MiMeDB: Showing metabocard for N-Acetylneuraminic acid (MMDBc0000078)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:29:34 UTC

Update Date

2022-08-30 23:30:32 UTC

Metabolite ID

MMDBc0000078

Metabolite Identification

Common Name

N-Acetylneuraminic acid

Description

N-Acetylneuraminic acid (NeuAc) (CAS: 131-48-6), also known as sialic acid, is an acetyl derivative of the amino sugar neuraminic acid. It occurs in many glycoproteins, glycolipids, and polysaccharides in both mammals and bacteria. The most abundant sialic acid, NeuAc, is synthesized in vivo from N-acetylated D-mannosamine (ManNAc) or D-glucosamine (GlcNAc). NeuAc and its activated form, CMP-NeuAc, are biosynthesized in five consecutive reactions that form the intermediates UDP-N-acetylglucosamine (UDP-GlcNAc), N-acetylmannosamine (ManNAc), ManNAc 6-phosphate, NeuAc 9-phosphate, and CMP-NeuAc. CMP-NeuAc is transported into the Golgi apparatus and, with the aid of specific sialyltransferases, added onto nonreducing positions on oligosaccharide chains of glycoproteins and glycolipids. NeuAc is widely distributed throughout human tissues and found in several fluids, including serum, cerebrospinal fluid, saliva, urine, amniotic fluid, and breast milk. It is found in high levels in the brain, adrenal glands, and the heart. Serum and urine levels of the free acid are elevated in individuals suffering from renal failure. Serum and saliva Neu5Ac levels are also elevated in alcoholics. A genetic disorder known as Salla disease or infantile NeuAc storage disease is also characterized by high serum and urine levels of this compound. The negative charge is responsible for the slippery feel of saliva and mucins coating the body's organs. This particular sialic acid is known to act as a "decoy"" for invading pathogens. Along with involvement in preventing infections (mucus associated with mucous membranes — mouth, nose, GI, respiratory tract), Neu5Ac acts as a receptor for influenza viruses, allowing attachment to mucous cells via hemagglutinin (an early step in acquiring influenzavirus infection). NeuAc is also becoming known as an agent necessary for mediating ganglioside distribution and structures in the brain. Sialic acid (SA) is an N-acetylated derivative of neuraminic acid that is an abundant terminal monosaccharide of glycoconjugates. Normal human serum SA is largely bound to glycoproteins or glycolipids (total sialic acid (TSA): 1.5-2.5 mmol/L), with small amounts of free SA (1-3 umol/L). Negatively charged SA units stabilize glycoprotein conformation in cell surface receptors to increase cell rigidity. This enables signal recognition and adhesion to ligands, antibodies, enzymes, and microbes. SA residues are antigenic determinant residues in carbohydrate chains of glycolipids and glycoproteins, chemical messengers in tissue and body fluids, and may regulate glomeruli basement membrane permeability. Sialic acids are structurally unique nine-carbon keto sugars occupying the interface between the host and commensal or pathogenic microorganisms. An important function of host sialic acid is to regulate innate immunity. Sialic acid is the moiety most actively recycled for metabolic purposes in the salvage pathways in glycosphingolipid metabolism. Sialic acid is indispensable for the neuritogenic activities of ganglioside constituents which are unique in that a sialic acid directly binds to the glucose of the cerebroside, they are mutually connected in tandem, and some are located in the internal parts of the sugar chain. Sialylation (sialic acid linked to galactose, N-acetylgalactosamine, or another sialic acid) represents one of the most frequently occurring terminations of the oligosaccharide chains of glycoproteins and glycolipids. The biosynthesis of the various linkages is mediated by the different members of the sialyltransferase family (PMID: 11425186 , 11287396 , 12770781 , 16624269 , 12510390 , 15007099 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0000230
     RDKit          3D
N-Acetylneuraminic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -1.0141    4.2332    0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    2.9295   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935    2.9435   -1.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    1.6907    0.6069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534    0.4325   -0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2482   -0.3255    0.7808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5349    0.0538    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523   -1.8044    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513   -2.3136    0.4313 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0298   -2.1603    1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385   -3.7574    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4915   -4.1284   -0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248   -4.7091    0.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815   -1.6126   -0.5793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549   -0.3202   -0.1435 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0730    0.4816   -0.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7635    0.5770   -2.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4795   -0.0537   -0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7570   -0.1366    0.6588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    0.9931   -1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7516    0.6110   -1.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8911    4.8974    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0007    4.1050    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687    4.7041    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5502    1.7439    1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6964    0.6178   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -0.0009    1.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6110   -0.1146   -0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -2.2560    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -2.2165   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.1925    2.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -5.4132    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -0.3723    0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660    1.5185   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -0.2874   -2.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -1.0332   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347   -0.0119    0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257    1.9388   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    1.1162   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8606   -0.3671   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  1
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  1
 16 34  1  1
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END


  Mrv1652311131907572D          

 22 22  0  0  0  0            999 V2000
 9985.8394 9985.0642    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9986.5531 9985.4756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9987.2688 9985.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.9824 9985.4756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9986.5531 9986.3007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.8394 9984.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9984.4098 9984.2391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6953 9983.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.9808 9984.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6953 9983.0005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9982.9788 9985.0642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9984.4098 9987.5383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6953 9987.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.1243 9987.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.1243 9987.1258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9985.1243 9984.6506    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9984.4098 9986.7122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9983.6964 9986.3003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.6964 9985.4764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9984.4098 9985.0646    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9985.1233 9985.4764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9985.1233 9986.3003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  1  0  0  0
  2  3  1  0  0  0  0
  2  5  1  6  0  0  0
  3  4  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 22  1  0  0  0  0
  1 21  1  0  0  0  0
 21 16  1  6  0  0  0
 20  7  1  6  0  0  0
 19 11  1  1  0  0  0
 17 12  1  0  0  0  0
 17 15  1  6  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000078

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@]1(O[C@@](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-PFQGKNLYSA-N

> <FORMULA>
C11H19NO9

> <MOLECULAR_WEIGHT>
309.2699

> <EXACT_MASS>
309.105981211

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
27.818468332190793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,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>
11.10700253474434

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9966581465692994

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3430861642982186

> <JCHEM_POLAR_SURFACE_AREA>
176.78

> <JCHEM_REFRACTIVITY>
63.7814

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-neu5ac

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0000230
     RDKit          3D
N-Acetylneuraminic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -1.0141    4.2332    0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    2.9295   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935    2.9435   -1.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    1.6907    0.6069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534    0.4325   -0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2482   -0.3255    0.7808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5349    0.0538    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523   -1.8044    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513   -2.3136    0.4313 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0298   -2.1603    1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385   -3.7574    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4915   -4.1284   -0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248   -4.7091    0.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815   -1.6126   -0.5793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549   -0.3202   -0.1435 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0730    0.4816   -0.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7635    0.5770   -2.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4795   -0.0537   -0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7570   -0.1366    0.6588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    0.9931   -1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7516    0.6110   -1.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8911    4.8974    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0007    4.1050    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687    4.7041    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5502    1.7439    1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6964    0.6178   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -0.0009    1.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6110   -0.1146   -0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -2.2560    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -2.2165   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.1925    2.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -5.4132    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -0.3723    0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660    1.5185   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -0.2874   -2.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -1.0332   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347   -0.0119    0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257    1.9388   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    1.1162   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8606   -0.3671   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  1
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  1
 16 34  1  1
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 13-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-19         0                                  
HETATM    1  C   UNK     0    8640.2348638.786   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8641.5668639.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8642.9028638.786   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8644.2348639.554   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8641.5668641.095   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8640.2348637.246   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0    8637.5658637.246   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0    8636.2318636.474   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8634.8978637.246   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8636.2318634.934   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8634.8948638.786   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    8637.5658643.405   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8636.2318644.175   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    8638.8998644.175   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    8638.8998642.635   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0    8638.8998638.014   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0    8637.5658641.863   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8636.2338641.094   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8636.2338639.556   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8637.5658638.787   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8638.8978639.556   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8638.8978641.094   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    1                                                            
CONECT    7    8   20                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   19                                                            
CONECT   12   13   14   17                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   17                                                            
CONECT   16   21                                                            
CONECT   17   18   22   12   15                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   11                                                  
CONECT   20   19   21    7                                                  
CONECT   21   20   22    1   16                                             
CONECT   22   17   21                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0000230
HETATM    1  C1  UNL     1      -1.014   4.233   0.599  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.273   2.930  -0.023  1.00  0.00           C  
HETATM    3  O1  UNL     1      -1.794   2.944  -1.189  1.00  0.00           O  
HETATM    4  N1  UNL     1      -0.974   1.691   0.607  1.00  0.00           N  
HETATM    5  C3  UNL     1      -1.253   0.433  -0.060  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.248  -0.326   0.781  1.00  0.00           C  
HETATM    7  O2  UNL     1      -3.535   0.054   0.365  1.00  0.00           O  
HETATM    8  C5  UNL     1      -2.152  -1.804   0.650  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.751  -2.314   0.431  1.00  0.00           C  
HETATM   10  O3  UNL     1       0.030  -2.160   1.590  1.00  0.00           O  
HETATM   11  C7  UNL     1      -0.839  -3.757   0.135  1.00  0.00           C  
HETATM   12  O4  UNL     1      -1.492  -4.128  -0.862  1.00  0.00           O  
HETATM   13  O5  UNL     1      -0.225  -4.709   0.921  1.00  0.00           O  
HETATM   14  O6  UNL     1      -0.082  -1.613  -0.579  1.00  0.00           O  
HETATM   15  C8  UNL     1       0.055  -0.320  -0.144  1.00  0.00           C  
HETATM   16  C9  UNL     1       1.073   0.482  -0.913  1.00  0.00           C  
HETATM   17  O7  UNL     1       0.764   0.577  -2.267  1.00  0.00           O  
HETATM   18  C10 UNL     1       2.480  -0.054  -0.704  1.00  0.00           C  
HETATM   19  O8  UNL     1       2.757  -0.137   0.659  1.00  0.00           O  
HETATM   20  C11 UNL     1       3.430   0.993  -1.274  1.00  0.00           C  
HETATM   21  O9  UNL     1       4.752   0.611  -1.066  1.00  0.00           O  
HETATM   22  H1  UNL     1      -1.891   4.897   0.346  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.001   4.105   1.707  1.00  0.00           H  
HETATM   24  H3  UNL     1      -0.069   4.704   0.247  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.550   1.744   1.558  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.696   0.618  -1.046  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.166  -0.001   1.843  1.00  0.00           H  
HETATM   28  H7  UNL     1      -3.611  -0.115  -0.606  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.508  -2.256   1.609  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.801  -2.217  -0.143  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.491  -2.192   2.409  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.770  -5.413   1.424  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.443  -0.372   0.913  1.00  0.00           H  
HETATM   34  H13 UNL     1       1.066   1.519  -0.516  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.716  -0.287  -2.721  1.00  0.00           H  
HETATM   36  H15 UNL     1       2.618  -1.033  -1.175  1.00  0.00           H  
HETATM   37  H16 UNL     1       3.735  -0.012   0.789  1.00  0.00           H  
HETATM   38  H17 UNL     1       3.226   1.939  -0.704  1.00  0.00           H  
HETATM   39  H18 UNL     1       3.183   1.116  -2.337  1.00  0.00           H  
HETATM   40  H19 UNL     1       4.861  -0.367  -1.257  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5   25
CONECT    5    6   15   26
CONECT    6    7    8   27
CONECT    7   28
CONECT    8    9   29   30
CONECT    9   10   11   14
CONECT   10   31
CONECT   11   12   12   13
CONECT   13   32
CONECT   14   15
CONECT   15   16   33
CONECT   16   17   18   34
CONECT   17   35
CONECT   18   19   20   36
CONECT   19   37
CONECT   20   21   38   39
CONECT   21   40
END

HMDB0000230
     RDKit          3D
N-Acetylneuraminic acid
 40 40  0  0  0  0  0  0  0  0999 V2000
   -1.0141    4.2332    0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    2.9295   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935    2.9435   -1.1885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9739    1.6907    0.6069 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2534    0.4325   -0.0597 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2482   -0.3255    0.7808 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5349    0.0538    0.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1523   -1.8044    0.6501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7513   -2.3136    0.4313 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0298   -2.1603    1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8385   -3.7574    0.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4915   -4.1284   -0.8619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2248   -4.7091    0.9209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815   -1.6126   -0.5793 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0549   -0.3202   -0.1435 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0730    0.4816   -0.9127 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7635    0.5770   -2.2669 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4795   -0.0537   -0.7042 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7570   -0.1366    0.6588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4297    0.9931   -1.2736 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7516    0.6110   -1.0656 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8911    4.8974    0.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0007    4.1050    1.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0687    4.7041    0.2466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5502    1.7439    1.5577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6964    0.6178   -1.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -0.0009    1.8433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6110   -0.1146   -0.6058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5075   -2.2560    1.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -2.2165   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4906   -2.1925    2.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7703   -5.4132    1.4243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429   -0.3723    0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0660    1.5185   -0.5165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7158   -0.2874   -2.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6177   -1.0332   -1.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347   -0.0119    0.7893 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2257    1.9388   -0.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1826    1.1162   -2.3365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8606   -0.3671   -1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  2  0
 11 13  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 15  5  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  6
  6 27  1  1
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 13 32  1  0
 15 33  1  1
 16 34  1  1
 17 35  1  0
 18 36  1  6
 19 37  1  0
 20 38  1  0
 20 39  1  0
 21 40  1  0
M  END

Synonyms

Value	Source
5-N-ACETYL-BETA-D-neuraminIC ACID	ChEBI
beta-Neu5ac	ChEBI
5-N-ACETYL-b-D-neuraminate	Generator
5-N-ACETYL-b-D-neuraminic acid	Generator
5-N-ACETYL-beta-D-neuraminate	Generator
5-N-ACETYL-β-D-neuraminate	Generator
5-N-ACETYL-β-D-neuraminic acid	Generator
b-Neu5ac	Generator
Β-neu5ac	Generator
N-Acetylneuraminate	Generator
5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-D-glycero-b-D-galacto-2-nonulopyranosonic acid	HMDB
5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-D-glycero-D-galacto-2-nonulosonic acid	HMDB
5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-delta-glycero-beta-delta-galacto-2-nonulopyranosonic acid	HMDB
5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonate	HMDB
5-(Acetylamino)-3,5-dideoxy-delta-glycero-delta-galacto-2-nonulosonic acid	HMDB
5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonate	HMDB
5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid	HMDB
5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonate	HMDB
5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulosonic acid	HMDB
5-N-Acetyl-beta-delta-neuraminic acid	HMDB
5-N-Acetyl-D-neuraminate	HMDB
5-N-Acetyl-D-neuraminic acid	HMDB
5-N-Acetyl-delta-neuraminate	HMDB
5-N-Acetyl-delta-neuraminic acid	HMDB
5-N-Acetylneuraminate	HMDB
5-N-Acetylneuraminic acid	HMDB
Aceneuramate	HMDB
Aceneuramic acid	HMDB
Acetylneuraminate	HMDB
Acetylneuraminic acid	HMDB
b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonate	HMDB
b-5-Acetamido-3,5-dideoxy-D-glycero-D-galacto-nonulopyranosonic acid	HMDB
b-Sialic acid	HMDB
beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonate	HMDB
beta-5-Acetamido-3,5-dideoxy-delta-glycero-delta-galacto-nonulopyranosonic acid	HMDB
beta-Sialic acid	HMDB
Lactaminate	HMDB
Lactaminic acid	HMDB
N-Acetyl-b-D-neuraminate	HMDB
N-Acetyl-b-D-neuraminic acid	HMDB
N-Acetyl-b-neuraminate	HMDB
N-Acetyl-beta-delta-neuraminate	HMDB
N-Acetyl-beta-delta-neuraminic acid	HMDB
N-Acetyl-beta-neuraminate	HMDB
N-Acetyl-D-neuraminate	HMDB
N-Acetyl-D-neuraminic acid	HMDB
N-Acetyl-delta-neuraminate	HMDB
N-Acetyl-delta-neuraminic acid	HMDB
N-Acetyl-neuraminate	HMDB
N-Acetyl-neuraminic acid	HMDB
N-Acetylneuramate	HMDB
N-Acetylneuramic acid	HMDB
N-Acetylsialate	HMDB
N-Acetylsialic acid	HMDB
NAN	HMDB
NANA	HMDB
Neu5ac	HMDB
Sialic acid	HMDB
Acid, sialic	HMDB
Acid, N-acetylneuraminic	HMDB
N Acetylneuraminic acid	HMDB
N-Acetyl-beta-D-neuraminic acid	HMDB
N-Acetyl-beta-neuraminic acid	HMDB
N-Acetyl-β-D-neuraminic acid	HMDB
N-Acetyl-β-neuraminic acid	HMDB
N-Acetylneuraminic acid	HMDB

Molecular Formula

C₁₁H₁₉NO₉

Average Mass

309.2699

Monoisotopic Mass

309.105981211

IUPAC Name

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

Traditional Name

β-neu5ac

CAS Registry Number

19342-33-7

SMILES

[H][C@]1(O[C@@](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-PFQGKNLYSA-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 acid (CHEBI:45744 )

Functional Ontology

Not Available

Physical Properties

State

Expected 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)	-1.3	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	27.82 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
GC-MS	GC-MS Spectrum - GC-MS (7 TMS)	splash10-0fr2-1961000000-3acdbc4b39a5bf685996	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-014j-0492000000-8e4279660c77b0c70a30	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 7 TMS)	splash10-00l6-1792200000-863a168c10243229e892	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0fr2-1961000000-3acdbc4b39a5bf685996	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014j-0492000000-8e4279660c77b0c70a30	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00l6-1792200000-863a168c10243229e892	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0h2f-9660000000-f7a1f63f319c23f8e72a	2017-08-28	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-0zfr-4620249000-1d39f85a16504ef9ea46	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00di-0190000000-a3a5aaa2e10a6cfed08a	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0fk9-3900000000-7100e174e13e94736ae7	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00si-9300000000-1166885a787fd53086b0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100000000-260b6f27d6f3469ede2f	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9000000000-35b6da9206192d33828e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9301000000-47798651a02647e16452	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-000i-9000000000-1096dd07227387a97604	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-1091000000-11c42df33f8993522db0	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kc-5090000000-5d0c74aa0d8a2c8d321c	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-9320000000-cfda0db8085e62f50516	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4j-3391000000-68ee32ef5e2ba6223c42	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9110000000-9ae00577454ddf4db073	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9300000000-798cb916675bb1245a78	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03kc-0095000000-8f7746cc3f652b12033f	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02tc-1392000000-3e251c9d2583e71f866a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-7910000000-ba41b78e53cb934a9b19	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-3039000000-4348eff0515b0da3bc08	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-6290000000-5ac6f13cca0827ab0dd0	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-9100000000-ac22477eeca403481eff	2021-09-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)		2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Lysosome
Membrane
Nucleus

Biospecimen Locations

Adrenal Gland
Blood
Brain
Breast Milk
Cerebrospinal Fluid (CSF)
Feces
Neuron
Placenta
Prostate
Saliva
Testis
Urine

Tissue Locations

Adrenal Gland
Brain
Neuron
Placenta
Prostate
Testis

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191987	Sialidase-2	Enzyme	Q9Y3R4	Homo sapiens
MMDBp0191991	Sialidase-4	Enzyme	Q8WWR8	Homo sapiens
MMDBp0191992	Sialidase-1	Enzyme	Q99519	Homo sapiens
MMDBp0192001	Bifunctional UDP-N-acetylglucosamine 2-epimerase/N-acetylmannosamine kinase	Enzyme	Q9Y223	Homo sapiens
MMDBp0192002	Sialic acid synthase	Enzyme	Q9NR45	Homo sapiens
MMDBp0192066	N-acylneuraminate cytidylyltransferase	Enzyme	Q8NFW8	Homo sapiens
MMDBp0192183	Sialate O-acetylesterase	Enzyme	Q9HAT2	Homo sapiens
MMDBp0194149	N-acylneuraminate-9-phosphatase	Unknown	Q8TBE9	Homo sapiens
MMDBp0194150	N-acetylneuraminate lyase	Enzyme	Q9BXD5	Homo sapiens
MMDBp0196038	NEU1 protein	Enzyme	Q5JQI0	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000187	N-Acetylneuraminic acid	N-Acetylneuraminic acid	Solute carrier family 17 (acidic sugar transporter), member 5	N-Acetylneuraminate Transport into Lysososme	VMH	10581036 2768261
MMDBr0000188	N-Acetylneuraminic acid 9-phosphate	N-Acetylneuraminic acid	Acid phosphatase 5, tartrate resistant	N-Acetylneuraminate 9-Phosphate Phosphohydrolase	VMH	30371894
MMDBr0000189	N-Acetylneuraminic acid	N-Acetylneuraminic acid	Not Available	N-Acetylneuraminate Nuclear Import	VMH	30371894
MMDBr0000192	N-Acetylneuraminic acid	N-Acetylmannosamine	Not Available	N-Acetylneuraminate Lyase (Reversible)	VMH	30371894
MMDBr0000506	N-Acetylneuraminic acid	Cytidine 5'-monophosphate-N-acetylneuraminic acid	Not Available	CMP Sialic Acid Synthase	VMH	9689047
MMDBr0000507	N-Acetylneuraminic acid	Cytidine 5'-monophosphate-N-acetylneuraminic acid	Cytidine monophosphate n-acetylneuraminic acid synthetase	CMP Sialic Acid Synthase, Nuclear	VMH	9689047
MMDBr0002539	N-Acetylneuraminic acid	Hydrogen Ion	Not Available	N-Acetylneuraminate, Ferrocytochrome-B5:Oxygen Oxidoreductase (N-Acetyl-Hydroxylating)	VMH	11522391 12192086
MMDBr0006758	N-Acetylneuraminic acid	N-Acetylneuraminic acid	Not Available	N-Acetylneuraminate Proton Symport	VMH	30371894
MMDBr0006787	N-Acetylneuraminic acid	N-Acetylneuraminic acid	Not Available	N-Acetylneuraminate Export	VMH	30371894
MMDBr0006894	N-Acetylneuraminic acid	N-Acetylmannosamine	Not Available	N-Acetylneuraminate lyase	VMH	30371894
MMDBr0008059	N-Acetylneuraminic acid	N-Acetylneuraminic acid	Not Available	N-acetylneuraminic acid uptake via ABC transporter	VMH	30371894
MMDBr0008119	N-Acetylmannosamine	N-Acetylneuraminic acid	Not Available	N-acetylneuraminate synthase	VMH	30371894
MMDBr0008468	N-Acetylneuraminic acid	N-Acetylneuraminic acid	Not Available	N-acetylneuraminate proton symport, reversible	VMH	30371894
MMDBr0010691	Water	Acetic acid	Sialic acid acetylesterase	N-Acyl-O-Acetylneuraminate O-Acetylesterase	VMH	30371894
MMDBr0010838	N-Acetylneuraminic acid	Water	Not Available	N-Acetylneuraminate, Ferrocytochrome-B5:Oxygen Oxidoreductase (N-Acetyl-Hydroxylating)	VMH	30371894
MMDBr0012691	N-Acetylneuraminic acid	N-Acetylneuraminic acid	Not Available	N-acetylneuraminate sodium symport	VMH	30371894
MMDBr0019204	N-Acetylneuraminic acid	Pyruvic acid	N-acetylneuraminate lyase	Non-hydrolytic bond cleavage (or its reversal)	PathBank	31602464
MMDBr0024719	Water	Hydrogen Ion	Hemagglutinin-esterase	Hydrolysis of an ester group	RHEA	34755880
MMDBr0024795	Water	Hydrogen Ion	Hemagglutinin-esterase	Hydrolysis of an ester group	RHEA	34755880
MMDBr0024842	Hydrogen Ion	Hydrogen Ion	Sialic acid transporter NanT	Transport	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Salla disease	Increased	Association	Human Urine	HMDB	11992753

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	157	Human feces; Human stool; Human saliva; Human appendix biopsy; Human ; Human supragingival plaque; Human subgingival plaque; Human urine	Microbial culture; Metabolic reconstruction
Bacteria	Firmicutes	317	Human feces; Goat feces; Sheep feces; Human ; Human stool; Human urine; Human pleural fluid plaque; Pig ; Cattle ; Human saliva; Human supragingival plaque; Human subgingival plaque; Human mucosa; Human sputum	Microbial culture; Indirect association between microbiota composition and metabolites measured in host biospecimen; Metabolic reconstruction
Bacteria	Fusobacteria	22	Human mucosa; Human supragingival plaque; Human ; Human urine; Human feces; Human saliva; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria	Proteobacteria	148	Human feces; Human sputum; Pig ; Human ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Metabolic reconstruction
Bacteria	Actinobacteria	91	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human mucosa; Human saliva; Human stool	Metabolic reconstruction
Bacteria	Verrucomicrobia	2	Human ; Human feces	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction

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
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	64.4		31.7	225.4	umol/mmol creatinine	Adult (>18 years old)	Both	Salla disease	HMDB	11992753
Human Urine	Detected and Quantified			48.621	60.502	umol/mmol creatinine	Adult (>18 years old)	Both	SIALIDOSIS, normosomatic type	HMDB	7398077
Human Breast milk	Detected and Quantified	32.3565576				uM	Adult (>18 years old)	Female	Normal	HMDB	11787731
Human Blood	Detected and Quantified	2.0		1.0	3.0	uM	Adult (>18 years old)	Not Specified	Normal	HMDB	16624269
Human Urine	Detected and Quantified	5.4		2.5	8.6	umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	24023812
Human Urine	Detected and Quantified			8.920	18.279	umol/mmol creatinine	Adult (>18 years old)		Normal	HMDB	7398077
Human Blood	Detected and Quantified	0.57	1.26			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Cerebrospinal fluid (csf)	Detected and Quantified	11.9	7.1			uM	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Urine	Detected and Quantified	8.6	1.58			umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	Geigy Scientific Tables, 8th Rev edition, pp. 130. Edited by C. Lentner, West Cadwell, N.J.: Medical education Div., Ciba-Geigy Corp. Basel, Switzerland c1981-1992.
Human Saliva	Detected and Quantified	12.5	10.8			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	15.9	11.2			uM	Adult (>18 years old)	Female	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	17.1	12.1			uM	Adult (>18 years old)	Both	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Saliva	Detected and Quantified	41.1	34.6			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Adrenal gland	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Brain	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Neuron	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Prostate	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Testis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Male	Normal	HMDB	22308371
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	21761941
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0000230

DrugBank ID

DB04265

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

392810

KEGG Compound ID

C19910

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

N-Acetylneuraminic acid

METLIN ID

Not Available

PubChem Compound

445063

PDB ID

Not Available

ChEBI ID

45744

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Domschke W, Lux G, Domschke S: Furan H2-antagonist ranitidine inhibits pentagastrin-stimulated gastric secretion stronger than cimetidine. Gastroenterology. 1980 Dec;79(6):1267-71. [PubMed:6108279 ]
Bosmann HB: Platelet adhesiveness and aggregation. II. Surface sialic acid, glycoprotein: N-acetylneuraminic acid transferase, and neuraminidase of human blood platelets. Biochim Biophys Acta. 1972 Oct 25;279(3):456-74. [PubMed:5082512 ]
Rack J, Sonnenberg A: The influence of smoking and intravenous nicotine on gastric mucus. Hepatogastroenterology. 1983 Dec;30(6):258-60. [PubMed:6676147 ]
Bell JD, Brown JC, Nicholson JK, Sadler PJ: Assignment of resonances for 'acute-phase' glycoproteins in high resolution proton NMR spectra of human blood plasma. FEBS Lett. 1987 May 11;215(2):311-5. doi: 10.1016/0014-5793(87)80168-0. [PubMed:2438159 ]
Brusque A, Rotta L, Pettenuzzo LF, Junqueira D, Schwarzbold CV, Wyse AT, Wannmacher CM, Dutra-Filho CS, Wajner M: Chronic postnatal administration of methylmalonic acid provokes a decrease of myelin content and ganglioside N-acetylneuraminic acid concentration in cerebrum of young rats. Braz J Med Biol Res. 2001 Feb;34(2):227-31. doi: 10.1590/s0100-879x2001000200010. [PubMed:11175498 ]
Seppala R, Renlund M, Bernardini I, Tietze F, Gahl WA: Renal handling of free sialic acid in normal humans and patients with Salla disease or renal disease. Lab Invest. 1990 Aug;63(2):197-203. [PubMed:2381164 ]
Loomis RE, Prakobphol A, Levine MJ, Reddy MS, Jones PC: Biochemical and biophysical comparison of two mucins from human submandibular-sublingual saliva. Arch Biochem Biophys. 1987 Nov 1;258(2):452-64. doi: 10.1016/0003-9861(87)90366-3. [PubMed:3674885 ]
Nakata D, Munster AK, Gerardy-Schahn R, Aoki N, Matsuda T, Kitajima K: Molecular cloning of a unique CMP-sialic acid synthetase that effectively utilizes both deaminoneuraminic acid (KDN) and N-acetylneuraminic acid (Neu5Ac) as substrates. Glycobiology. 2001 Aug;11(8):685-92. doi: 10.1093/glycob/11.8.685. [PubMed:11479279 ]
Suzuki M, Suzuki A, Yamakawa T, Matsunaga E: Characterization of 2,7-anhydro-N-acetylneuraminic acid in human wet cerumen. J Biochem. 1985 Feb;97(2):509-15. doi: 10.1093/oxfordjournals.jbchem.a135085. [PubMed:4008466 ]
Baumkotter J, Cantz M, Mendla K, Baumann W, Friebolin H, Gehler J, Spranger J: N-Acetylneuraminic acid storage disease. Hum Genet. 1985;71(2):155-9. doi: 10.1007/BF00283373. [PubMed:4043964 ]
Weiss P, Tietze F, Gahl WA, Seppala R, Ashwell G: Identification of the metabolic defect in sialuria. J Biol Chem. 1989 Oct 25;264(30):17635-6. [PubMed:2808337 ]
McGee DJ, Rest RF: Regulation of gonococcal sialyltransferase, lipooligosaccharide, and serum resistance by glucose, pyruvate, and lactate. Infect Immun. 1996 Nov;64(11):4630-7. doi: 10.1128/iai.64.11.4630-4637.1996. [PubMed:8890217 ]
Sonnenberg A, Steinkamp U, Weise A, Berges W, Wienbeck M, Rohner HG, Peter P: Salivary secretion in reflux esophagitis. Gastroenterology. 1982 Oct;83(4):889-95. [PubMed:7106518 ]
Riebe D, Thorn W: Influence of carbohydrate moieties of human serum transferrin on the determination of its molecular mass by polyacrylamide gradient gel electrophoresis and staining with periodic acid-Schiff reagent. Electrophoresis. 1991 Apr;12(4):287-93. doi: 10.1002/elps.1150120410. [PubMed:2070783 ]
Watzlawick H, Walsh MT, Ehrhard I, Slayter HS, Haupt H, Schwick HG, Jourdian GW, Hase S, Schmid K, Brossmer R: The effect of the carbohydrate moiety upon the size and conformation of human plasma galactoglycoprotein as judged by electron microscopy and circular dichroism. Structural studies of a glycoprotein after stepwise enzymic carbohydrate removal. Biochem J. 1991 Aug 1;277 ( Pt 3):753-8. doi: 10.1042/bj2770753. [PubMed:1872812 ]
Gopaul KP, Crook MA: Sialic acid: a novel marker of cardiovascular disease? Clin Biochem. 2006 Jul;39(7):667-81. doi: 10.1016/j.clinbiochem.2006.02.010. Epub 2006 Apr 19. [PubMed:16624269 ]
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Dall'Olio F: The sialyl-alpha2,6-lactosaminyl-structure: biosynthesis and functional role. Glycoconj J. 2000 Oct;17(10):669-76. doi: 10.1023/a:1011077000164. [PubMed:11425186 ]
Keppler OT, Horstkorte R, Pawlita M, Schmidt C, Reutter W: Biochemical engineering of the N-acyl side chain of sialic acid: biological implications. Glycobiology. 2001 Feb;11(2):11R-18R. doi: 10.1093/glycob/11.2.11r. [PubMed:11287396 ]
Tettamanti G, Bassi R, Viani P, Riboni L: Salvage pathways in glycosphingolipid metabolism. Biochimie. 2003 Mar-Apr;85(3-4):423-37. doi: 10.1016/s0300-9084(03)00047-6. [PubMed:12770781 ]
Yamada K: [Chemo-pharmaceutical studies on the glycosphingolipid constituents from echinoderm, sea cucumbers, as the medicinal materials]. Yakugaku Zasshi. 2002 Dec;122(12):1133-43. doi: 10.1248/yakushi.122.1133. [PubMed:12510390 ]
Vimr ER, Kalivoda KA, Deszo EL, Steenbergen SM: Diversity of microbial sialic acid metabolism. Microbiol Mol Biol Rev. 2004 Mar;68(1):132-53. doi: 10.1128/MMBR.68.1.132-153.2004. [PubMed:15007099 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for N-Acetylneuraminic acid (MMDBc0000078)

MOL for #<Metabolite:0x000055d24aeece20>

3D MOL for #<Metabolite:0x000055d24aeece20>

3D SDF for #<Metabolite:0x000055d24aeece20>

3D-SDF for #<Metabolite:0x000055d24aeece20>

PDB for #<Metabolite:0x000055d24aeece20>

3D PDB for #<Metabolite:0x000055d24aeece20>

SMILES for #<Metabolite:0x000055d24aeece20>

INCHI for #<Metabolite:0x000055d24aeece20>

Structure for #<Metabolite:0x000055d24aeece20>

3D Structure for #<Metabolite:0x000055d24aeece20>