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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 22:20:03 UTC

Update Date

2021-09-26 22:53:35 UTC

HMDB ID

HMDB0245244

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2-(3-Mercaptopropyl)pentanedioic acid

Description

2-(3-Mercaptopropyl)pentanedioic acid, also known as 2-mppa CPD, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Based on a literature review a significant number of articles have been published on 2-(3-Mercaptopropyl)pentanedioic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2-(3-mercaptopropyl)pentanedioic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2-(3-Mercaptopropyl)pentanedioic 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                                 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      13.598   4.771   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.596   4.771   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.930   2.461   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      10.931   6.311   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.597   7.081   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      12.265   7.081   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   13  S   UNK     0      16.266   4.771   0.000  0.00  0.00           S+0
CONECT    1    2   12                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    3   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0245244
HETATM    1  O1  UNL     1      -4.200   0.677  -1.418  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.653   1.214  -0.436  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.037   2.464  -0.012  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.576   0.486   0.277  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.258   0.591  -0.437  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.219  -0.181   0.347  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.116  -0.026  -0.376  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.222  -0.751   0.316  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.548  -0.581  -0.413  1.00  0.00           C  
HETATM   10  S1  UNL     1       4.065   1.119  -0.546  1.00  0.00           S  
HETATM   11  C8  UNL     1      -0.555  -1.633   0.318  1.00  0.00           C  
HETATM   12  O3  UNL     1      -1.409  -2.039  -0.506  1.00  0.00           O  
HETATM   13  O4  UNL     1       0.010  -2.584   1.138  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.399   3.179   0.314  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.428   0.890   1.312  1.00  0.00           H  
HETATM   16  H3  UNL     1      -2.825  -0.576   0.430  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.307   0.187  -1.477  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.895   1.649  -0.492  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.208   0.225   1.370  1.00  0.00           H  
HETATM   20  H7  UNL     1       0.982  -0.454  -1.379  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.323   1.071  -0.428  1.00  0.00           H  
HETATM   22  H9  UNL     1       2.366  -0.424   1.370  1.00  0.00           H  
HETATM   23  H10 UNL     1       2.028  -1.839   0.298  1.00  0.00           H  
HETATM   24  H11 UNL     1       3.493  -1.123  -1.385  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.303  -1.127   0.223  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.075   2.005  -0.952  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.437  -2.417   2.031  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7   11   19
CONECT    7    8   20   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   26
CONECT   11   12   12   13
CONECT   13   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-(3-Mercaptopropyl)pentanedioate	Generator
2-MPPA CPD	HMDB

Chemical Formula

C₈H₁₄O₄S

Average Molecular Weight

206.26

Monoisotopic Molecular Weight

206.061280105

IUPAC Name

2-(3-sulfanylpropyl)pentanedioic acid

Traditional Name

2-(3-sulfanylpropyl)pentanedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CCC(CCCS)C(O)=O

InChI Identifier

InChI=1S/C8H14O4S/c9-7(10)4-3-6(8(11)12)2-1-5-13/h6,13H,1-5H2,(H,9,10)(H,11,12)

InChI Key

FNLNSQHJKVQCBP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-chain fatty acids

Alternative Parents

Substituents

Medium-chain fatty acid
Thia fatty acid
Branched fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Alkylthiol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	0.84	ALOGPS
logP	1.29	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	49.87 m³·mol⁻¹	ChemAxon
Polarizability	21.09 Å³	ChemAxon
Number of Rings	0	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]+	143.789	30932474
DeepCCS	[M-H]-	139.961	30932474
DeepCCS	[M-2H]-	177.042	30932474
DeepCCS	[M+Na]+	152.707	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-(3-Mercaptopropyl)pentanedioic acid	OC(=O)CCC(CCCS)C(O)=O	2933.5	Standard polar	33892256
2-(3-Mercaptopropyl)pentanedioic acid	OC(=O)CCC(CCCS)C(O)=O	1599.9	Standard non polar	33892256
2-(3-Mercaptopropyl)pentanedioic acid	OC(=O)CCC(CCCS)C(O)=O	1759.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-(3-Mercaptopropyl)pentanedioic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(CCCS[Si](C)(C)C)C(=O)O[Si](C)(C)C	2048.5	Semi standard non polar	33892256
2-(3-Mercaptopropyl)pentanedioic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(CCCS[Si](C)(C)C)C(=O)O[Si](C)(C)C	2037.4	Standard non polar	33892256
2-(3-Mercaptopropyl)pentanedioic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)CCC(CCCS[Si](C)(C)C)C(=O)O[Si](C)(C)C	2094.0	Standard polar	33892256
2-(3-Mercaptopropyl)pentanedioic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(CCCS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2715.6	Semi standard non polar	33892256
2-(3-Mercaptopropyl)pentanedioic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(CCCS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2665.1	Standard non polar	33892256
2-(3-Mercaptopropyl)pentanedioic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CCC(CCCS[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2484.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-03dm-7900000000-045033ef77b759385434	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid GC-MS (TBDMS_2_3) - 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 - 2-(3-Mercaptopropyl)pentanedioic acid 10V, Positive-QTOF	splash10-0550-0910000000-429b2c253914cba9715a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid 20V, Positive-QTOF	splash10-0itm-4900000000-d87889cc644c241d128e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid 40V, Positive-QTOF	splash10-0550-9000000000-d438a5c8c2e9d096b7f5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid 10V, Negative-QTOF	splash10-0c29-0920000000-6356ff3cab0846a87e02	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid 20V, Negative-QTOF	splash10-0btc-1910000000-e470c6da522fd73d4f01	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-(3-Mercaptopropyl)pentanedioic acid 40V, Negative-QTOF	splash10-052f-9400000000-05eff7a8030715d0e558	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)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-12	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	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

8373671

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10198171

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 2-(3-Mercaptopropyl)pentanedioic acid (HMDB0245244)

MOL for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

3D MOL for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

3D SDF for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

3D-SDF for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

PDB for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

3D PDB for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

SMILES for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

INCHI for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

Structure for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

3D Structure for HMDB0245244 (2-(3-Mercaptopropyl)pentanedioic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra