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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2022-09-09 19:32:26 UTC

Update Date

2022-09-22 18:35:05 UTC

HMDB ID

HMDB0341180

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetylneuraminic acid methyl ester 1

Description

N-[4,6-dihydroxy-6-(methoxycarbonyl)-2-(1,2,3-trihydroxypropyl)oxan-3-yl]ethanimidic acid belongs to the class of organic compounds known as n-acylneuraminic acids and derivatives. These are neuraminic acids (or derivatives thereof) carrying an N-acyl substituent. N-[4,6-dihydroxy-6-(methoxycarbonyl)-2-(1,2,3-trihydroxypropyl)oxan-3-yl]ethanimidic acid is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306031608242D          

 22 22  0  0  0  0            999 V2000
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788    2.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  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
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   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
    2.1434   -0.4125    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
    0.1842    1.8695    0.0000 C   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
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6283    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    2.6447    0.0000 O   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
  5  1  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 12  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13  5  2  0  0  0  0
 13  8  1  4  0  0  0
 14  4  1  0  0  0  0
 15  5  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  9  1  0  0  0  0
 19 11  2  0  0  0  0
 20 12  1  0  0  0  0
 21  2  1  0  0  0  0
 21 11  1  0  0  0  0
 22 10  1  0  0  0  0
 22 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0341180

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1(O)CC(O)C(N=C(C)O)C(O1)C(O)C(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(20,11(19)21-2)22-10(8)9(18)7(17)4-14/h6-10,14,16-18,20H,3-4H2,1-2H3,(H,13,15)

> <INCHI_KEY>
BKZQMWNJESHHSA-UHFFFAOYSA-N

> <FORMULA>
C12H21NO9

> <MOLECULAR_WEIGHT>
323.298

> <EXACT_MASS>
323.12163126

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
29.842424053966973

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[4,6-dihydroxy-6-(methoxycarbonyl)-2-(1,2,3-trihydroxypropyl)oxan-3-yl]ethanimidic acid

> <ALOGPS_LOGP>
-2.17

> <JCHEM_LOGP>
-2.5984393359999993

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.563941583102423

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.673255783013772

> <JCHEM_PKA_STRONGEST_BASIC>
2.2137331058341085

> <JCHEM_POLAR_SURFACE_AREA>
169.26999999999998

> <JCHEM_REFRACTIVITY>
69.07220000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[4,6-dihydroxy-6-(methoxycarbonyl)-2-(1,2,3-trihydroxypropyl)oxan-3-yl]ethanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-JUN-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-JUN-16         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.387   5.204   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.173   3.222   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       0.870   4.937   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   21                                                            
CONECT    3    6   12                                                       
CONECT    4    7   14                                                       
CONECT    5    1   13   15                                                  
CONECT    6    3    8   16                                                  
CONECT    7    4    9   17                                                  
CONECT    8    6   10   13                                                  
CONECT    9    7   10   18                                                  
CONECT   10    8    9   22                                                  
CONECT   11   12   19   21                                                  
CONECT   12    3   11   20   22                                             
CONECT   13    5    8                                                       
CONECT   14    4                                                            
CONECT   15    5                                                            
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    9                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21    2   11                                                       
CONECT   22   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-[4,6-Dihydroxy-6-(methoxycarbonyl)-2-(1,2,3-trihydroxypropyl)oxan-3-yl]ethanimidate	Generator

Chemical Formula

C₁₂H₂₁NO₉

Average Molecular Weight

323.298

Monoisotopic Molecular Weight

323.12163126

IUPAC Name

N-[4,6-dihydroxy-6-(methoxycarbonyl)-2-(1,2,3-trihydroxypropyl)oxan-3-yl]ethanimidic acid

Traditional Name

N-[4,6-dihydroxy-6-(methoxycarbonyl)-2-(1,2,3-trihydroxypropyl)oxan-3-yl]ethanimidic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1(O)CC(O)C(N=C(C)O)C(O1)C(O)C(O)CO

InChI Identifier

InChI=1S/C12H21NO9/c1-5(15)13-8-6(16)3-12(20,11(19)21-2)22-10(8)9(18)7(17)4-14/h6-10,14,16-18,20H,3-4H2,1-2H3,(H,13,15)

InChI Key

BKZQMWNJESHHSA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylneuraminic acids and derivatives. These are neuraminic acids (or derivatives thereof) 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 and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-2.2	ALOGPS
logP	-2.6	ChemAxon
logS	-0.66	ALOGPS
pKa (Strongest Acidic)	5.67	ChemAxon
pKa (Strongest Basic)	2.21	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	169.27 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.07 m³·mol⁻¹	ChemAxon
Polarizability	29.84 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

Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylneuraminic acid methyl ester 1 10V, Negative-QTOF	splash10-01po-3492000000-2a2d20cb09cb5d4a009a	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylneuraminic acid methyl ester 1 20V, Negative-QTOF	splash10-0udi-3910000000-d6e34aa22795b31e70f4	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylneuraminic acid methyl ester 1 40V, Negative-QTOF	splash10-0a4i-9400000000-ddfb623ed7bb1b8ef267	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylneuraminic acid methyl ester 1 10V, Positive-QTOF	splash10-0c00-1079000000-794c28d7e3a6b9dd764b	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylneuraminic acid methyl ester 1 20V, Positive-QTOF	splash10-03di-7092000000-9c08b1482a236346495f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylneuraminic acid methyl ester 1 40V, Positive-QTOF	splash10-03di-9230000000-3941876a9542240123f3	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3383006

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Neto FC, Raftery D: Expanding Urinary Metabolite Annotation through Integrated Mass Spectral Similarity Networking. Anal Chem. 2021 Sep 7;93(35):12001-12010. doi: 10.1021/acs.analchem.1c02041. Epub 2021 Aug 26. [PubMed:34436864 ]

Showing metabocard for N-Acetylneuraminic acid methyl ester 1 (HMDB0341180)

MOL for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

3D MOL for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

3D SDF for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

3D-SDF for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

PDB for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

3D PDB for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

SMILES for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

INCHI for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

Structure for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

3D Structure for HMDB0341180 (N-Acetylneuraminic acid methyl ester 1)

Predicted Kovats Retention Indices

MS/MS Spectra