Np mrd loader

Showing NP-Card for Trimethyl Phosphate (NP0002912)

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Record Information
Version1.0
Created at2020-11-23 19:43:27 UTC
Updated at2021-08-12 19:52:30 UTC
NP-MRD IDNP0002912
Secondary Accession NumbersNone
Natural Product Identification
Common NameTrimethyl Phosphate
Provided ByBMRBBMRB logo
DescriptionTRIMETHYL PHOSPHATE, also known as TMP, belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains. It was first documented in 2006 (PMID: 17083219). Based on a literature review a significant number of articles have been published on TRIMETHYL PHOSPHATE (PMID: 17984079) (PMID: 18409209) (PMID: 34375074) (PMID: 34227360) (PMID: 33783105) (PMID: 33640600).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002912 (Trimethyl Phosphate)


     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
    2.1260   -1.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -0.3718    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0495    0.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0331    0.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275    1.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4529   -1.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8015   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316   -3.0055    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0203   -0.0129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -1.4036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4237    2.0697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    1.8585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219    3.4603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -1.9034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449    0.7939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502    0.1019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  1  9  1  6
  1 10  1  0
  1 11  1  0
  6 12  1  6
  6 13  1  0
  6 14  1  0
  8 15  1  6
  8 16  1  0
  8 17  1  0
M  END
Download

3D MOL for NP0002912 (Trimethyl Phosphate)

NP0002912
     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -0.4994    2.4268    0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820    1.5338    1.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429    0.0108    0.3557 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.2995    0.1603   -1.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -1.0451    0.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -1.3156   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -0.6004    0.9892 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.1069   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2020    1.8794   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049    3.2618    0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4052    2.7678   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613   -0.6244   -0.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5940   -1.2816   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -2.3471   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736   -1.9487   -0.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584   -1.4183    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941   -0.3525   -0.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  6 12  1  0
  6 13  1  0
  6 14  1  0
  8 15  1  0
  8 16  1  0
  8 17  1  0
M  END
Download

3D SDF for NP0002912 (Trimethyl Phosphate)


     RDKit          2D

 17 16  0  0  0  0  0  0  0  0999 V2000
    2.1260   -1.5092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6297   -1.6148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2099   -0.3718    0.0000 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.0495    0.8712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0331    0.4678    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9275    1.9641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4529   -1.2114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8015   -0.5547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316   -3.0055    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0203   -0.0129    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -1.4036    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4237    2.0697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5688    1.8585    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8219    3.4603    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4582   -1.9034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1449    0.7939    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1502    0.1019    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  1  9  1  6
  1 10  1  0
  1 11  1  0
  6 12  1  6
  6 13  1  0
  6 14  1  0
  8 15  1  6
  8 16  1  0
  8 17  1  0
M  END
> <DATABASE_ID>
NP0002912

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COP(=O)(OC)OC

> <INCHI_IDENTIFIER>
InChI=1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3

> <INCHI_KEY>
WVLBCYQITXONBZ-UHFFFAOYSA-N

> <FORMULA>
C3H9O4P

> <MOLECULAR_WEIGHT>
140.0749

> <EXACT_MASS>
140.023845288

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.556111813127611

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl phosphate

> <ALOGPS_LOGP>
-0.61

> <JCHEM_LOGP>
0.11377834533333306

> <ALOGPS_LOGS>
-0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-9.03615483629026

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
28.098800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl phosphate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002912 (Trimethyl Phosphate)

NP0002912
     RDKit          3D

 17 16  0  0  0  0  0  0  0  0999 V2000
   -0.4994    2.4268    0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0820    1.5338    1.1051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1429    0.0108    0.3557 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.2995    0.1603   -1.1286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -1.0451    0.7984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834   -1.3156   -0.1878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6034   -0.6004    0.9892 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.1069   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2020    1.8794   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0049    3.2618    0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4052    2.7678   -0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8613   -0.6244   -0.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5940   -1.2816   -1.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3823   -2.3471   -0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8736   -1.9487   -0.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3584   -1.4183    0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941   -0.3525   -0.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  3  7  1  0
  7  8  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  6 12  1  0
  6 13  1  0
  6 14  1  0
  8 15  1  0
  8 16  1  0
  8 17  1  0
M  END
Download

PDB for NP0002912 (Trimethyl Phosphate)

HEADER    PROTEIN                                 10-FEB-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-FEB-20         0                                  
HETATM    1  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM    8  P   UNK     0       2.874   0.770   0.000  0.00  0.00           P+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    7                                                            
CONECT    4    8                                                            
CONECT    5    1    8                                                       
CONECT    6    2    8                                                       
CONECT    7    3    8                                                       
CONECT    8    4    5    6    7                                             
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END
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3D PDB for NP0002912 (Trimethyl Phosphate)

COMPND    NP0002912
HETATM    1  C1  UNL     1      -0.499   2.427   0.121  1.00  0.00           C  
HETATM    2  O1  UNL     1      -0.082   1.534   1.105  1.00  0.00           O  
HETATM    3  P1  UNL     1       0.143   0.011   0.356  1.00  0.00           P  
HETATM    4  O2  UNL     1       0.300   0.160  -1.129  1.00  0.00           O  
HETATM    5  O3  UNL     1      -1.072  -1.045   0.798  1.00  0.00           O  
HETATM    6  C2  UNL     1      -1.983  -1.316  -0.188  1.00  0.00           C  
HETATM    7  O4  UNL     1       1.603  -0.600   0.989  1.00  0.00           O  
HETATM    8  C3  UNL     1       2.404  -1.107  -0.031  1.00  0.00           C  
HETATM    9  H1  UNL     1      -1.202   1.879  -0.556  1.00  0.00           H  
HETATM   10  H2  UNL     1      -1.005   3.262   0.651  1.00  0.00           H  
HETATM   11  H3  UNL     1       0.405   2.768  -0.443  1.00  0.00           H  
HETATM   12  H4  UNL     1      -2.861  -0.624  -0.103  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.594  -1.282  -1.210  1.00  0.00           H  
HETATM   14  H6  UNL     1      -2.382  -2.347  -0.002  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.874  -1.949  -0.498  1.00  0.00           H  
HETATM   16  H8  UNL     1       3.358  -1.418   0.447  1.00  0.00           H  
HETATM   17  H9  UNL     1       2.594  -0.352  -0.834  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3
CONECT    3    4    4    5    7
CONECT    5    6
CONECT    6   12   13   14
CONECT    7    8
CONECT    8   15   16   17
END
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SMILES for NP0002912 (Trimethyl Phosphate)

COP(=O)(OC)OC
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INCHI for NP0002912 (Trimethyl Phosphate)

InChI=1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3
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View in JSmol
Synonyms
ValueSource
O,O,O-Trimethyl phosphateChEBI
Phosphoric acid, trimethyl esterChEBI
TMPChEBI
TMPAChEBI
TMPOChEBI
Trimethoxyphosphine oxideChEBI
Trimethyl orthophosphateChEBI
O,O,O-Trimethyl phosphoric acidGenerator
Phosphate, trimethyl esterGenerator
Trimethyl orthophosphoric acidGenerator
TRIMETHYL phosphoric acidGenerator
TrimethylphosphateMeSH
Chemical FormulaC3H9O4P
Average Mass140.0749 Da
Monoisotopic Mass140.02385 Da
IUPAC Nametrimethyl phosphate
Traditional Nametrimethyl phosphate
CAS Registry NumberNot Available
SMILES
COP(=O)(OC)OC
InChI Identifier
InChI=1S/C3H9O4P/c1-5-8(4,6-2)7-3/h1-3H3
InChI KeyWVLBCYQITXONBZ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as trialkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly three alkyl chains.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentTrialkyl phosphates
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.61ALOGPS
logP0.11ChemAxon
logS-0.53ALOGPS
pKa (Strongest Basic)-9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity28.1 m³·mol⁻¹ChemAxon
Polarizability11.56 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0259237
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID10101
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrimethyl_phosphate
METLIN IDNot Available
PubChem Compound10541
PDB IDNot Available
ChEBI ID46324
Good Scents IDNot Available
References
General References
  1. Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
  2. Mitra A, DePue LJ, Struss JE, Patel BP, Parkin S, Atwood DA: Mononuclear Schiff base boron halides: synthesis, characterization, and dealkylation of trimethyl phosphate. Inorg Chem. 2006 Nov 13;45(23):9213-24. doi: 10.1021/ic0607890. [PubMed:17083219 ]
  3. Ruan C, Huang H, Rodgers MT: A simple model for metal cation-phosphate interactions in nucleic acids in the gas phase: alkali metal cations and trimethyl phosphate. J Am Soc Mass Spectrom. 2008 Feb;19(2):305-14. doi: 10.1016/j.jasms.2007.10.006. [PubMed:18409209 ]
  4. Li C, Liu G, Wang K, Dong W, Han J, Yu Y, Min Z, Yang C, Lu Z: Electrochemically-Matched and Nonflammable Janus Solid Electrolyte for Lithium-Metal Batteries. ACS Appl Mater Interfaces. 2021 Aug 10. doi: 10.1021/acsami.1c08687. [PubMed:34375074 ]
  5. Hou M, Shi Y, Cai Y: [Determination of 16 organophosphate esters in human blood by high performance liquid chromatography-tandem mass spectrometry combined with liquid-liquid extraction and solid phase extraction]. Se Pu. 2021 Jan;39(1):69-76. doi: 10.3724/SP.J.1123.2020.07033. [PubMed:34227360 ]
  6. Jia H, Xu Y, Zhang X, Burton SD, Gao P, Matthews BE, Engelhard MH, Han KS, Zhong L, Wang C, Xu W: Advanced Low-Flammable Electrolytes for Stable Operation of High-Voltage Lithium-Ion Batteries. Angew Chem Int Ed Engl. 2021 Jun 1;60(23):12999-13006. doi: 10.1002/anie.202102403. Epub 2021 Apr 29. [PubMed:33783105 ]
  7. Soares PRS, Birolli WG, Ferreira IM, Porto ALM: Biodegradation pathway of the organophosphate pesticides chlorpyrifos, methyl parathion and profenofos by the marine-derived fungus Aspergillus sydowii CBMAI 935 and its potential for methylation reactions of phenolic compounds. Mar Pollut Bull. 2021 May;166:112185. doi: 10.1016/j.marpolbul.2021.112185. Epub 2021 Feb 25. [PubMed:33640600 ]
  8. Zhang T, Li Y, Chen N, Wen Z, Shang Y, Zhao Y, Yan M, Guan M, Wu F, Chen R: Regulating the Solvation Structure of Nonflammable Electrolyte for Dendrite-Free Li-Metal Batteries. ACS Appl Mater Interfaces. 2021 Jan 13;13(1):681-687. doi: 10.1021/acsami.0c19075. Epub 2021 Jan 5. [PubMed:33398985 ]
  9. Bouibes A, Saha S, Nagaoka M: Theoretically predicting the feasibility of highly-fluorinated ethers as promising diluents for non-flammable concentrated electrolytes. Sci Rep. 2020 Dec 15;10(1):21966. doi: 10.1038/s41598-020-79038-y. [PubMed:33319821 ]