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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:35 UTC

Update Date

2022-03-07 02:53:07 UTC

HMDB ID

HMDB0031806

Secondary Accession Numbers

HMDB31806

Metabolite Identification

Common Name

(±)-Naled

Description

(±)-Naled, also known as dibrom or bromex, 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. Based on a literature review very few articles have been published on (±)-Naled.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 28-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUL-20         0                                  
HETATM    1  C   UNK     0       2.874  -1.897   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.104   4.771   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0       4.414   3.437   0.000  0.00  0.00          Br+0
HETATM    6 Br   UNK     0       1.334   6.105   0.000  0.00  0.00          Br+0
HETATM    7 Cl   UNK     0       3.437   5.541   0.000  0.00  0.00          Cl+0
HETATM    8 Cl   UNK     0       0.770   4.001   0.000  0.00  0.00          Cl+0
HETATM    9  O   UNK     0       4.207   1.540   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.644  -0.564   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.104   2.104   0.000  0.00  0.00           O+0
HETATM   13  P   UNK     0       2.874   0.770   0.000  0.00  0.00           P+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3    4    5   12                                                  
CONECT    4    3    6    7    8                                             
CONECT    5    3                                                            
CONECT    6    4                                                            
CONECT    7    4                                                            
CONECT    8    4                                                            
CONECT    9   13                                                            
CONECT   10    1   13                                                       
CONECT   11    2   13                                                       
CONECT   12    3   13                                                       
CONECT   13    9   10   11   12                                             
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bromex	ChEBI
Dibrom	ChEBI
Dimethyl-1,2-dibromo-2,2-dichloroethyl phosphate	ChEBI
O,O-Dimethyl O-2,2-dichloro-1,2-dibromoethyl phosphate	ChEBI
O-(1,2-Dibromo-2,2-dichloroethyl)-O,O-dimethyl phosphate	ChEBI
Ortho-dibrom	ChEBI
Phosphoric acid, 1,2-dibromo-2,2-dichloroethyl dimethyl ester	ChEBI
Dimethyl-1,2-dibromo-2,2-dichloroethyl phosphoric acid	Generator
O,O-Dimethyl O-2,2-dichloro-1,2-dibromoethyl phosphoric acid	Generator
O-(1,2-Dibromo-2,2-dichloroethyl)-O,O-dimethyl phosphoric acid	Generator
Phosphate, 1,2-dibromo-2,2-dichloroethyl dimethyl ester	Generator

Chemical Formula

C₄H₇Br₂Cl₂O₄P

Average Molecular Weight

380.784

Monoisotopic Molecular Weight

377.782575932

IUPAC Name

1,2-dibromo-2,2-dichloroethyl dimethyl phosphate

Traditional Name

naled

CAS Registry Number

Not Available

SMILES

COP(=O)(OC)OC(Br)C(Cl)(Cl)Br

InChI Identifier

InChI=1S/C4H7Br2Cl2O4P/c1-10-13(9,11-2)12-3(5)4(6,7)8/h3H,1-2H3

InChI Key

BUYMVQAILCEWRR-UHFFFAOYSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Trialkyl phosphates

Alternative Parents

Substituents

Trialkyl phosphate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organobromide
Organohalogen compound
Alkyl halide
Alkyl chloride
Alkyl bromide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organobromine compound (CHEBI:38729 )
organochlorine compound (CHEBI:38729 )
dialkyl phosphate (CHEBI:38729 )
organophosphate insecticide (CHEBI:38729 )
Organophosphorus insecticides (C18749 )

Ontology

Physiological effect

Health effect

Digestive system disorder

Gastrointestinal disorder

Vomiting (HMDB: HMDB0031806)
Nausea (HMDB: HMDB0031806)

Circulatory system disorder

Vascular disorder

Hypertension (HMDB: HMDB0031806)
Hypotension (HMDB: HMDB0031806)

