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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 11:11:47 UTC

Update Date

2021-09-26 23:06:00 UTC

HMDB ID

HMDB0253026

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Phenylalanine amide

Description

Phenylalanine amide, also known as PHENH2, 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 a significant number of articles have been published on Phenylalanine amide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Phenylalanine amide is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Phenylalanine amide 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

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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0       1.334   6.930   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0      -1.334   3.850   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
L-Phenylalanine amide	HMDB
PheNH2	HMDB
Phenylalanine amide hydrochloride	HMDB
Phenylalanine amide, (R)-isomer	HMDB
Phenylalanine amide, D-(R)-isomer	HMDB

Chemical Formula

C₉H₁₂N₂O

Average Molecular Weight

164.208

Monoisotopic Molecular Weight

164.094963014

IUPAC Name

2-amino-3-phenylpropanamide

Traditional Name

phenylalanine amide

CAS Registry Number

Not Available

SMILES

NC(CC1=CC=CC=C1)C(N)=O

InChI Identifier

InChI=1S/C9H12N2O/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H2,11,12)

InChI Key

OBSIQMZKFXFYLV-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 amide
Amphetamine or derivatives
Aralkylamine
Monocyclic benzene moiety
Fatty amide
Fatty acyl
Benzenoid
Carboxamide group
Primary carboxylic acid amide
Organic nitrogen compound
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
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)

