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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:56:32 UTC

Update Date

2021-09-26 23:08:38 UTC

HMDB ID

HMDB0254564

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Methyl 2-amino-3-(4-chlorophenyl)propanoate

Description

Methyl 2-amino-3-(4-chlorophenyl)propanoate, also known as 4-chlorophenylalanine methyl ester, belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on Methyl 2-amino-3-(4-chlorophenyl)propanoate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methyl 2-amino-3-(4-chlorophenyl)propanoate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methyl 2-amino-3-(4-chlorophenyl)propanoate 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


  Mrv1652309112115562D          

 14 14  0  0  0  0            999 V2000
    0.0000   -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
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.1250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 N   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254564

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C(N)CC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12ClNO2/c1-14-10(13)9(12)6-7-2-4-8(11)5-3-7/h2-5,9H,6,12H2,1H3

> <INCHI_KEY>
FBHPVOLRIXZZMD-UHFFFAOYSA-N

> <FORMULA>
C10H12ClNO2

> <MOLECULAR_WEIGHT>
213.66

> <EXACT_MASS>
213.0556563

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.72040780653784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-amino-3-(4-chlorophenyl)propanoate

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.8275537853333337

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
6.95764381883255

> <JCHEM_POLAR_SURFACE_AREA>
52.32

> <JCHEM_REFRACTIVITY>
54.6902

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-amino-3-(4-chlorophenyl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0      10.669  -7.700   0.000  0.00  0.00          Cl+0
HETATM   14  N   UNK     0       4.001  -6.930   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   10                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0254564
HETATM    1  C1  UNL     1       3.243  -1.900   0.992  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.821  -0.767   0.271  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.597  -0.158   0.431  1.00  0.00           C  
HETATM    4  O2  UNL     1       0.804  -0.639   1.269  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.172   1.035  -0.338  1.00  0.00           C  
HETATM    6  N1  UNL     1       2.296   1.378  -1.229  1.00  0.00           N  
HETATM    7  C4  UNL     1      -0.006   0.783  -1.220  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.218   0.351  -0.547  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.420  -1.005  -0.376  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.561  -1.493   0.263  1.00  0.00           C  
HETATM   11  C8  UNL     1      -3.516  -0.642   0.738  1.00  0.00           C  
HETATM   12 CL1  UNL     1      -4.923  -1.283   1.527  1.00  0.00          CL  
HETATM   13  C9  UNL     1      -3.331   0.724   0.576  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.197   1.189  -0.057  1.00  0.00           C  
HETATM   15  H1  UNL     1       2.902  -1.877   2.050  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.001  -2.848   0.488  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.364  -1.832   1.049  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.072   1.868   0.353  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.212   0.871  -2.143  1.00  0.00           H  
HETATM   20  H6  UNL     1       3.209   1.153  -0.788  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.222   1.698  -1.796  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.291   0.012  -1.966  1.00  0.00           H  
HETATM   23  H9  UNL     1      -0.727  -1.763  -0.715  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.703  -2.562   0.388  1.00  0.00           H  
HETATM   25  H11 UNL     1      -4.089   1.399   0.953  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.071   2.256  -0.174  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    7   18
CONECT    6   19   20
CONECT    7    8   21   22
CONECT    8    9    9   14
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   13
CONECT   13   14   14   25
CONECT   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl 2-amino-3-(4-chlorophenyl)propanoic acid	Generator
4-Chlorophenylalanine methyl ester	MeSH
4-Chlorophenylalanine methyl ester, (DL)-isomer	MeSH
4-Chlorophenylalanine methyl ester, hydrochloride	MeSH
4-Chlorophenylalanine methyl ester, hydrochloride, (D)-isomer	MeSH
4-Chlorophenylalanine methyl ester, hydrochloride, (DL)-isomer	MeSH
p-Chlorophenylalanine methyl ester	MeSH
Para-chlorophenylalanine methyl ester	MeSH

Chemical Formula

C₁₀H₁₂ClNO₂

Average Molecular Weight

213.66

Monoisotopic Molecular Weight

213.0556563

IUPAC Name

methyl 2-amino-3-(4-chlorophenyl)propanoate

Traditional Name

methyl 2-amino-3-(4-chlorophenyl)propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(N)CC1=CC=C(Cl)C=C1

