MiMeDB: Showing metabocard for N-acetylneuraminate (MMDBc0031157)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:37:40 UTC

Update Date

2022-08-31 17:58:58 UTC

Metabolite ID

MMDBc0031157

Metabolite Identification

Common Name

N-acetylneuraminate

Description

A ketoaldonate that is the conjugate base of N-acetylneuraminic acid, obtained by deprotonation of the carboxy group

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07171211592D          
 
 22 22  0  0  1  0            999 V2000
   14.2278  -12.5962    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.2278  -13.4212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9432  -12.1889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5123  -12.1889    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.9432  -13.8353    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.5123  -13.8353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6517  -12.5962    0.0000 C   0  0  3  0  0  0  0  0  0  0  0  0
   13.5157  -11.3638    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.8002  -12.5962    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6517  -13.4212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9432  -14.6568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5157  -14.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2337  -12.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4424  -12.8084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8002  -10.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2278  -10.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8071  -15.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2242  -15.0608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0312  -12.2196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0111  -11.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8002  -10.1281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5154  -13.0075    0.0000 H   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  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  1  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  7 13  1  4  0  0  0
  7 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  1  0  0  0
 12 17  1  0  0  0  0
 12 18  2  0  0  0  0
 13 19  1  0  0  0  0
 13 20  2  0  0  0  0
 15 21  1  0  0  0  0
  7 10  1  0  0  0  0
  1 22  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031157

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11?/m0/s1

> <INCHI_KEY>
SQVRNKJHWKZAKO-LUWBGTNYSA-N

> <FORMULA>
C11H19NO9

> <MOLECULAR_WEIGHT>
309.2699

> <EXACT_MASS>
309.105981211

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
28.074331661709863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

> <ALOGPS_LOGP>
-2.78

> <JCHEM_LOGP>
-3.5639375190000004

> <ALOGPS_LOGS>
-0.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.107002534745776

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9967961479730394

> <JCHEM_PKA_STRONGEST_BASIC>
-0.37947152477492263

> <JCHEM_POLAR_SURFACE_AREA>
176.77999999999997

> <JCHEM_REFRACTIVITY>
63.781400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
NeuAc

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUL-12         0                                  
HETATM    1  C   UNK     0      26.559 -23.513   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.559 -25.053   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      27.894 -22.753   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      25.223 -22.753   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.894 -25.826   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      25.223 -25.826   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      29.217 -23.513   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.229 -21.212   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      23.894 -23.513   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      29.217 -25.053   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      27.894 -27.359   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      25.229 -27.353   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      30.303 -22.420   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      30.693 -23.909   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      23.894 -20.439   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      26.559 -20.439   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      23.907 -28.120   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      26.552 -28.113   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      31.792 -22.810   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      29.887 -20.938   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      23.894 -18.906   0.000  0.00  0.00           O+0
HETATM   22  H   UNK     0      25.229 -24.281   0.000  0.00  0.00           H+0
CONECT    1    2    3    4   22                                             
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13   14   10                                             
CONECT    8    4   15   16                                                  
CONECT    9    4                                                            
CONECT   10    5    7                                                       
CONECT   11    5                                                            
CONECT   12    6   17   18                                                  
CONECT   13    7   19   20                                                  
CONECT   14    7                                                            
CONECT   15    8   21                                                       
CONECT   16    8                                                            
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
CONECT   21   15                                                            
CONECT   22    1                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

Synonyms

Value	Source
5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid	ChEBI
Aceneuramic acid	ChEBI
Acide aceneuramique	ChEBI
Acidium aceneuramicum	ChEBI
Acido aceneuramico	ChEBI
Neu5ac	ChEBI
NeuAc	ChEBI
O-Sialic acid	ChEBI
N-Acetylneuraminic acid	Kegg
5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate	Generator
Aceneuramate	Generator
O-Sialate	Generator
Acid, N-acetylneuraminic	MeSH
N Acetylneuraminic acid	MeSH
Sialic acid	MeSH
Acid, sialic	MeSH

Molecular Formula

C₁₁H₁₉NO₉

Average Mass

309.2699

Monoisotopic Mass

309.105981211

IUPAC Name

(4S,5R,6R)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

Traditional Name

NeuAc

CAS Registry Number

131-48-6

SMILES

[H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)CO

InChI Identifier

InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11?/m0/s1

InChI Key

SQVRNKJHWKZAKO-LUWBGTNYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminic acids

Alternative Parents

Substituents

N-acylneuraminic acid
Neuraminic acid
C-glucuronide
C-glycosyl compound
Glycosyl compound
Alpha-hydroxy acid
Pyran
Hydroxy acid
Oxane
Acetamide
Carboxamide group
Hemiacetal
Secondary carboxylic acid amide
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organopnictogen compound
Primary alcohol
Organic oxide
Carbonyl group
Organonitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

N-acetylneuraminic acids (CHEBI:17012 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	227 g/L	ALOGPS
logP	-2.8	ALOGPS
logP	-3.6	ChemAxon
logS	-0.13	ALOGPS
pKa (Strongest Acidic)	3	ChemAxon
pKa (Strongest Basic)	-0.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	176.78 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.78 m³·mol⁻¹	ChemAxon
Polarizability	28.07 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_2_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-1092000000-ca2f76604846382a3032	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kc-6190000000-7e304e9fa3125067d352	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-08fu-9240000000-65d03a6c6f60a71416c6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-074j-4961000000-bc80694ae9687db9a365	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9210000000-c1d9f41a64bc464147dd	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-a1d857dc5ad7118647b3	2015-09-15	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	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	Proteobacteria	51	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Pig ; Chicken	Unknown
Bacteria	Firmicutes	20	Human ; Human feces; Cattle
Bacteria	Fusobacteria	1	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

C00019584

Chemspider ID

Not Available

KEGG Compound ID

C00270

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-acetylneuraminic_acid

METLIN ID

Not Available

PubChem Compound

439197

PDB ID

Not Available

ChEBI ID

17012

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-acetylneuraminate (MMDBc0031157)

MOL for #<Metabolite:0x00007fdb50a60508>

3D MOL for #<Metabolite:0x00007fdb50a60508>

3D SDF for #<Metabolite:0x00007fdb50a60508>

3D-SDF for #<Metabolite:0x00007fdb50a60508>

PDB for #<Metabolite:0x00007fdb50a60508>

3D PDB for #<Metabolite:0x00007fdb50a60508>

SMILES for #<Metabolite:0x00007fdb50a60508>

INCHI for #<Metabolite:0x00007fdb50a60508>

Structure for #<Metabolite:0x00007fdb50a60508>

3D Structure for #<Metabolite:0x00007fdb50a60508>