Milk Composition Database: Showing metabocard for N-Acetylneuraminic acid (BMDB0000230)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:07 UTC

Update Date

2020-06-04 20:56:29 UTC

MCDB ID

BMDB0000230

Secondary Accession Numbers

BMDB00230

Metabolite Identification

Common Name

N-Acetylneuraminic acid

Description

N-Acetylneuraminic acid, also known as N-acetylneuraminate or sialic acid, belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. N-Acetylneuraminic acid exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. N-Acetylneuraminic acid exists in all living organisms, ranging from bacteria to humans. N-Acetylneuraminic acid participates in a number of enzymatic reactions, within cattle. In particular, N-Acetylneuraminic acid can be biosynthesized from N-acetylmannosamine and phosphoenolpyruvic acid; which is catalyzed by the enzyme sialic acid synthase. In addition, N-Acetylneuraminic acid can be converted into N-acetylmannosamine and pyruvic acid; which is mediated by the enzyme N-acetylneuraminate lyase. In cattle, N-acetylneuraminic acid is involved in the metabolic pathway called the amino sugar metabolism pathway. N-Acetylneuraminic acid is a potentially toxic compound. N-Acetylneuraminic acid has been found to be associated with several diseases known as sialidosis, normosomatic type, irritable bowel syndrome, ulcerative colitis, and colorectal cancer; also n-acetylneuraminic acid has been linked to the inborn metabolic disorders including salla disease.

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

Chemical Formula

C₁₁H₁₉NO₉

Average Molecular Weight

309.2699

Monoisotopic Molecular Weight

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

131-48-6

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 )

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
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	1	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)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	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)	Not Available	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value	Reference	Details
Detected and Quantified	32 - 42 uM	International Dai...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details
Detected and Quantified	462 uM	The N-acetyl neur...	details
Detected but not Quantified	Not Applicable	Kurt J. Boudonck,...	details

External Links

HMDB ID

HMDB0000230

DrugBank ID

DB04265

Phenol Explorer Compound ID

Not Available

FoodDB 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

References

Synthesis Reference

Yamamoto, Toshihiro; Teshima, Tadashi; Inami, Kaoru; Shiba, Tetsuo. Synthesis of sialic acid through aldol condensation of glucose with oxalacetic acid. Tetrahedron Letters (1992), 33(3), 325-8.

Material Safety Data Sheet (MSDS)

Not Available

General References

Paul McJarrow, Janneke van Amelsfort-Schoonbeek (2004). International Dairy Journal: Volume 14, Issue 7, July 2004, Pages 571-579. International Dairy Journal.
Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
P. A. Morrissey (1973). The N-acetyl neuraminic-acid content of the milk of various species Journal of Dairy Research (1973), 40: 421-425 Cambridge University Press doi: 10.1017/S0022029900014795 (About doi) . Journal of Dairy Research.

Showing metabocard for N-Acetylneuraminic acid (BMDB0000230)

Structure for BMDB0000230 (N-Acetylneuraminic acid)