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

2024-10-13 10:50:15 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 SDF PDB SMILES InChI

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

Not Available

Traditional Name

Not Available

CAS Registry Number

19342-33-7

SMILES

Not Available

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

Not Available

Spectra

Not Available

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000188	N-Acetylneuraminic acid 9-phosphate	N-Acetylneuraminic acid	acid phosphatase 5, tartrate resistant	VMH	30371894
MMDBr0000192	N-Acetylneuraminic acid	N-Acetylmannosamine	Not Available	VMH	30371894
MMDBr0000506	N-Acetylneuraminic acid	Cytidine 5'-monophosphate-N-acetylneuraminic acid	Not Available	VMH	9689047
MMDBr0000507	N-Acetylneuraminic acid	Cytidine 5'-monophosphate-N-acetylneuraminic acid	cytidine monophosphate N-acetylneuraminic acid synthetase	VMH; KEGG	9689047
MMDBr0002539	N-Acetylneuraminic acid	N-Glycolylneuraminic acid	Not Available	VMH	11522391 12192086
MMDBr0006894	N-Acetylneuraminic acid	N-Acetylmannosamine	Not Available	VMH; KEGG	30371894
MMDBr0008119	N-Acetylmannosamine	N-Acetylneuraminic acid	Not Available	VMH	30371894
MMDBr0010691	N-acetyl-O-acetylneuraminate	Acetic acid	sialic acid acetylesterase	VMH; KEGG	30371894
MMDBr0010838	N-Acetylneuraminic acid	N-Glycolylneuraminic acid	Not Available	VMH; KEGG	30371894

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	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

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 ]
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Showing metabocard for N-Acetylneuraminic acid (MMDBc0000078)

MOL for #<Metabolite:0x00007fdb19419000>

3D MOL for #<Metabolite:0x00007fdb19419000>

3D SDF for #<Metabolite:0x00007fdb19419000>

3D-SDF for #<Metabolite:0x00007fdb19419000>

PDB for #<Metabolite:0x00007fdb19419000>

3D PDB for #<Metabolite:0x00007fdb19419000>

SMILES for #<Metabolite:0x00007fdb19419000>

INCHI for #<Metabolite:0x00007fdb19419000>

Structure for #<Metabolite:0x00007fdb19419000>

3D Structure for #<Metabolite:0x00007fdb19419000>