Source

Exogenous

Exogenous (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	-0.1	ALOGPS
logP	0.27	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	16.34	ChemAxon
pKa (Strongest Basic)	8.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.11 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.94 m³·mol⁻¹	ChemAxon
Polarizability	17.57 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]+	137.154	30932474
DeepCCS	[M-H]-	134.839	30932474
DeepCCS	[M-2H]-	170.989	30932474
DeepCCS	[M+Na]+	146.051	30932474
AllCCS	[M+H]+	138.4	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	142.3	32859911
AllCCS	[M+Na]+	143.4	32859911
AllCCS	[M-H]-	135.9	32859911
AllCCS	[M+Na-2H]-	137.1	32859911
AllCCS	[M+HCOO]-	138.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanine amide	NC(CC1=CC=CC=C1)C(N)=O	2796.7	Standard polar	33892256
Phenylalanine amide	NC(CC1=CC=CC=C1)C(N)=O	1476.9	Standard non polar	33892256
Phenylalanine amide	NC(CC1=CC=CC=C1)C(N)=O	1675.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylalanine amide,1TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(N)=O	1684.2	Semi standard non polar	33892256
Phenylalanine amide,1TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(N)=O	1636.7	Standard non polar	33892256
Phenylalanine amide,1TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(N)=O	2500.0	Standard polar	33892256
Phenylalanine amide,1TMS,isomer #2	C[Si](C)(C)NC(=O)C(N)CC1=CC=CC=C1	1667.0	Semi standard non polar	33892256
Phenylalanine amide,1TMS,isomer #2	C[Si](C)(C)NC(=O)C(N)CC1=CC=CC=C1	1625.5	Standard non polar	33892256
Phenylalanine amide,1TMS,isomer #2	C[Si](C)(C)NC(=O)C(N)CC1=CC=CC=C1	2466.3	Standard polar	33892256
Phenylalanine amide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C	1730.3	Semi standard non polar	33892256
Phenylalanine amide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C	1734.0	Standard non polar	33892256
Phenylalanine amide,2TMS,isomer #1	C[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C	2113.7	Standard polar	33892256
Phenylalanine amide,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1)C(N)=O)[Si](C)(C)C	1857.7	Semi standard non polar	33892256
Phenylalanine amide,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1)C(N)=O)[Si](C)(C)C	1853.9	Standard non polar	33892256
Phenylalanine amide,2TMS,isomer #2	C[Si](C)(C)N(C(CC1=CC=CC=C1)C(N)=O)[Si](C)(C)C	2381.7	Standard polar	33892256
Phenylalanine amide,2TMS,isomer #3	C[Si](C)(C)N(C(=O)C(N)CC1=CC=CC=C1)[Si](C)(C)C	1758.6	Semi standard non polar	33892256
Phenylalanine amide,2TMS,isomer #3	C[Si](C)(C)N(C(=O)C(N)CC1=CC=CC=C1)[Si](C)(C)C	1854.1	Standard non polar	33892256
Phenylalanine amide,2TMS,isomer #3	C[Si](C)(C)N(C(=O)C(N)CC1=CC=CC=C1)[Si](C)(C)C	2252.9	Standard polar	33892256
Phenylalanine amide,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C	1830.7	Semi standard non polar	33892256
Phenylalanine amide,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C	1909.3	Standard non polar	33892256
Phenylalanine amide,3TMS,isomer #1	C[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)N([Si](C)(C)C)[Si](C)(C)C	2062.9	Standard polar	33892256
Phenylalanine amide,3TMS,isomer #2	C[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1909.5	Semi standard non polar	33892256
Phenylalanine amide,3TMS,isomer #2	C[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	1887.4	Standard non polar	33892256
Phenylalanine amide,3TMS,isomer #2	C[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C	2099.5	Standard polar	33892256
Phenylalanine amide,4TMS,isomer #1	C[Si](C)(C)N(C(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2047.0	Semi standard non polar	33892256
Phenylalanine amide,4TMS,isomer #1	C[Si](C)(C)N(C(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2052.8	Standard non polar	33892256
Phenylalanine amide,4TMS,isomer #1	C[Si](C)(C)N(C(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2054.0	Standard polar	33892256
Phenylalanine amide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(N)=O	1925.2	Semi standard non polar	33892256
Phenylalanine amide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(N)=O	1898.2	Standard non polar	33892256
Phenylalanine amide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(N)=O	2630.0	Standard polar	33892256
Phenylalanine amide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C(N)CC1=CC=CC=C1	1905.0	Semi standard non polar	33892256
Phenylalanine amide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C(N)CC1=CC=CC=C1	1882.9	Standard non polar	33892256
Phenylalanine amide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C(N)CC1=CC=CC=C1	2580.0	Standard polar	33892256
Phenylalanine amide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	2157.0	Semi standard non polar	33892256
Phenylalanine amide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	2180.4	Standard non polar	33892256
Phenylalanine amide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N[Si](C)(C)C(C)(C)C	2355.2	Standard polar	33892256
Phenylalanine amide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1)C(N)=O)[Si](C)(C)C(C)(C)C	2240.8	Semi standard non polar	33892256
Phenylalanine amide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1)C(N)=O)[Si](C)(C)C(C)(C)C	2273.0	Standard non polar	33892256
Phenylalanine amide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(CC1=CC=CC=C1)C(N)=O)[Si](C)(C)C(C)(C)C	2521.1	Standard polar	33892256
Phenylalanine amide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)C(N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2203.8	Semi standard non polar	33892256
Phenylalanine amide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)C(N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2265.6	Standard non polar	33892256
Phenylalanine amide,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(C(=O)C(N)CC1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2409.4	Standard polar	33892256
Phenylalanine amide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2463.1	Semi standard non polar	33892256
Phenylalanine amide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2503.6	Standard non polar	33892256
Phenylalanine amide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(CC1=CC=CC=C1)C(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2411.1	Standard polar	33892256
Phenylalanine amide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2519.2	Semi standard non polar	33892256
Phenylalanine amide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2481.1	Standard non polar	33892256
Phenylalanine amide,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2433.1	Standard polar	33892256
Phenylalanine amide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2807.2	Semi standard non polar	33892256
Phenylalanine amide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2781.8	Standard non polar	33892256
Phenylalanine amide,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)C(CC1=CC=CC=C1)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2438.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylalanine amide GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9300000000-bb6e5aa25bab4604b8dc	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylalanine amide 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 - Phenylalanine amide 10V, Positive-QTOF	splash10-00xr-0900000000-9be888a868e497289aa8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanine amide 20V, Positive-QTOF	splash10-0006-9400000000-cb9b80e3620dcd0592d0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanine amide 40V, Positive-QTOF	splash10-0006-9200000000-54c8f2063a65aae7b81a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanine amide 10V, Negative-QTOF	splash10-03di-1900000000-c340a4d7d6889c190747	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanine amide 20V, Negative-QTOF	splash10-0006-9200000000-41e7f0c141b77f81f3de	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylalanine amide 40V, Negative-QTOF	splash10-0006-9000000000-f66d1db8c077d7d2357d	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

168417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

194097

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 Phenylalanine amide (HMDB0253026)

MOL for HMDB0253026 (Phenylalanine amide)

3D MOL for HMDB0253026 (Phenylalanine amide)

3D SDF for HMDB0253026 (Phenylalanine amide)

3D-SDF for HMDB0253026 (Phenylalanine amide)

PDB for HMDB0253026 (Phenylalanine amide)

3D PDB for HMDB0253026 (Phenylalanine amide)

SMILES for HMDB0253026 (Phenylalanine amide)

INCHI for HMDB0253026 (Phenylalanine amide)

Structure for HMDB0253026 (Phenylalanine amide)

3D Structure for HMDB0253026 (Phenylalanine amide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra