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Showing metabocard for Phosphoryl chloride (HMDB0034789)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:42:49 UTC
Update Date2023-02-21 17:24:23 UTC
HMDB IDHMDB0034789
Secondary Accession Numbers
  • HMDB34789
Metabolite Identification
Common NamePhosphoryl chloride
DescriptionPhosphoryl chloride is an etherification and esterification agent for modification of food starch. Like phosphate, phosphoryl chloride is tetrahedral in shape. It features three P-Cl bonds and one very strong P=O double bond, with an estimated bond dissociation energy of 533.5 kJ/mol. On the basis of bond length and electronegativity, the Schomaker-Stevenson rule suggests that the double bond form is very dominant (in contrast with POF3). The P=O bond does not resemble the bond in a carbonyl group as in a ketone. The appropriate description of the P-O interaction is a matter of long discussion. Older textbooks favor a description that invokes participation of the d-orbitals on phosphorus. Some of these d-orbitals project toward the O atom, overlapping with p-orbitals on oxygen. More modern texts seem to favor a description where the P-O bonding involves the * components of the P-Cl bonds. These descriptions do not consider a role for d-orbitals. Phosphoryl chloride (commonly called phosphorus oxychloride) is a colourless liquid with the formula POCl3. It hydrolyses in moist air to phosphoric acid to release choking fumes of hydrogen chloride. It is manufactured industrially on a large scale from phosphorus trichloride and oxygen or phosphorus pentoxide. It is mainly used to make phosphate esters such as tricresyl phosphate
Structure
Data?1677000263
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0034789 (Phosphoryl chloride)


  Mrv0541 02241220312D          

  5  4  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0034789 (Phosphoryl chloride)

HMDB0034789
     RDKit          3D
Phosphoryl chloride
  5  4  0  0  0  0  0  0  0  0999 V2000
   -0.0210    0.0338    1.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -0.0106    0.1110 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.8209   -0.7467   -0.5507 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387    1.9170   -0.6003 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548   -1.1936   -0.5722 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
M  END
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3D SDF for HMDB0034789 (Phosphoryl chloride)


  Mrv0541 02241220312D          

  5  4  0  0  0  0            999 V2000
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  4  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034789

> <DATABASE_NAME>
hmdb

> <SMILES>
ClP(Cl)(Cl)=O

> <INCHI_IDENTIFIER>
InChI=1S/Cl3OP/c1-5(2,3)4

> <INCHI_KEY>
XHXFXVLFKHQFAL-UHFFFAOYSA-N

> <FORMULA>
Cl3OP

> <MOLECULAR_WEIGHT>
153.332

> <EXACT_MASS>
151.875234255

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
9.437593255997738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phosphoroyl trichloride

> <JCHEM_LOGP>
1.2760851123333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
25.366999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
phosphorus oxychloride

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0034789 (Phosphoryl chloride)

HMDB0034789
     RDKit          3D
Phosphoryl chloride
  5  4  0  0  0  0  0  0  0  0999 V2000
   -0.0210    0.0338    1.6123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0065   -0.0106    0.1110 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.8209   -0.7467   -0.5507 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2387    1.9170   -0.6003 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548   -1.1936   -0.5722 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
M  END
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PDB for HMDB0034789 (Phosphoryl chloride)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    2 Cl   UNK     0       0.000  -1.540   0.000  0.00  0.00          Cl+0
HETATM    3 Cl   UNK     0      -1.540   0.000   0.000  0.00  0.00          Cl+0
HETATM    4  P   UNK     0       0.000   0.000   0.000  0.00  0.00           P+0
HETATM    5 Cl   UNK     0       1.540   0.000   0.000  0.00  0.00          Cl+0
CONECT    1    4                                                            
CONECT    2    4                                                            
CONECT    3    4                                                            
CONECT    4    1    2    3    5                                             
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0034789 (Phosphoryl chloride)

COMPND    HMDB0034789
HETATM    1  O1  UNL     1      -0.021   0.034   1.612  1.00  0.00           O  
HETATM    2  P1  UNL     1      -0.006  -0.011   0.111  1.00  0.00           P  
HETATM    3 CL1  UNL     1       1.821  -0.747  -0.551  1.00  0.00          CL  
HETATM    4 CL2  UNL     1      -0.239   1.917  -0.600  1.00  0.00          CL  
HETATM    5 CL3  UNL     1      -1.555  -1.194  -0.572  1.00  0.00          CL  
CONECT    1    2    2
CONECT    2    3    4    5
END
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SMILES for HMDB0034789 (Phosphoryl chloride)

ClP(Cl)(Cl)=O
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INCHI for HMDB0034789 (Phosphoryl chloride)