InChI Identifier

InChI=1S/C10H12ClNO2/c1-14-10(13)9(12)6-7-2-4-8(11)5-3-7/h2-5,9H,6,12H2,1H3

InChI Key

FBHPVOLRIXZZMD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylalanine and derivatives. Phenylalanine and derivatives are compounds containing phenylalanine or a derivative thereof resulting from reaction of phenylalanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Phenylalanine and derivatives

Alternative Parents

Substituents

Phenylalanine or derivatives
Alpha-amino acid ester
Amphetamine or derivatives
Aralkylamine
Chlorobenzene
Fatty acid ester
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Organic nitrogen compound
Organohalogen compound
Primary aliphatic amine
Organochloride
Organonitrogen compound
Organooxygen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	1.42	ALOGPS
logP	1.83	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	6.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.69 m³·mol⁻¹	ChemAxon
Polarizability	21.72 Å³	ChemAxon
Number of Rings	1	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]+	145.864	30932474
DeepCCS	[M-H]-	143.506	30932474
DeepCCS	[M-2H]-	178.552	30932474
DeepCCS	[M+Na]+	153.152	30932474
AllCCS	[M+H]+	146.3	32859911
AllCCS	[M+H-H2O]+	142.3	32859911
AllCCS	[M+NH4]+	149.9	32859911
AllCCS	[M+Na]+	151.0	32859911
AllCCS	[M-H]-	146.2	32859911
AllCCS	[M+Na-2H]-	147.0	32859911
AllCCS	[M+HCOO]-	147.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl 2-amino-3-(4-chlorophenyl)propanoate	COC(=O)C(N)CC1=CC=C(Cl)C=C1	2351.5	Standard polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate	COC(=O)C(N)CC1=CC=C(Cl)C=C1	1630.6	Standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate	COC(=O)C(N)CC1=CC=C(Cl)C=C1	1656.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl 2-amino-3-(4-chlorophenyl)propanoate,1TMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N[Si](C)(C)C	1683.6	Semi standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,1TMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N[Si](C)(C)C	1747.3	Standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,1TMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N[Si](C)(C)C	2328.8	Standard polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,2TMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1896.4	Semi standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,2TMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	1906.5	Standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,2TMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N([Si](C)(C)C)[Si](C)(C)C	2253.5	Standard polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,1TBDMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	1916.9	Semi standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,1TBDMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	1971.0	Standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,1TBDMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N[Si](C)(C)C(C)(C)C	2424.6	Standard polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,2TBDMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2347.1	Semi standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,2TBDMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2305.7	Standard non polar	33892256
Methyl 2-amino-3-(4-chlorophenyl)propanoate,2TBDMS,isomer #1	COC(=O)C(CC1=CC=C(Cl)C=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2410.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufr-3900000000-83709d68740d606d0f8e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate 10V, Negative-QTOF	splash10-03fr-0890000000-14f99f77e07732616713	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate 20V, Negative-QTOF	splash10-001i-3910000000-46b0b11d1b4abc373b0b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate 40V, Negative-QTOF	splash10-001i-5900000000-6e850f9b3a872dd91a67	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate 10V, Positive-QTOF	splash10-0udi-0910000000-96287eb2b1240eebedd6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate 20V, Positive-QTOF	splash10-0udi-0900000000-9f7ce0cc39a4a23f2cbc	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl 2-amino-3-(4-chlorophenyl)propanoate 40V, Positive-QTOF	splash10-014i-1900000000-81746e2a217f8046dcfc	2021-10-12	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

24713

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

26532

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 Methyl 2-amino-3-(4-chlorophenyl)propanoate (HMDB0254564)

MOL for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

3D MOL for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

3D SDF for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

3D-SDF for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

PDB for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

3D PDB for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

SMILES for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

INCHI for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

Structure for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

3D Structure for HMDB0254564 (Methyl 2-amino-3-(4-chlorophenyl)propanoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra