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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:04:01 UTC

Update Date

2021-09-26 23:17:54 UTC

HMDB ID

HMDB0260013

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-(4-(Chloromethyl)phenyl)morpholin-3-one

Description

4-[4-(chloromethyl)phenyl]morpholin-3-one belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond. Based on a literature review very few articles have been published on 4-[4-(chloromethyl)phenyl]morpholin-3-one. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-(4-(chloromethyl)phenyl)morpholin-3-one is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-(4-(Chloromethyl)phenyl)morpholin-3-one is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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


  Mrv1652309122101042D          

 15 16  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0260013

> <DATABASE_NAME>
hmdb

> <SMILES>
ClCC1=CC=C(C=C1)N1CCOCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12ClNO2/c12-7-9-1-3-10(4-2-9)13-5-6-15-8-11(13)14/h1-4H,5-8H2

> <INCHI_KEY>
WBSSDSSXNMRUOJ-UHFFFAOYSA-N

> <FORMULA>
C11H12ClNO2

> <MOLECULAR_WEIGHT>
225.67

> <EXACT_MASS>
225.0556563

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
22.743561549630755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[4-(chloromethyl)phenyl]morpholin-3-one

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.3166178550000005

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.85748828546555

> <JCHEM_PKA_STRONGEST_BASIC>
-4.194131271887142

> <JCHEM_POLAR_SURFACE_AREA>
29.54

> <JCHEM_REFRACTIVITY>
58.388200000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[4-(chloromethyl)phenyl]morpholin-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15 Cl   UNK     0      -0.000   4.620   0.000  0.00  0.00          Cl+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    1    8                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0260013
HETATM    1  O1  UNL     1      -1.271  -2.499  -0.038  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.856  -1.419   0.156  1.00  0.00           C  
HETATM    3  C2  UNL     1      -3.298  -1.323   0.589  1.00  0.00           C  
HETATM    4  O2  UNL     1      -3.959  -0.476  -0.252  1.00  0.00           O  
HETATM    5  C3  UNL     1      -3.454   0.767  -0.443  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.021   0.998  -0.141  1.00  0.00           C  
HETATM    7  N1  UNL     1      -1.208  -0.181  -0.014  1.00  0.00           N  
HETATM    8  C5  UNL     1       0.197  -0.075  -0.062  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.972  -0.671  -1.051  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.352  -0.543  -1.064  1.00  0.00           C  
HETATM   11  C8  UNL     1       3.006   0.183  -0.093  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.491   0.339  -0.085  1.00  0.00           C  
HETATM   13 CL1  UNL     1       5.155  -1.007   0.870  1.00  0.00          CL  
HETATM   14  C10 UNL     1       2.272   0.777   0.887  1.00  0.00           C  
HETATM   15  C11 UNL     1       0.904   0.651   0.903  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.771  -2.301   0.597  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.355  -0.917   1.624  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.065   1.486   0.178  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.717   1.072  -1.502  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.919   1.547   0.839  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.607   1.706  -0.916  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.483  -1.245  -1.822  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.981  -0.997  -1.824  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.867   0.357  -1.129  1.00  0.00           H  
HETATM   25  H10 UNL     1       4.751   1.290   0.438  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.748   1.348   1.657  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.322   1.134   1.700  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    7
CONECT    3    4   16   17
CONECT    4    5
CONECT    5    6   18   19
CONECT    6    7   20   21
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   22
CONECT   10   11   11   23
CONECT   11   12   14
CONECT   12   13   24   25
CONECT   14   15   15   26
CONECT   15   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂ClNO₂

Average Molecular Weight

225.67

Monoisotopic Molecular Weight

225.0556563

IUPAC Name

4-[4-(chloromethyl)phenyl]morpholin-3-one

Traditional Name

4-[4-(chloromethyl)phenyl]morpholin-3-one

CAS Registry Number

Not Available

SMILES

ClCC1=CC=C(C=C1)N1CCOCC1=O

InChI Identifier

InChI=1S/C11H12ClNO2/c12-7-9-1-3-10(4-2-9)13-5-6-15-8-11(13)14/h1-4H,5-8H2

InChI Key

WBSSDSSXNMRUOJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylmorpholines. These are aromatic compounds containing a morpholine ring and a benzene ring linked to each other through a CC or a CN bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxazinanes

Sub Class

Morpholines

Direct Parent

Phenylmorpholines

Alternative Parents

Substituents

Phenylmorpholine
Benzyl chloride
Benzyl halide
Monocyclic benzene moiety
Benzenoid
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Carboxylic acid derivative
Dialkyl ether
Ether
Oxacycle
Azacycle
Organonitrogen compound
Organochloride
Organohalogen compound
Organopnictogen compound
Alkyl halide
Alkyl chloride
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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
logP	1.5	ALOGPS
logP	1.32	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	15.86	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	58.39 m³·mol⁻¹	ChemAxon
Polarizability	22.74 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	148.273	32859911
AllCCS	[M+H-H2O]+	144.248	32859911
AllCCS	[M+Na]+	153.095	32859911
AllCCS	[M+NH4]+	152.017	32859911
AllCCS	[M-H]-	150.228	32859911
AllCCS	[M+Na-2H]-	150.539	32859911
AllCCS	[M+HCOO]-	150.973	32859911
DeepCCS	[M+H]+	147.74	30932474
DeepCCS	[M-H]-	143.912	30932474
DeepCCS	[M-2H]-	180.96	30932474
DeepCCS	[M+Na]+	156.498	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-(4-(Chloromethyl)phenyl)morpholin-3-one	ClCC1=CC=C(C=C1)N1CCOCC1=O	2805.8	Standard polar	33892256
4-(4-(Chloromethyl)phenyl)morpholin-3-one	ClCC1=CC=C(C=C1)N1CCOCC1=O	2057.1	Standard non polar	33892256
4-(4-(Chloromethyl)phenyl)morpholin-3-one	ClCC1=CC=C(C=C1)N1CCOCC1=O	2033.0	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 - 4-(4-(Chloromethyl)phenyl)morpholin-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-1900000000-7b6325c0f92eaf7f130e	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-(4-(Chloromethyl)phenyl)morpholin-3-one GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-27	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26550852

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53417739

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 4-(4-(Chloromethyl)phenyl)morpholin-3-one (HMDB0260013)

MOL for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

3D MOL for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

3D SDF for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

3D-SDF for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

PDB for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

3D PDB for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

SMILES for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

INCHI for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

Structure for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

3D Structure for HMDB0260013 (4-(4-(Chloromethyl)phenyl)morpholin-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

NMR Spectra