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Human Metabolome Database Version 2.5

 

Showing metabocard for N-Acetylneuraminate 9-phosphate (HMDB06268)

Legend: metabolite field enzyme field

Version 2.5
Creation Date 2007-05-22 21:33:23
Update Date 2009-05-05 21:00:45
Accession Number HMDB06268
Secondary Accession Numbers Not Available
Common Name N-Acetylneuraminate 9-phosphate
Description N-Acetylneuraminate 9-phosphate is an intermediate in Aminosugars metabolism. N-Acetylneuraminate 9-phosphate is the 4th to last step in the synthesis of colominate and is converted from N-Acetyl-D-mannosamine-6-phosphate via the enzyme N-Acylneuraminate-9-phosphate synthase (EC 2.5.1.57). It is then converted to N-Acetylneuraminate via the enzyme N-acylneuraminate-9-phosphatase(EC 3.1.3.29).
Synonyms Not Available
Chemical IUPAC Name (4S,5R,6R)-5-acetamido-6-[(1R,2R)-1,2-dihydroxy-3-phosphonooxypropyl]-2,
Chemical Formula C11H20NO12P
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Sugar Phosphates
Sub Class
  • Disaccharide phosphates
Family
  • Mammalian Metabolite
Species
  • hemiacetal
  • secondary alcohol
  • 1,2-diol
  • carboxylic acid
  • secondary carboxylic acid amide
  • phosphoric acid ester
  • heterocyclic compound
Biofunction
—
Application
—
Source
  • Endogenous
Average Molecular Weight 389.250
Monoisotopic Molecular Weight 389.072327
Isomeric SMILES CC(=O)N[C@H]1[C@H](O)CC(O)(O[C@@H]1[C@H](O)[C@H](O)COP(O)(O)=O)C(O)=O
Canonical SMILES CC(=O)NC1C(O)CC(O)(OC1C(O)C(O)COP(O)(O)=O)C(O)=O
KEGG Compound ID C06241 Link Image
BioCyc ID Not Available
BiGG ID 47736 Link Image
Wikipedia Link Not Available
NuGOwiki Link HMDB06268 Link Image
Metagene Link HMDB06268 Link Image
METLIN ID Not Available
PubChem Compound 440962 Link Image
PubChem Substance Not Available
ChEBI ID Not Available
CAS Registry Number Not Available
InChI Identifier InChI=1/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+,11u/m1/s1
Synthesis Reference Not Available
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 15.900001 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -3
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -2.57 [Predicted by ALOGPS] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location Not Available
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Associated Disorders Not Available
OMIM ID Not Available
Pathways
Name SMPDB Link KEGG Link
Amino Sugar Metabolism SMP00045 Link Image map00520 Link Image
General References Not Available
Metabolic Enzymes
  1. Sialic acid synthase
  2. N-acylneuraminate-9-phosphatase
  3. cDNA, FLJ96858, Homo sapiens N-acetylneuraminic acid synthase (sialic acid synthase) (NANS), mRNA (N-acetylneuraminic acid synthase (Sialic acid synthase), isoform CRA_b)
  4. cDNA FLJ30910 fis, clone FEBRA2006270, highly similar to N-acylneuraminate-9-phosphatase (EC 3.1.3.29)
Enzyme 1 [top]
Enzyme 1 ID 5569
Enzyme 1 Name Sialic acid synthase
Enzyme 1 Synonyms
  1. N-acetylneuraminate synthase
  2. N- acetylneuraminic acid synthase
  3. N-acetylneuraminate-9-phosphate synthase
  4. N-acetylneuraminic acid phosphate synthase
Enzyme 1 Gene Name NANS
Enzyme 1 Protein Sequence >Sialic acid synthase 
MPLELELCPGRWVGGQHPCFIIAEIGQNHQGDLDVAKRMIRMAKECGADCAKFQKSELEF
KFNRKALERPYTSKHSWGKTYGEHKRHLEFSHDQYRELQRYAEEVGIFFTASGMDEMAVE
