Bovine Metabolome Database: Showing metabocard for N-Acetylneuraminic acid 9-phosphate (BMDB0004381)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 23:09:24 UTC

Update Date

2020-04-22 15:13:47 UTC

BMDB ID

BMDB0004381

Secondary Accession Numbers

BMDB04381

Metabolite Identification

Common Name

N-Acetylneuraminic acid 9-phosphate

Description

N-Acetylneuraminic acid 9-phosphate belongs to the class of organic compounds known as n-acylneuraminate-9-phosphates. These are neuraminic acids carrying an N-acyl substituent, as well as a phosphate group at the O9-position. N-Acetylneuraminic acid 9-phosphate exists in all living organisms, ranging from bacteria to humans. Based on a literature review a significant number of articles have been published on N-Acetylneuraminic acid 9-phosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-Acetylneuraminate 9-phosphate	ChEBI
N-Acetylneuraminic acid 9-phosphoric acid	Generator
5-(acetylamino)-3,5-Dideoxy-D-glycero-D-galacto-2-nonulosonic acid 9-(dihydrogen phosphate)	HMDB
N-Acetyl- 9-(dihydrogen phosphate)-neuraminic acid	HMDB
N-Acetyl-neuraminic acid-9-phosphate	HMDB

Chemical Formula

C₁₁H₂₀NO₁₂P

Average Molecular Weight

389.2498

Monoisotopic Molecular Weight

389.072311621

IUPAC Name

(4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

Traditional Name

(4S,5R,6R)-6-[(1R,2R)-1,2-dihydroxy-3-(phosphonooxy)propyl]-5-acetamido-2,4-dihydroxyoxane-2-carboxylic acid

CAS Registry Number

37992-17-9

SMILES

[H][C@]1(OC(O)(C[C@H](O)[C@H]1NC(C)=O)C(O)=O)[C@H](O)[C@H](O)COP(O)(O)=O

InChI Identifier

InChI=1S/C11H20NO12P/c1-4(13)12-7-5(14)2-11(19,10(17)18)24-9(7)8(16)6(15)3-23-25(20,21)22/h5-9,14-16,19H,2-3H2,1H3,(H,12,13)(H,17,18)(H2,20,21,22)/t5-,6+,7+,8+,9+,11?/m0/s1

InChI Key

SQMNIXJSBCSNCI-LUWBGTNYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as n-acylneuraminate-9-phosphates. These are neuraminic acids carrying an N-acyl substituent, as well as a phosphate group at the O9-position.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

N-acylneuraminate-9-phosphates

Alternative Parents

Substituents

N-acylneuraminate-9-phosphate
Neuraminic acid
C-glucuronide
C-glycosyl compound
Glycosyl compound
Monoalkyl phosphate
Alpha-hydroxy acid
Organic phosphoric acid derivative
Hydroxy acid
Oxane
Phosphoric acid ester
Alkyl phosphate
Pyran
Acetamide
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Hemiacetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organic oxide
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

amino sugar phosphate (CHEBI:27438 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-4.235	Not Available

Predicted Properties

Property	Value	Source
logP	-2.6	ALOGPS
logP	-3.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	223.31 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.65 m³·mol⁻¹	ChemAxon
Polarizability	32.62 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9865000000-ea42a1918e170bac9d1c	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-03di-3811119000-2bddb7ead2e38a7d54bc	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("N-Acetylneuraminic acid 9-phosphate,4TBDMS,#20" TMS) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-1139000000-31a61c834ec1e7590647	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dm-6798000000-0e71876811a2de198680	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ow-9370000000-8520f146007338380dde	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0umj-4494000000-651a0b7cbf5a8bf286f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-9000000000-abb61d928b00d92157c7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9e6e329e3f59fa84a900	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0079-4009000000-416f62d688ca6890bcbc	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9010000000-b9d33d49f34714b29ed1	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-91afd217638adb8dd69a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00dl-0069000000-a644d0e6cfb07a9db310	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0007-4197000000-f28ef28b4c9147a10830	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000x-9310000000-12f94537e5890a9069bf	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0004381

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023369

KNApSAcK ID

Not Available

Chemspider ID

389789

KEGG Compound ID

C06241

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440962

PDB ID

Not Available

ChEBI ID

27438

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for N-Acetylneuraminic acid 9-phosphate (BMDB0004381)

Structure for BMDB0004381 (N-Acetylneuraminic acid 9-phosphate)