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Showing metabocard for Acetylphosphate (HMDB0001494)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
enzymes (2) Show 2 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-07 16:45:30 UTC
HMDB IDHMDB0001494
Secondary Accession Numbers
  • HMDB01494
Metabolite Identification
Common NameAcetylphosphate
DescriptionAcetylphosphate, also known as acetyl-p, belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure R-CO-P(O)(O)OH, R=H or organyl. Since acetylphosphate synthesis is known to depend on cholinesterase activity, pseudocholinesterase was assumed to participate to a small extent in acetylphosphate synthesis by cancerous serum. It is also an intermediate in pyruvate metabolism. Acetylphosphate is a drug. Acetylphosphate exists in all living organisms, ranging from bacteria to humans. Acetylphosphate can be converted into acetic acid; which is mediated by the enzyme acylphosphatase-1. It is generated from pyruvate and the formation is catalyzed by pyruvate oxidase (EC:1.2.3.3). In humans, acetylphosphate is involved in the metabolic disorder called the pyruvate dehydrogenase complex deficiency pathway. It is generated from sulfoacetaldehyde, converted to acetyl-CoA and acetate via phosphate acetyltransferase (EC:2.3.1.8) and acetate kinase (EC:2.7.2.1) respectively. Acetylphosphate or actyl phosphate is a compound involved in taurine and hypotaurine metabolism as well as pyruvate metabolism. Cancerous serum produced 37% less acetylphosphate than normal serum.
Structure
Data?1582752205
MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001494 (Acetylphosphate)


  Mrv1652305271900012D          

  8  7  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0001494 (Acetylphosphate)

Download
3D SDF for HMDB0001494 (Acetylphosphate)

  Mrv1652305271900012D          

  8  7  0  0  0  0            999 V2000
    0.1105   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6039   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001494

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)

> <INCHI_KEY>
LIPOUNRJVLNBCD-UHFFFAOYSA-N

> <FORMULA>
C2H5O5P

> <MOLECULAR_WEIGHT>
140.0319

> <EXACT_MASS>
139.987459782

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
9.874052763828468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(acetyloxy)phosphonic acid

> <ALOGPS_LOGP>
-0.92

> <JCHEM_LOGP>
-0.8772108599999999

> <ALOGPS_LOGS>
-0.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.276046285834895

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.2407072572323323

> <JCHEM_PKA_STRONGEST_BASIC>
-7.387612001654629

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
23.8034

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
acetylphosphate

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for HMDB0001494 (Acetylphosphate)
https://cactus.nci.nih.gov/chemical/structure/CC(=O)OP(O)(O)=O/file?format=sd...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:12})
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.9768   -0.7107   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6193   -0.0645   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5293    1.1294    0.1606 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5101   -0.8153   -0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9016   -0.0506    0.0302 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0801    0.9464   -1.2213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974   -1.1287    0.0324 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9360    0.7269    1.2891 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3162   -1.0041    0.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9116   -1.5929   -0.7421 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6843   -0.0026   -0.5365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0673    0.5042   -2.0812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9792   -0.7379    0.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  1 10  1  0  0  0  0
  1 11  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  2  0  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
M  END
$$$$

Download
PDB for HMDB0001494 (Acetylphosphate)
HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.206  -3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.127  -1.540   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0       1.540   0.000   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0       1.540   1.540   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.080   0.000   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

Download
3D PDB for HMDB0001494 (Acetylphosphate)
COMPND    https://cactus.nci.nih.gov/chemical/structure/CC(=O)OP(O)(O)=O/file?format=sd... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1       2.977  -0.711  -0.105  1.00  0.00           C  
HETATM    2  C   UNL     1       1.619  -0.065  -0.002  1.00  0.00           C  
HETATM    3  O   UNL     1       1.529   1.129   0.161  1.00  0.00           O  
HETATM    4  O   UNL     1       0.510  -0.815  -0.090  1.00  0.00           O  
HETATM    5  P   UNL     1      -0.902  -0.051   0.030  1.00  0.00           P  
HETATM    6  O   UNL     1      -1.080   0.946  -1.221  1.00  0.00           O  
HETATM    7  O   UNL     1      -2.097  -1.129   0.032  1.00  0.00           O  
HETATM    8  O   UNL     1      -0.936   0.727   1.289  1.00  0.00           O  
HETATM    9  H   UNL     1       3.316  -1.004   0.888  1.00  0.00           H  
HETATM   10  H   UNL     1       2.912  -1.593  -0.742  1.00  0.00           H  
HETATM   11  H   UNL     1       3.684  -0.003  -0.536  1.00  0.00           H  
HETATM   12  H   UNL     1      -1.067   0.504  -2.081  1.00  0.00           H  
HETATM   13  H   UNL     1      -2.979  -0.738   0.102  1.00  0.00           H  
CONECT    1    2    9   10   11                                       
CONECT    2    1    3    3    4                                       
CONECT    3    2    2                                                 
CONECT    4    2    5                                                 
CONECT    5    4    6    7    8                                       
CONECT    5    8                                                      
CONECT    6    5   12                                                 
CONECT    7    5   13                                                 
CONECT    8    5    5                                                 
CONECT    9    1                                                      
CONECT   10    1                                                      
CONECT   11    1                                                      
CONECT   12    6                                                      
CONECT   13    7                                                      
MASTER        0    0    0    0    0    0    0    0   13    0   13    0
END

Download
SMILES for HMDB0001494 (Acetylphosphate)
CC(=O)OP(O)(O)=O
Download
INCHI for HMDB0001494 (Acetylphosphate)
InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)
Download
View in JSmolView Stereo Labels
Synonyms
ValueSource
Acetic acid, monoanhydride with phosphoric acidChEBI
Acetyl phosphateChEBI
Acetylphosphoric acidChEBI
Monoacetyl phosphateChEBI
Acetate, monoanhydride with phosphateGenerator
Acetyl phosphoric acidGenerator
Monoacetyl phosphoric acidGenerator
Acetyl-pHMDB
Chemical FormulaC2H5O5P
Average Molecular Weight140.0319
Monoisotopic Molecular Weight139.987459782
IUPAC Name(acetyloxy)phosphonic acid
Traditional Nameacetylphosphate
CAS Registry Number590-54-5
SMILES
CC(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)
InChI KeyLIPOUNRJVLNBCD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyl monophosphates. These are organic compounds containing a monophosphate linked to an acyl group. They have the general structure  R-CO-P(O)(O)OH, R=H or organyl.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassOrganic phosphoric acids and derivatives  
Sub ClassPhosphate esters  
Direct ParentAcyl monophosphates  
Alternative Parents
Substituents
  • Acyl monophosphate
    • 

  • Acetate salt
    • 

  • Carboxylic acid salt
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organic salt
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition
Biological location:
Source:
Process
Naturally occurring process:
Role
Industrial application:
Biological role:
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility17.8 g/LALOGPS
logP-0.92ALOGPS
logP-0.88ChemAxon
logS-0.9ALOGPS
pKa (Strongest Acidic)1.24ChemAxon
pKa (Strongest Basic)-7.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.8 m³·mol⁻¹ChemAxon
Polarizability9.87 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties
Collision Cross Sections
NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available128.00431661259  
DarkChem[M-H]-PredictedNot Available121.70131661259  
AllCCS[M+H]+PredictedNot Available132.79732859911  
AllCCS[M-H]-PredictedNot Available125.15932859911  
Retention Indices
Underivatized
Not Available
Derivatized
Not Available
Spectra
GC-MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9000000000-cfae3a8437091232f5d72017-08-28View Spectrum
LC-MS/MS
Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-004i-9100000000-69d8c7734c01156379c82012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-2f22bf3e8b4d114a56d42012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0ufr-9000000000-55ffd7f2d3597806d4812012-07-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Positivesplash10-0002-9100000000-9815fa392fb818a6fab22017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Positivesplash10-0002-9000000000-f9f47252b65adfe6b7ab2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Positivesplash10-000w-9000000000-aee29878b0aaf31375ca2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  10V, Negativesplash10-004i-9200000000-30c93bbfd1e1c181a0bd2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-004i-9000000000-3f8df70a36020543d1d72017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-004i-9000000000-5ee765f8651dddb71d5c2017-07-26View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  20V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum -  40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-09View Spectrum
NMR
Spectrum TypeDescriptionDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04View Spectrum
2D NMR[1H, 1H] 2D NMR Spectrum (predicted)2012-12-04View Spectrum
2D NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, H2O, predicted)2012-12-05View Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02897  
Phenol Explorer Compound IDNot Available
FooDB IDFDB022653  
KNApSAcK IDC00019559  
Chemspider ID181  
KEGG Compound IDC00227  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6278  
PubChem Compound186  
PDB IDNot Available
ChEBI ID15350  
Food Biomarker OntologyNot Available
VMH IDACTP  
MarkerDB IDNot Available
References
Synthesis ReferenceCostakel, O.; Kitzoulesco, I.  The possibility of acetylphosphate synthesis in cancerous and noncancerous human serum at pH 4.    Rev. sci. Med., Acad. rep. populaire Roumaine  (1960),  5  7-10.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Libeer JC, Scharpe SL, Verkerk RM, Deprettere AJ, Schepens PJ: Simultaneous determination of p-aminobenzoic acid, acetyl-p-aminobenzoic acid and p-aminohippuric acid in serum and urine by capillary gas chromatography with use of a nitrogen-phosphorus detector. Clin Chim Acta. 1981 Sep 10;115(2):119-23. [PubMed:6974621  ] 
  2. Dowling TC, Frye RF, Zemaitis MA: Simultaneous determination of p-aminohippuric acid, acetyl-p-aminohippuric acid and iothalamate in human plasma and urine by high-performance liquid chromatography. J Chromatogr B Biomed Sci Appl. 1998 Sep 25;716(1-2):305-13. [PubMed:9824245  ] 
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212  ] 
Enzymes
  Enzyme Details
1. Acylphosphatase-2
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.

Gene Name:
ACYP2
Uniprot ID:
P14621  
Molecular weight:
11139.52
Reactions
Acetylphosphate + Water → Acetic acid + Phosphatedetails
  Enzyme Details
2. Acylphosphatase-1
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.

Gene Name:
ACYP1
Uniprot ID:
P07311  
Molecular weight:
11260.84
Reactions
Acetylphosphate + Water → Acetic acid + Phosphatedetails