FLHELNVPFFKVGSGDTNNFPYLEKTAKKGRPMVISSGMQSMDTMKQVYQIVKPLNPNFC
FLQCTSAYPLQPEDVNLRVISEYQKLFPDIPIGYSGHETGIAISVAAVALGAKVLERHIT
LDKTWKGSDHSASLEPGELAELVRSVRLVERALGSPTKQLLPCEMACNEKLGKSVVAKVK
IPEGTILTMDMLTVKVGEPKGYPPEDIFNLVGKKVLVTVEEDDTIMEELVDNHGKKIKS
Enzyme 1 Number of Residues 359
Enzyme 1 Molecular Weight 40308
Enzyme 1 Theoretical pI 6.73
Enzyme 1 GO Classification Not Available
Enzyme 1 General Function Cell wall/membrane/envelope biogenesis
Enzyme 1 Specific Function Produces N-acetylneuraminic acid (Neu5Ac) and 2-keto-3- deoxy-D-glycero-D-galacto-nononic acid (KDN). Can also use N- acetylmannosamine 6-phosphate and mannose 6-phosphate as substrates to generate phosphorylated forms of Neu5Ac and KDN, respectively
Enzyme 1 Pathways
Enzyme 1 Reactions
  • phosphoenolpyruvate + N-acyl-D-mannosamine 6-phosphate + H2O = N-acylneuraminate 9-phosphate + phosphate
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 8453156 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q9NR45 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name SIAS_HUMAN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1080 bp 
ATGCCGCTGGAGCTGGAGCTGTGTCCCGGGCGCTGGGTGGGCGGGCAACACCCGTGCTTC
ATCATTGCCGAGATCGGCCAGAACCACCAGGGCGACCTGGACGTAGCCAAGCGCATGATC
CGCATGGCCAAGGAGTGTGGGGCTGATTGTGCCAAGTTCCAGAAGAGTGAGCTAGAATTC
AAGTTTAATCGGAAAGCCTTGGAGAGGCCATACACCTCGAAGCATTCCTGGGGGAAGACG
TACGGGGAGCACAAACGACATCTGGAGTTCAGCCATGACCAGTACAGGGAGCTGCAGAGG
TACGCCGAGGAGGTTGGGATCTTCTTCACTGCCTCTGGCATGGATGAGATGGCAGTTGAA
TTCCTGCATGAACTGAATGTTCCATTTTTCAAAGTTGGATCTGGAGACACTAATAATTTT
CCTTATCTGGAAAAGACAGCCAAAAAAGGTCGCCCAATGGTGATCTCCAGTGGGATGCAG
TCAATGGACACCATGAAGCAAGTTTATCAGATCGTGAAGCCCCTCAACCCCAACTTCTGC
TTCTTGCAGTGTACCAGCGCATACCCGCTCCAGCCTGAGGACGTCAACCTGCGGGTCATC
TCGGAATATCAGAAGCTCTTTCCTGACATTCCCATAGGGTATTCTGGGCATGAAACAGGC
ATAGCGATATCTGTGGCCGCAGTGGCTCTGGGGGCCAAGGTGTTGGAACGTCACATAACT
TTGGACAAGACCTGGAAGGGGAGTGACCACTCGGCCTCGCTGGAGCCTGGAGAACTGGCC
GAGCTGGTGCGGTCAGTGCGTCTTGTGGAGCGTGCCCTGGGCTCCCCAACCAAGCAGCTG
CTGCCCTGTGAGATGGCCTGCAATGAGAAGCTGGGCAAGTCTGTGGTGGCCAAAGTGAAA
ATTCCGGAAGGCACCATTCTAACAATGGACATGCTCACCGTGAAGGTGGGTGAGCCCAAA
GCCTATCCTCCTGAAGACATCTTTAATCTAGTGGGCAAGAAGGTCCTGGTCACTGTTGAA
GAGGATGACACCATCATGGAAGAATTGGTAGATAATCATGGCAAAAAAATCAAGTCTTAA
Enzyme 1 GenBank Gene ID AF257466 Link Image
Enzyme 1 GeneCard ID NANS Link Image
Enzyme 1 GenAtlas ID NANS Link Image
Enzyme 1 HGNC ID HGNC:19237 Link Image
Enzyme 1 Chromosome Location Not Available
Enzyme 1 Locus Not Available
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References
  1. Lawrence SM, Huddleston KA, Pitts LR, Nguyen N, Lee YC, Vann WF, Coleman TA, Betenbaugh MJ: Cloning and expression of the human N-acetylneuraminic acid phosphate synthase gene with 2-keto-3-deoxy-D-glycero- D-galacto-nononic acid biosynthetic ability. J Biol Chem. 2000 Jun 9;275(23):17869-77. [PubMed Link Image]
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 12983
Enzyme 2 Name N-acylneuraminate-9-phosphatase
Enzyme 2 Synonyms
  1. Neu5Ac-9-Pase
  2. Haloacid dehalogenase-like hydrolase domain-containing protein 4
Enzyme 2 Gene Name NANP
Enzyme 2 Protein Sequence >N-acylneuraminate-9-phosphatase 
MGLSRVRAVFFDLDNTLIDTAGASRRGMLEVIKLLQSKYHYKEEAEIICDKVQVKLSKEC
FHPYNTCITDLRTSHWEEAIQETKGGAANRKLAEECYFLWKSTRLQHMTLAEDVKAMLTE
LRKEVRLLLLTNGDRQTQREKIEACACQSYFDAVVVGGEQREEKPAPSIFYYCCNLLGVQ
PGDCVMVGDTLETDIQGGLNAGLKATVWINKNGIVPLKSSPVPHYMVSSVLELPALLQSI
DCKVSMST
Enzyme 2 Number of Residues 248
Enzyme 2 Molecular Weight 27813
Enzyme 2 Theoretical pI 6.35
Enzyme 2 GO Classification
Function
  • catalytic activity
  • hydrolase activity
  • hydrolase activity, acting on ester bonds
  • phosphoglycolate phosphatase activity
  • phosphoric ester hydrolase activity
  • phosphoric monoester hydrolase activity
Process
  • metabolism
  • physiological process
Component
—
Enzyme 2 General Function Not Available
Enzyme 2 Specific Function N-acylneuraminate 9-phosphate + H(2)O = N- acylneuraminate + phosphate
Enzyme 2 Pathways
Enzyme 2 Reactions
  • N-acylneuraminate 9-phosphate + H2O = N-acylneuraminate + phosphate [RN:R02597] ALL_REAC R02597 > R01805
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein Not Available
Enzyme 2 UniProtKB/Swiss-Prot ID Q8TBE9 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name NANP_HUMAN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence Not Available
Enzyme 2 GenBank Gene ID AL031673 Link Image
Enzyme 2 GeneCard ID Q8TBE9 Link Image
Enzyme 2 GenAtlas ID NANP Link Image
Enzyme 2 HGNC ID HGNC:16140 Link Image
Enzyme 2 Chromosome Location Not Available
Enzyme 2 Locus Not Available
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. Deloukas P, Matthews LH, Ashurst J, Burton J, Gilbert JG, Jones M, Stavrides G, Almeida JP, Babbage AK, Bagguley CL, Bailey J, Barlow KF, Bates KN, Beard LM, Beare DM, Beasley OP, Bird CP, Blakey SE, Bridgeman AM, Brown AJ, Buck D, Burrill W, Butler AP, Carder C, Carter NP, Chapman JC, Clamp M, Clark G, Clark LN, Clark SY, Clee CM, Clegg S, Cobley VE, Collier RE, Connor R, Corby NR, Coulson A, Coville GJ, Deadman R, Dhami P, Dunn M, Ellington AG, Frankland JA, Fraser A, French L, Garner P, Grafham DV, Griffiths C, Griffiths MN, Gwilliam R, Hall RE, Hammond S, Harley JL, Heath PD, Ho S, Holden JL, Howden PJ, Huckle E, Hunt AR, Hunt SE, Jekosch K, Johnson CM, Johnson D, Kay MP, Kimberley AM, King A, Knights A, Laird GK, Lawlor S, Lehvaslaiho MH, Leversha M, Lloyd C, Lloyd DM, Lovell JD, Marsh VL, Martin SL, McConnachie LJ, McLay K, McMurray AA, Milne S, Mistry D, Moore MJ, Mullikin JC, Nickerson T, Oliver K, Parker A, Patel R, Pearce TA, Peck AI, Phillimore BJ, Prathalingam SR, Plumb RW, Ramsay H, Rice CM, Ross MT, Scott CE, Sehra HK, Shownkeen R, Sims S, Skuce CD, Smith ML, Soderlund C, Steward CA, Sulston JE, Swann M, Sycamore N, Taylor R, Tee L, Thomas DW, Thorpe A, Tracey A, Tromans AC, Vaudin M, Wall M, Wallis JM, Whitehead SL, Whittaker P, Willey DL, Williams L, Williams SA, Wilming L, Wray PW, Hubbard T, Durbin RM, Bentley DR, Beck S, Rogers J: The DNA sequence and comparative analysis of human chromosome 20. Nature. 2001 Dec 20-27;414(6866):865-71. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available
Enzyme 3 [top]
Enzyme 3 ID 16530
Enzyme 3 Name cDNA, FLJ96858, Homo sapiens N-acetylneuraminic acid synthase (sialic acid synthase) (NANS), mRNA (N-acetylneuraminic acid synthase (Sialic acid synthase), isoform CRA_b)
Enzyme 3 Synonyms Not Available
Enzyme 3 Gene Name NANS
Enzyme 3 Protein Sequence >cDNA, FLJ96858, Homo sapiens N-acetylneuraminic acid synthase (sialic acid synthase) (NANS), mRNA (N-acetylneuraminic acid synthase (Sialic acid synthase), isoform CRA_b) 
MPLELELCPGRWVGGQHPCFIIAEIGQNHQGDLDVAKRMIRMAKECGADCAKFQKSELEF
KFNRKALERPYTSKHSWGKTYGEHKRHLEFSHDQYRELQRYAEEVGIFFTASGMDEMAVE
FLHELNVPFFKVGSGDTNNFPYLEKTAKKGRPMVISSGMQSMDTMKQVYQIVKPLNPNFC
FLQCTSAYPLQPEDVNLRVISEYQKLFPDIPIGYSGHETGIAISVAAVALGAKVLERHIT
LDKTWKGSDHSASLEPGELAELVRSVRLVERALGSPTKQLLPCEMACNEKLGKSVVAKVK
IPEGTILTMDMLTVKVGEPKGYPPEDIFNLVGKKVLVTVEEDDTIMEELVDNHGKKIKS
Enzyme 3 Number of Residues 359
Enzyme 3 Molecular Weight 40308
Enzyme 3 Theoretical pI 6.73
Enzyme 3 GO Classification Not Available
Enzyme 3 General Function Cell wall/membrane/envelope biogenesis
Enzyme 3 Specific Function Not Available
Enzyme 3 Pathways Not Available
Enzyme 3 Reactions Not Available
Enzyme 3 Pfam Domain Function
Enzyme 3 Signals
  • None
Enzyme 3 Transmembrane Regions
  • None
Enzyme 3 Essentiality Not Available
Enzyme 3 GenBank ID Protein Not Available
Enzyme 3 UniProtKB/Swiss-Prot ID B2RE98 Link Image
Enzyme 3 UniProtKB/Swiss-Prot Entry Name B2RE98_HUMAN Link Image
Enzyme 3 PDB ID Not Available
Enzyme 3 Cellular Location Not Available
Enzyme 3 Gene Sequence Not Available
Enzyme 3 GenBank Gene ID AK316608 Link Image
Enzyme 3 GeneCard ID B2RE98 Link Image
Enzyme 3 GenAtlas ID Not Available
Enzyme 3 HGNC ID Not Available
Enzyme 3 Chromosome Location Not Available
Enzyme 3 Locus Not Available
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 General References Not Available
Enzyme 3 Metabolite References Not Available
Enzyme 4 [top]
Enzyme 4 ID 16531
Enzyme 4 Name cDNA FLJ30910 fis, clone FEBRA2006270, highly similar to N-acylneuraminate-9-phosphatase (EC 3.1.3.29)
Enzyme 4 Synonyms
  1. SubName: N-acetylneuraminic acid phosphatase
Enzyme 4 Gene Name NANP
Enzyme 4 Protein Sequence >cDNA FLJ30910 fis, clone FEBRA2006270, highly similar to N-acylneuraminate-9-phosphatase (EC 3.1.3.29) 
MGLSRVRAVFFDLDNTLIDTAGASRRGMLEVIKLLQSKYHYKEEAEIICDKVQVKLSKEC
FHPYNTCITDLRTSHWEEAIQETKGGAANRKLAEECYFLWKSTRLQHMTLAEDVKAMLTE
LRKEVRLLLLTNGDRQTQREKIEACACQSYFDAVVVGGEQREEKPAPSIFYYCCNLLGVQ
PGDCVMVGDTLETDIQGGLNAGLKATVWINKNGIVPLKSSPVPHYMVSSVLELPALLQSI
DCKVSMST
Enzyme 4 Number of Residues 248
Enzyme 4 Molecular Weight 27813
Enzyme 4 Theoretical pI 6.35
Enzyme 4 GO Classification
Function
  • catalytic activity
  • hydrolase activity
  • hydrolase activity, acting on ester bonds
  • phosphoglycolate phosphatase activity
  • phosphoric ester hydrolase activity
  • phosphoric monoester hydrolase activity
Process
  • metabolism
  • physiological process
Component
—
Enzyme 4 General Function Not Available
Enzyme 4 Specific Function Not Available
Enzyme 4 Pathways Not Available
Enzyme 4 Reactions
  • N-acylneuraminate 9-phosphate + H2O = N-acylneuraminate + phosphate [RN:R02597] ALL_REAC R02597 > R01805
Enzyme 4 Pfam Domain Function
Enzyme 4 Signals
  • None
Enzyme 4 Transmembrane Regions
  • None
Enzyme 4 Essentiality Not Available
Enzyme 4 GenBank ID Protein Not Available
Enzyme 4 UniProtKB/Swiss-Prot ID B3KP12 Link Image
Enzyme 4 UniProtKB/Swiss-Prot Entry Name B3KP12_HUMAN Link Image
Enzyme 4 PDB ID Not Available
Enzyme 4 Cellular Location Not Available
Enzyme 4 Gene Sequence Not Available
Enzyme 4 GenBank Gene ID AK055472 Link Image
Enzyme 4 GeneCard ID B3KP12 Link Image
Enzyme 4 GenAtlas ID Not Available
Enzyme 4 HGNC ID Not Available
Enzyme 4 Chromosome Location 20
Enzyme 4 Locus 20p11.1
Enzyme 4 SNPs SNPJam Report Link Image
Enzyme 4 General References Not Available
Enzyme 4 Metabolite References Not Available