  1  0            999 V2000
    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
   -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
    2.1434    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
  3  1  1  0  0  0  0
  4  2  1  1  0  0  0
  5  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
  6 11  1  6  0  0  0
 12  2  1  0  0  0  0
 13  5  2  0  0  0  0
 14  5  1  0  0  0  0
  7 15  1  6  0  0  0
  8 16  1  6  0  0  0
 17  9  2  0  0  0  0
 18  9  1  0  0  0  0
  3 19  1  6  0  0  0
 10 19  1  6  0  0  0
 20  4  1  0  0  0  0
 20 10  1  0  0  0  0
  3 21  1  6  0  0  0
  4 22  1  6  0  0  0
  6 23  1  1  0  0  0
  7 24  1  1  0  0  0
  8 25  1  6  0  0  0
 10 26  1  1  0  0  0
M  CHG  1  14  -1
M  END
> <DATABASE_ID>
MMDBc0055069

> <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(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H17NO9/c11-6-8(16)7(15)4(2-12)20-10(6)19-3(9(17)18)1-5(13)14/h3-4,6-8,10,12,15-16H,1-2,11H2,(H,13,14)(H,17,18)/p-1/t3-,4+,6+,7+,8+,10-/m0/s1

> <INCHI_KEY>
DFSUVSNIIHLGAX-NKQVSKEESA-M

> <FORMULA>
C10H16NO9

> <MOLECULAR_WEIGHT>
294.237

> <EXACT_MASS>
294.083054679

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.775034647244816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-5.338712315126803

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.921937744463434

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0912003835201665

> <JCHEM_PKA_STRONGEST_BASIC>
8.126892011667492

> <JCHEM_POLAR_SURFACE_AREA>
182.59999999999997

> <JCHEM_REFRACTIVITY>
69.7831

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

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

> <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       1.334   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -4.001   6.930   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.667   3.080   0.000  0.00  0.00           O-1
HETATM   15  O   UNK     0      -1.334  11.550   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.001  10.010   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM   21  H   UNK     0       1.334   3.850   0.000  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.000  10.780   0.000  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.001   8.470   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.667  10.780   0.000  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.334   8.470   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.667   6.160   0.000  0.00  0.00           H+0
CONECT    1    3    5                                                       
CONECT    2    4   12                                                       
CONECT    3    1    9   19   21                                             
CONECT    4    2    7   20   22                                             
CONECT    5    1   13   14                                                  
CONECT    6    8   10   11   23                                             
CONECT    7    4    8   15   24                                             
CONECT    8    6    7   16   25                                             
CONECT    9    3   17   18                                                  
CONECT   10    6   19   20   26                                             
CONECT   11    6                                                            
CONECT   12    2                                                            
CONECT   13    5                                                            
CONECT   14    5                                                            
CONECT   15    7                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18    9                                                            
CONECT   19    3   10                                                       
CONECT   20    4   10                                                       
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    6                                                            
CONECT   24    7                                                            
CONECT   25    8                                                            
CONECT   26   10                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

Synonyms

Value	Source
(S)-Malyl alpha-D-glucosaminide	ChEBI
GLCN-Mal(1-)	ChEBI
Malyl-D-glucosamine	ChEBI
(S)-Malyl a-D-glucosaminide	Generator
(S)-Malyl α-D-glucosaminide	Generator
(S)-Malyl a-D-glucosaminide(1-)	Generator
(S)-Malyl α-D-glucosaminide(1-)	Generator

Molecular Formula

C₁₀H₁₆NO₉

Average Mass

294.237

Monoisotopic Mass

294.083054679

IUPAC Name

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

Traditional Name

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

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(O)=O

InChI Identifier

InChI=1S/C10H17NO9/c11-6-8(16)7(15)4(2-12)20-10(6)19-3(9(17)18)1-5(13)14/h3-4,6-8,10,12,15-16H,1-2,11H2,(H,13,14)(H,17,18)/p-1/t3-,4+,6+,7+,8+,10-/m0/s1

InChI Key

DFSUVSNIIHLGAX-NKQVSKEESA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Aminoglycosides

Alternative Parents

Substituents

Aminoglycoside core
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Heterocyclic fatty acid
Hydroxy fatty acid
Sugar acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Monosaccharide
Oxane
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid salt
Amino acid
Secondary alcohol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Primary alcohol
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Alcohol
Organic salt
Carbonyl group
Organic nitrogen compound
Primary aliphatic amine
Primary amine
Amine
Organonitrogen compound
Organic anion
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

organic molecular entity (CHEBI:64871 )
carbohydrate acid derivative anion (CHEBI:64871 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-5.3	ChemAxon
pKa (Strongest Acidic)	3.09	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	182.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.78 m³·mol⁻¹	ChemAxon
Polarizability	25.78 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	Deposition Date	View
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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0015218	(S)-malyl N-acetyl-alpha-D-glucosaminide	(S)-malyl alpha-D-glucosaminide	N-acetyl-alpha-D-glucosaminyl L-malate deacetylase 1	Deacetylation	RHEA	34755880

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

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

28184703

KEGG Compound ID

Not Available

BioCyc ID

CPD8J2-2

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

57339292

PDB ID

Not Available

ChEBI ID

64871

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 alpha-D-glucosaminide (MMDBc0055069)

MOL for #<Metabolite:0x00007f5a98d50d50>

3D MOL for #<Metabolite:0x00007f5a98d50d50>

3D SDF for #<Metabolite:0x00007f5a98d50d50>

3D-SDF for #<Metabolite:0x00007f5a98d50d50>

PDB for #<Metabolite:0x00007f5a98d50d50>

3D PDB for #<Metabolite:0x00007f5a98d50d50>

SMILES for #<Metabolite:0x00007f5a98d50d50>

INCHI for #<Metabolite:0x00007f5a98d50d50>

Structure for #<Metabolite:0x00007f5a98d50d50>

3D Structure for #<Metabolite:0x00007f5a98d50d50>