InChI=1S/Cl3OP/c1-5(2,3)4
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View in JSmolView Stereo Labels
Synonyms
ValueSource
[PCL3O]ChEBI
Phosphoric trichlorideChEBI
PhosphoroxidchloridChEBI
PhosphoroxychloridChEBI
PhosphortrichloridoxidChEBI
Phosphorus oxychlorideChEBI
Phosphorus trichloride oxideChEBI
Phosphorus(V) trichloride oxideChEBI
PhosphorylchloridChEBI
POCl3ChEBI
Trichlorure de phosphoryleChEBI
FosforoxychloridHMDB
OPCl3HMDB
Oxychlorid fosforecnyHMDB
Phosphoric chlorideHMDB
Phosphorous oxychlorideHMDB
PhosphoroxychlorideHMDB
Phosphorus chlorideHMDB
Phosphorus chloride oxide (pocl3)HMDB
Phosphorus oxide chlorideHMDB
Phosphorus oxide trichlorideHMDB
Phosphorus oxytrichlorideHMDB
Phosphorus(V) oxide chlorideHMDB
Phosphorus(V) oxychlorideHMDB
Phosphoryl trichlorideHMDB
TrichloridooxidophosphorusHMDB
Trichlorooxophosphorus(V)HMDB
Trichlorophosphine oxideHMDB
Trichlorophosphorus oxideHMDB
Phosphoryl chlorideChEBI
Chemical FormulaCl3OP
Average Molecular Weight153.332
Monoisotopic Molecular Weight151.875234255
IUPAC Namephosphoroyl trichloride
Traditional Namephosphorus oxychloride
CAS Registry Number10025-87-3
SMILES
ClP(Cl)(Cl)=O
InChI Identifier
InChI=1S/Cl3OP/c1-5(2,3)4
InChI KeyXHXFXVLFKHQFAL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of inorganic compounds known as halogen oxides. These are inorganic compounds containing an oxygen atom of an oxidation state of -2, in which the heaviest atom bonded to the oxygen is a halogen.
KingdomInorganic compounds
Super ClassHomogeneous non-metal compounds
ClassHalogen organides
Sub ClassHalogen oxides
Direct ParentHalogen oxides
Alternative Parents
Substituents
  • Halogen oxide
  • Inorganic oxide
Molecular FrameworkNot Available
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
Role
Biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point1 - 1.5 °CNot Available
Boiling Point105.00 to 106.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility61970 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP0.357 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility9.33 g/LALOGPS
logP1.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity25.37 m³·mol⁻¹ChemAxon
Polarizability9.44 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+120.87330932474
DeepCCS[M-H]-118.99130932474
DeepCCS[M-2H]-154.39230932474
DeepCCS[M+Na]+128.7230932474
AllCCS[M+H]+129.232859911
AllCCS[M+H-H2O]+125.332859911
AllCCS[M+NH4]+132.832859911
AllCCS[M+Na]+133.832859911
AllCCS[M-H]-148.632859911
AllCCS[M+Na-2H]-154.332859911
AllCCS[M+HCOO]-160.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Phosphoryl chlorideClP(Cl)(Cl)=O1115.8Standard polar33892256
Phosphoryl chlorideClP(Cl)(Cl)=O797.4Standard non polar33892256
Phosphoryl chlorideClP(Cl)(Cl)=O850.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoryl chloride GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0900000000-5c46befa3028eba4a34d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Phosphoryl chloride GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 10V, Positive-QTOFsplash10-0udi-0900000000-8ba138ebff631ad13b8f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 20V, Positive-QTOFsplash10-0udi-0900000000-8ba138ebff631ad13b8f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 40V, Positive-QTOFsplash10-0udi-0900000000-8ba138ebff631ad13b8f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 10V, Negative-QTOFsplash10-0udi-0900000000-dbc9a67946553812d4242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 20V, Negative-QTOFsplash10-0udi-0900000000-dbc9a67946553812d4242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 40V, Negative-QTOFsplash10-0udi-0900000000-dbc9a67946553812d4242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 10V, Positive-QTOFsplash10-0udi-0900000000-a197ffb7b5d9d2598f652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 20V, Positive-QTOFsplash10-0udi-0900000000-a197ffb7b5d9d2598f652021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Phosphoryl chloride 40V, Positive-QTOFsplash10-0gb9-0900000000-24baa9fa82667f75123c2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB013347
KNApSAcK IDNot Available
Chemspider ID23198
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhosphoryl chloride
METLIN IDNot Available
PubChem Compound24813
PDB IDNot Available
ChEBI ID30336
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1274551
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .