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Showing metabocard for (-)-N-Acetylneuraminic acid (HMDB0341204)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2022-09-09 19:40:53 UTC
Update Date2022-09-22 18:34:39 UTC
HMDB IDHMDB0341204
Secondary Accession NumbersNone
Metabolite Identification
Common Name(-)-N-Acetylneuraminic acid
Description(-)-N-Acetylneuraminic acid belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. Based on a literature review a significant number of articles have been published on (-)-N-Acetylneuraminic acid.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for HMDB0341204 ((-)-N-Acetylneuraminic acid)


  Mrv1652309092222192D          

 26 26  0  0  1  0            999 V2000
    2.1434    2.8875    0.0000 H   0  0  0  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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7111   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  4  0  0  0
 21 23  1  0  0  0  0
 12 24  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
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3D MOL for HMDB0341204 ((-)-N-Acetylneuraminic acid)

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3D SDF for HMDB0341204 ((-)-N-Acetylneuraminic acid)

  Mrv1652309092222192D          

 26 26  0  0  1  0            999 V2000
    2.1434    2.8875    0.0000 H   0  0  0  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
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7111   -0.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -0.4887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    0.9185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
  9 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  6  0  0  0
 20 21  2  0  0  0  0
 21 22  1  4  0  0  0
 21 23  1  0  0  0  0
 12 24  1  6  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341204

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]C(O)(CO)C([H])(O)C1([H])O[C@@](O)(CC([H])(O)[C@@]1([H])N=C(C)O)C(O)=O

> <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+/m1/s1

> <INCHI_KEY>
SQVRNKJHWKZAKO-PFLSSZHQSA-N

> <FORMULA>
C11H19NO9

> <MOLECULAR_WEIGHT>
309.271

> <EXACT_MASS>
309.105981196

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
28.323419725195112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-3.114727239269535

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.675319064267648

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.0206585777382724

> <JCHEM_PKA_STRONGEST_BASIC>
2.0937519590170552

> <JCHEM_POLAR_SURFACE_AREA>
180.26999999999998

> <JCHEM_REFRACTIVITY>
64.3031

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for HMDB0341204 ((-)-N-Acetylneuraminic acid)
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PDB for HMDB0341204 ((-)-N-Acetylneuraminic acid)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  H   UNK     0       4.001   5.390   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0       1.334   5.390   0.000  0.00  0.00           H+0
HETATM    8  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0       0.000   3.080   0.000  0.00  0.00           H+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.194  -1.447   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+0
HETATM   17  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0       1.334   0.770   0.000  0.00  0.00           H+0
HETATM   20  N   UNK     0      -1.334   2.310   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.184   0.267   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.174  -0.912   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.711   1.715   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    6                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4                                                            
CONECT    6    2    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10   11   18                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   24                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15    9   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   12   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   52    0
END

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3D PDB for HMDB0341204 ((-)-N-Acetylneuraminic acid)
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SMILES for HMDB0341204 ((-)-N-Acetylneuraminic acid)
[H]C(O)(CO)C([H])(O)C1([H])O[C@@](O)(CC([H])(O)[C@@]1([H])N=C(C)O)C(O)=O
Download
INCHI for HMDB0341204 ((-)-N-Acetylneuraminic acid)
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+/m1/s1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
(-)-N-AcetylneuraminateGenerator
Chemical FormulaC11H19NO9
Average Molecular Weight309.271
Monoisotopic Molecular Weight309.105981196
IUPAC Name(2S,5R)-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Traditional Name(2S,5R)-2,4-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H]C(O)(CO)C([H])(O)C1([H])O[C@@](O)(CC([H])(O)[C@@]1([H])N=C(C)O)C(O)=O
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+/m1/s1
InChI KeySQVRNKJHWKZAKO-PFLSSZHQSA-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.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbohydrates and carbohydrate conjugates  
Direct ParentN-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 FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP-3.1ChemAxon
pKa (Strongest Acidic)3.02ChemAxon
pKa (Strongest Basic)2.09ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area180.27 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.3 m³·mol⁻¹ChemAxon
Polarizability28.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties
Predicted Kovats Retention Indices
Not Available
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
    • 

  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation  details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound49819355  
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simon-Manso Y, Marupaka R, Yan X, Liang Y, Telu KH, Mirokhin Y, Stein SE: Mass Spectrometry Fingerprints of Small-Molecule Metabolites in Biofluids: Building a Spectral Library of Recurrent Spectra for Urine Analysis. Anal Chem. 2019 Sep 17;91(18):12021-12029. doi: 10.1021/acs.analchem.9b02977. Epub 2019 Aug 30. [PubMed:31424920  ]