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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:43:55 UTC

Update Date

2021-09-26 22:55:58 UTC

HMDB ID

HMDB0246715

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-(2-Aminopropyl)-2-methylphenol

Description

5-(2-Aminopropyl)-2-methylphenol, also known as 4, alpha-dimethyl-3-tyramine, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. Based on a literature review very few articles have been published on 5-(2-Aminopropyl)-2-methylphenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 5-(2-aminopropyl)-2-methylphenol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 5-(2-Aminopropyl)-2-methylphenol 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   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      -1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0246715
HETATM    1  C1  UNL     1      -3.964   0.334  -0.102  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.515  -0.009   0.028  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.910  -0.904  -0.825  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.574  -1.234  -0.723  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.228  -0.676   0.253  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.668  -1.015   0.383  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.547  -0.097  -0.434  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.338   1.328   0.053  1.00  0.00           C  
HETATM    9  N1  UNL     1       3.926  -0.449  -0.118  1.00  0.00           N  
HETATM   10  C9  UNL     1      -0.384   0.221   1.107  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.719   0.551   1.004  1.00  0.00           C  
HETATM   12  O1  UNL     1      -2.281   1.460   1.892  1.00  0.00           O  
HETATM   13  H1  UNL     1      -4.570  -0.125   0.716  1.00  0.00           H  
HETATM   14  H2  UNL     1      -4.361   0.024  -1.074  1.00  0.00           H  
HETATM   15  H3  UNL     1      -4.071   1.442   0.048  1.00  0.00           H  
HETATM   16  H4  UNL     1      -2.550  -1.341  -1.594  1.00  0.00           H  
HETATM   17  H5  UNL     1      -0.123  -1.942  -1.409  1.00  0.00           H  
HETATM   18  H6  UNL     1       1.881  -2.076   0.153  1.00  0.00           H  
HETATM   19  H7  UNL     1       1.976  -0.873   1.450  1.00  0.00           H  
HETATM   20  H8  UNL     1       2.336  -0.157  -1.517  1.00  0.00           H  
HETATM   21  H9  UNL     1       3.201   1.918  -0.346  1.00  0.00           H  
HETATM   22  H10 UNL     1       2.471   1.321   1.167  1.00  0.00           H  
HETATM   23  H11 UNL     1       1.367   1.721  -0.265  1.00  0.00           H  
HETATM   24  H12 UNL     1       4.027  -0.359   0.918  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.019  -1.465  -0.353  1.00  0.00           H  
HETATM   26  H14 UNL     1       0.267   0.657   1.878  1.00  0.00           H  
HETATM   27  H15 UNL     1      -3.230   1.746   1.881  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3    3   11
CONECT    3    4   16
CONECT    4    5    5   17
CONECT    5    6   10
CONECT    6    7   18   19
CONECT    7    8    9   20
CONECT    8   21   22   23
CONECT    9   24   25
CONECT   10   11   11   26
CONECT   11   12
CONECT   12   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4, alpha-Dimethyl-3-tyramine	HMDB
4, alpha-Dimethyl-3-tyramine hydrochloride	HMDB
4, alpha-Dimethyl-m-tyramine	HMDB
4, alpha-Dimethylmetatyramine	HMDB

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.236

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

5-(2-aminopropyl)-2-methylphenol

Traditional Name

5-(2-aminopropyl)-2-methylphenol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C10H15NO/c1-7-3-4-9(5-8(2)11)6-10(7)12/h3-4,6,8,12H,5,11H2,1-2H3

InChI Key

XWLXNPMITZDCHL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenethylamines

Direct Parent

Amphetamines and derivatives

Alternative Parents

Substituents

Amphetamine or derivatives
Phenylpropane
O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Aralkylamine
Toluene
Amine
Primary amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
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	0.96	ALOGPS
logP	1.58	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	10.57	ChemAxon
pKa (Strongest Basic)	9.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.73 m³·mol⁻¹	ChemAxon
Polarizability	19.24 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]+	142.353	30932474
DeepCCS	[M-H]-	138.928	30932474
DeepCCS	[M-2H]-	176.2	30932474
DeepCCS	[M+Na]+	151.738	30932474
AllCCS	[M+H]+	139.1	32859911
AllCCS	[M+H-H2O]+	134.9	32859911
AllCCS	[M+NH4]+	143.0	32859911
AllCCS	[M+Na]+	144.1	32859911
AllCCS	[M-H]-	138.4	32859911
AllCCS	[M+Na-2H]-	139.8	32859911
AllCCS	[M+HCOO]-	141.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(2-Aminopropyl)-2-methylphenol	CC(N)CC1=CC(O)=C(C)C=C1	2430.6	Standard polar	33892256
5-(2-Aminopropyl)-2-methylphenol	CC(N)CC1=CC(O)=C(C)C=C1	1495.9	Standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol	CC(N)CC1=CC(O)=C(C)C=C1	1540.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(2-Aminopropyl)-2-methylphenol,2TMS,isomer #1	CC1=CC=C(CC(C)N[Si](C)(C)C)C=C1O[Si](C)(C)C	1681.8	Semi standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TMS,isomer #1	CC1=CC=C(CC(C)N[Si](C)(C)C)C=C1O[Si](C)(C)C	1676.3	Standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TMS,isomer #1	CC1=CC=C(CC(C)N[Si](C)(C)C)C=C1O[Si](C)(C)C	1795.5	Standard polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TMS,isomer #2	CC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1O	1842.5	Semi standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TMS,isomer #2	CC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1O	1868.7	Standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TMS,isomer #2	CC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1O	1979.0	Standard polar	33892256
5-(2-Aminopropyl)-2-methylphenol,3TMS,isomer #1	CC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	1880.1	Semi standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,3TMS,isomer #1	CC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	1850.0	Standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,3TMS,isomer #1	CC1=CC=C(CC(C)N([Si](C)(C)C)[Si](C)(C)C)C=C1O[Si](C)(C)C	1821.2	Standard polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TBDMS,isomer #1	CC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2157.2	Semi standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TBDMS,isomer #1	CC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2124.5	Standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TBDMS,isomer #1	CC1=CC=C(CC(C)N[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2088.3	Standard polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TBDMS,isomer #2	CC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2280.1	Semi standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TBDMS,isomer #2	CC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2279.8	Standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,2TBDMS,isomer #2	CC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O	2165.1	Standard polar	33892256
5-(2-Aminopropyl)-2-methylphenol,3TBDMS,isomer #1	CC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2576.1	Semi standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,3TBDMS,isomer #1	CC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2455.0	Standard non polar	33892256
5-(2-Aminopropyl)-2-methylphenol,3TBDMS,isomer #1	CC1=CC=C(CC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2180.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9600000000-7aa5eeec4eef8744d72e	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol 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 - 5-(2-Aminopropyl)-2-methylphenol 10V, Positive-QTOF	splash10-00kb-0900000000-f82484f021f93890ff43	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol 20V, Positive-QTOF	splash10-0kfx-3900000000-28e2cc371288c1ab819c	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol 40V, Positive-QTOF	splash10-0kdl-9700000000-f8fcfd590facb336552b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol 10V, Negative-QTOF	splash10-0229-0900000000-3e8470b8215ee0df050e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol 20V, Negative-QTOF	splash10-006x-5900000000-cdff069097571491edf9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(2-Aminopropyl)-2-methylphenol 40V, Negative-QTOF	splash10-00di-2900000000-3dbbdb20857c4460a0e5	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

146955

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

167995

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 5-(2-Aminopropyl)-2-methylphenol (HMDB0246715)

MOL for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

3D MOL for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

3D SDF for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

3D-SDF for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

PDB for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

3D PDB for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

SMILES for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

INCHI for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

Structure for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

3D Structure for HMDB0246715 (5-(2-Aminopropyl)-2-methylphenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra