Np mrd loader

Showing NP-Card for Acetylphosphate (NP0000681)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:47:05 UTC
NP-MRD IDNP0000681
Secondary Accession NumbersNone
Natural Product 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
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000681 (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 NP0000681 (Acetylphosphate)

HMDB0001494
     RDKit          3D
Acetylphosphate
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.3761    0.2928   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806    0.2766    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6915    0.8139    1.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -0.3257   -0.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574   -0.3368    0.2051 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.6747   -0.8798    1.6278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4313    1.1318    0.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419   -1.4697   -0.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0635    0.5073    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    1.0301   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674   -0.7107   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607    1.9165    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642   -2.2465   -0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

3D SDF for NP0000681 (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>
NP0000681

> <DATABASE_NAME>
NP-MRD

> <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 NP0000681 (Acetylphosphate)

HMDB0001494
     RDKit          3D
Acetylphosphate
 13 12  0  0  0  0  0  0  0  0999 V2000
    2.3761    0.2928   -0.2853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806    0.2766    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6915    0.8139    1.3658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0685   -0.3257   -0.4252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6574   -0.3368    0.2051 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.6747   -0.8798    1.6278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4313    1.1318    0.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5419   -1.4697   -0.7262 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0635    0.5073    0.5589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5195    1.0301   -1.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5674   -0.7107   -0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8607    1.9165    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9642   -2.2465   -0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  5  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

PDB for NP0000681 (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 NP0000681 (Acetylphosphate)

COMPND    HMDB0001494
HETATM    1  C1  UNL     1       2.376   0.293  -0.285  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.981   0.277   0.256  1.00  0.00           C  
HETATM    3  O1  UNL     1       0.692   0.814   1.366  1.00  0.00           O  
HETATM    4  O2  UNL     1      -0.069  -0.326  -0.425  1.00  0.00           O  
HETATM    5  P1  UNL     1      -1.657  -0.337   0.205  1.00  0.00           P  
HETATM    6  O3  UNL     1      -1.675  -0.880   1.628  1.00  0.00           O  
HETATM    7  O4  UNL     1      -2.431   1.132   0.066  1.00  0.00           O  
HETATM    8  O5  UNL     1      -2.542  -1.470  -0.726  1.00  0.00           O  
HETATM    9  H1  UNL     1       3.063   0.507   0.559  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.520   1.030  -1.076  1.00  0.00           H  
HETATM   11  H3  UNL     1       2.567  -0.711  -0.725  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.861   1.916   0.091  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.964  -2.247  -0.932  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6    6    7    8
CONECT    7   12
CONECT    8   13
END
Download

SMILES for NP0000681 (Acetylphosphate)

CC(=O)OP(O)(O)=O
Download

INCHI for NP0000681 (Acetylphosphate)

InChI=1S/C2H5O5P/c1-2(3)7-8(4,5)6/h1H3,(H2,4,5,6)
Download
View in JSmol
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 Mass140.0319 Da
Monoisotopic Mass139.98746 Da
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
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Escherichia coli KO11KNApSAcK Database
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
HMDB IDHMDB0001494
DrugBank IDDB02897
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  4. Akyilmaz E, Yorganci E: A novel biosensor based on activation effect of thiamine on the activity of pyruvate oxidase. Biosens Bioelectron. 2008 Jul 15;23(12):1874-7. doi: 10.1016/j.bios.2008.03.001. Epub 2008 Mar 14. [PubMed:18430561 ]
  5. BENTLEY R: A new synthesis of acetyl dihydrogen phosphate. J Am Chem Soc. 1948 Jun;70(6):2183-5. doi: 10.1021/ja01186a057. [PubMed:18863815 ]