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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:22:26 UTC

Update Date

2021-09-26 22:55:22 UTC

HMDB ID

HMDB0246346

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Amino-3-phenylbutanoic acid

Description

4-Amino-3-phenylbutanoic acid, also known as fenibut or noophen, belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Based on a literature review very few articles have been published on 4-Amino-3-phenylbutanoic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-amino-3-phenylbutanoic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Amino-3-phenylbutanoic acid 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                                 23-JUN-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-17         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  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       4.001   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   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
4-Amino-3-phenylbutanoate	Generator
Fenibut	HMDB
4-Amino-3-phenylbutyric acid hydrochloride	HMDB
Noophen	HMDB
Citrocard	HMDB
4-Amino-3-phenylbutyric acid, (DL)-(+-)-mixture	HMDB
4-Amino-3-phenylbutyric acid	HMDB
beta-(Aminomethyl)benzenepropanoic acid	HMDB
Phenyl-gaba	HMDB
4-Amino-3-phenylbutyric acid, (L)-(-)-isomer	HMDB
Fenibut citrate	HMDB
beta-Phenyl-gamma-aminobutyric acid	HMDB
Phenybut	HMDB
beta-(Aminomethyl)hydrocinnamic acid	HMDB
Phenibut	MeSH

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Weight

179.219

Monoisotopic Molecular Weight

179.094628663

IUPAC Name

4-amino-3-phenylbutanoic acid

Traditional Name

phenibut

CAS Registry Number

Not Available

SMILES

NCC(CC(O)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C10H13NO2/c11-7-9(6-10(12)13)8-4-2-1-3-5-8/h1-5,9H,6-7,11H2,(H,12,13)

InChI Key

DAFOCGYVTAOKAJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
3-phenylpropanoic-acid
Amino fatty acid
Aralkylamine
Monocyclic benzene moiety
Benzenoid
Fatty acyl
Amino acid
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Organopnictogen compound
Amine
Carbonyl group
Organic oxygen compound
Primary amine
Hydrocarbon derivative
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	-1.3	ALOGPS
logP	-1.4	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	9.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	63.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	50.02 m³·mol⁻¹	ChemAxon
Polarizability	18.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	137.636	30932474
DeepCCS	[M-H]-	134.215	30932474
DeepCCS	[M-2H]-	171.269	30932474
DeepCCS	[M+Na]+	146.807	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	135.4	32859911
AllCCS	[M+NH4]+	143.5	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	139.9	32859911
AllCCS	[M+Na-2H]-	140.8	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-3-phenylbutanoic acid	NCC(CC(O)=O)C1=CC=CC=C1	2843.8	Standard polar	33892256
4-Amino-3-phenylbutanoic acid	NCC(CC(O)=O)C1=CC=CC=C1	1651.2	Standard non polar	33892256
4-Amino-3-phenylbutanoic acid	NCC(CC(O)=O)C1=CC=CC=C1	1697.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Amino-3-phenylbutanoic acid,2TMS,isomer #1	C[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C)C1=CC=CC=C1	1721.9	Semi standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TMS,isomer #1	C[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C)C1=CC=CC=C1	1804.5	Standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TMS,isomer #1	C[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C)C1=CC=CC=C1	2099.8	Standard polar	33892256
4-Amino-3-phenylbutanoic acid,2TMS,isomer #2	C[Si](C)(C)N(CC(CC(=O)O)C1=CC=CC=C1)[Si](C)(C)C	1945.0	Semi standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TMS,isomer #2	C[Si](C)(C)N(CC(CC(=O)O)C1=CC=CC=C1)[Si](C)(C)C	1949.2	Standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TMS,isomer #2	C[Si](C)(C)N(CC(CC(=O)O)C1=CC=CC=C1)[Si](C)(C)C	2238.8	Standard polar	33892256
4-Amino-3-phenylbutanoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	1954.2	Semi standard non polar	33892256
4-Amino-3-phenylbutanoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	1965.6	Standard non polar	33892256
4-Amino-3-phenylbutanoic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2075.1	Standard polar	33892256
4-Amino-3-phenylbutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2208.1	Semi standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2237.7	Standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(CC(=O)O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2359.4	Standard polar	33892256
4-Amino-3-phenylbutanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(CC(=O)O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2411.5	Semi standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(CC(=O)O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2327.2	Standard non polar	33892256
4-Amino-3-phenylbutanoic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CC(CC(=O)O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2430.2	Standard polar	33892256
4-Amino-3-phenylbutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2644.5	Semi standard non polar	33892256
4-Amino-3-phenylbutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2547.5	Standard non polar	33892256
4-Amino-3-phenylbutanoic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2406.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-3-phenylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9600000000-75e483bce20b124a96ad	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-3-phenylbutanoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-3-phenylbutanoic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-3-phenylbutanoic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-3-phenylbutanoic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Amino-3-phenylbutanoic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 4-Amino-3-phenylbutanoic acid 10V, Positive-QTOF	splash10-01q9-0900000000-cbdc5e72ef909139d326	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 20V, Positive-QTOF	splash10-01q9-0900000000-7c685aa202832dc80bc0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 40V, Positive-QTOF	splash10-0udi-2900000000-0edc020b442605311db8	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 10V, Negative-QTOF	splash10-0059-0900000000-52895fbfbde2460a1623	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 20V, Negative-QTOF	splash10-0059-0900000000-e725037bff936a0a7506	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 40V, Negative-QTOF	splash10-05r0-5900000000-86039882b15571a4427f	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 10V, Positive-QTOF	splash10-03xs-0900000000-c767960bb39ce812ff76	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 20V, Positive-QTOF	splash10-014i-2900000000-d7f3ee2df9f111f353cd	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 40V, Positive-QTOF	splash10-0gbc-6900000000-6c611bd0499bf43ba484	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 10V, Negative-QTOF	splash10-01u0-0900000000-07c6b60ebfb2f621b92b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 20V, Negative-QTOF	splash10-0pxr-2900000000-5453f52ae777dc236f2b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Amino-3-phenylbutanoic acid 40V, Negative-QTOF	splash10-00or-9400000000-670be80041a3b0aa9f01	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)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-13	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

DB13455

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

13491

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenibut

METLIN ID

Not Available

PubChem Compound

14113

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-Amino-3-phenylbutanoic acid (HMDB0246346)

MOL for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

3D MOL for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

3D SDF for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

3D-SDF for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

PDB for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

3D PDB for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

SMILES for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

INCHI for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

Structure for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

3D Structure for HMDB0246346 (4-Amino-3-phenylbutanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra