NP-MRD: Showing NP-Card for N-Acetylneuraminic acid (NP0000585)

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Record Information

Version

1.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2020-11-24 22:16:40 UTC

NP-MRD ID

NP0000585

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-Acetylneuraminic acid

Description

N-acetylneuraminic acid (NeuAc) or 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: UDP-N-acetylglucosamine (UDP-GlcNAc) N-acetylmannosamine (ManNAc) ManNAc 6-phosphate NeuAc 9-phosphate NeuAc 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 of 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 gangliosides 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 linked to 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>
NP0000585

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

Synonyms

Value	Source
5-N-ACETYL-BETA-D-neuraminIC ACID	ChEBI
beta-Neu5ac	ChEBI
WURCS=2.0/1,1,0/[aad21122h-2b_2-6_5*ncc/3=o]/1/	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

Chemical Formula

C₁₁H₁₉NO₉

Average Mass

309.2699 Da

Monoisotopic Mass

309.10598 Da

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

131-48-6

SMILES

CC(=O)N[C@@H]1[C@@H](O)C[C@](O)(O[C@H]1[C@H](O)[C@H](O)CO)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-/m0/s1

InChI Key

SQVRNKJHWKZAKO-PFQGKNLYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Artemia salina	LOTUS Database	35616633
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Escherichia coli	KNApSAcK Database	22123792
Homo sapiens (Urine)	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	186 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

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

External Links

HMDB ID

HMDB0000230

DrugBank ID

DB04265

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00019584

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

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
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Showing NP-Card for N-Acetylneuraminic acid (NP0000585)

MOL for NP0000585 (N-Acetylneuraminic acid)

3D MOL for NP0000585 (N-Acetylneuraminic acid)

3D SDF for NP0000585 (N-Acetylneuraminic acid)

3D-SDF for NP0000585 (N-Acetylneuraminic acid)

PDB for NP0000585 (N-Acetylneuraminic acid)

3D PDB for NP0000585 (N-Acetylneuraminic acid)

SMILES for NP0000585 (N-Acetylneuraminic acid)

INCHI for NP0000585 (N-Acetylneuraminic acid)

Structure for NP0000585 (N-Acetylneuraminic acid)

3D Structure for NP0000585 (N-Acetylneuraminic acid)