Nervous system disorder

Headache (HMDB: HMDB0031806)
Tremor (HMDB: HMDB0031806)

Central nervous system disorder

Psychiatric disorder

Depression (HMDB: HMDB0031806)
Anxiety (HMDB: HMDB0031806)

Disposition

Biological location

Cellular substructure

Route of exposure

Parenteral

Dermal (HMDB: HMDB0031806)
Inhalation (HMDB: HMDB0031806)

Enteral

Ingestion (HMDB: HMDB0031806)

Source

Exogenous

Food

Food (HMDB: HMDB0031806)

Synthetic

Synthetic (HMDB: HMDB0031806)

Endogenous

Endogenous (HMDB: HMDB0031806)

Process

Not Available

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	26 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.09 g/L	ALOGPS
logP	2.43	ALOGPS
logP	2.65	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-9.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	58.25 m³·mol⁻¹	ChemAxon
Polarizability	23.5 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	145.775	30932474
DeepCCS	[M-H]-	143.358	30932474
DeepCCS	[M-2H]-	178.694	30932474
DeepCCS	[M+Na]+	153.978	30932474
AllCCS	[M+H]+	156.6	32859911
AllCCS	[M+H-H2O]+	154.2	32859911
AllCCS	[M+NH4]+	158.9	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	159.9	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(??)-Naled	COP(=O)(OC)OC(Br)C(Cl)(Cl)Br	1916.7	Standard polar	33892256
(??)-Naled	COP(=O)(OC)OC(Br)C(Cl)(Cl)Br	1650.8	Standard non polar	33892256
(??)-Naled	COP(=O)(OC)OC(Br)C(Cl)(Cl)Br	1659.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Naled GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-3972000000-70a3d327896ccdec62c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Naled GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (±)-Naled GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-052b-6900000000-0d02b355b355580d8dac	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 10V, Positive-QTOF	splash10-004i-0009000000-7b612c1eb170bb3e820e	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 20V, Positive-QTOF	splash10-004i-0009000000-0be904582f44ade40cc4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 40V, Positive-QTOF	splash10-02bg-1069000000-1b3ed8bc78e87345df77	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 10V, Negative-QTOF	splash10-004i-0009000000-edaae4de24ac4d6d5368	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 20V, Negative-QTOF	splash10-004i-0029000000-5bab263e3b58ef88b2a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 40V, Negative-QTOF	splash10-0297-3079000000-b30ef3e0098348f97622	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 10V, Negative-QTOF	splash10-004i-0009000000-af219a700f16e9b8db7d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 20V, Negative-QTOF	splash10-004i-0009000000-b5901d768035af68d1df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 40V, Negative-QTOF	splash10-004i-0009000000-b92fa398275a419f38c1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 10V, Positive-QTOF	splash10-004i-0009000000-892e28635db4ed3b63ca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 20V, Positive-QTOF	splash10-004i-0109000000-7bc154523ff813cf6ce7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (±)-Naled 40V, Positive-QTOF	splash10-0a6r-1988000000-c397394fb88a80eec232	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB008480

KNApSAcK ID

Not Available

Chemspider ID

4267

KEGG Compound ID

C18749

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Naled

METLIN ID

Not Available

PubChem Compound

4420

PDB ID

Not Available

ChEBI ID

38729

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (±)-Naled (HMDB0031806)

MOL for HMDB0031806 ((±)-Naled)

3D MOL for HMDB0031806 ((±)-Naled)

3D SDF for HMDB0031806 ((±)-Naled)

3D-SDF for HMDB0031806 ((±)-Naled)

PDB for HMDB0031806 ((±)-Naled)

3D PDB for HMDB0031806 ((±)-Naled)

SMILES for HMDB0031806 ((±)-Naled)

INCHI for HMDB0031806 ((±)-Naled)

Structure for HMDB0031806 ((±)-Naled)

3D Structure for HMDB0031806 ((±)-Naled)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra