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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:53:22 UTC

Update Date

2021-09-26 22:52:42 UTC

HMDB ID

HMDB0244752

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetyl-3-(nitrosulfanyl)-L-valine

Description

N-Acetyl-3-(nitrosulfanyl)-L-valine belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Based on a literature review very few articles have been published on N-Acetyl-3-(nitrosulfanyl)-L-valine. This compound has been identified in human blood as reported by (PMID: 31557052 ). N-acetyl-3-(nitrosulfanyl)-l-valine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically N-Acetyl-3-(nitrosulfanyl)-L-valine 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


  Mrv1652309102123532D          

 15 14  0  0  0  0            999 V2000
    2.3155   -0.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587   -1.5071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6883   -0.5163    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2604   -1.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0316   -1.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6036   -2.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307   -2.1016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0612   -0.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2594   -1.7135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8631   -0.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8621   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.4341   -1.3089    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
    7.2350   -1.1108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2053   -2.1016    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
M  CHG  2  13   1  15  -1
M  END
> <DATABASE_ID>
HMDB0244752

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC(C(O)=O)C(C)(C)S[N+]([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12N2O5S/c1-4(10)8-5(6(11)12)7(2,3)15-9(13)14/h5H,1-3H3,(H,8,10)(H,11,12)

> <INCHI_KEY>
GTMKBVNAJMQYKF-UHFFFAOYSA-N

> <FORMULA>
C7H12N2O5S

> <MOLECULAR_WEIGHT>
236.24

> <EXACT_MASS>
236.046692668

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.213716818689885

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-acetamido-3-methyl-3-(nitrosulfanyl)butanoic acid

> <ALOGPS_LOGP>
0.81

> <JCHEM_LOGP>
0.03218726999999989

> <ALOGPS_LOGS>
-2.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.86654380690797

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3100002105613893

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6633436733662261

> <JCHEM_POLAR_SURFACE_AREA>
109.54000000000002

> <JCHEM_REFRACTIVITY>
52.67490000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-acetamido-3-methyl-3-(nitrosulfanyl)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-21         0                                  
HETATM    1  C   UNK     0       4.322  -0.224   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.963  -2.813   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.885  -0.964   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       7.953  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.526  -3.553   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.593  -4.663   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       6.031  -3.923   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.448  -1.704   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.818  -3.198   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.078  -0.209   0.000  0.00  0.00           C+0
HETATM   12  S   UNK     0      10.943  -1.334   0.000  0.00  0.00           S+0
HETATM   13  N   UNK     0      12.010  -2.443   0.000  0.00  0.00           N+1
HETATM   14  O   UNK     0      13.505  -2.073   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      11.583  -3.923   0.000  0.00  0.00           O-1
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0244752
HETATM    1  C1  UNL     1       3.457  -0.900   1.084  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.365  -0.728   0.091  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.504  -1.364  -0.986  1.00  0.00           O  
HETATM    4  N1  UNL     1       1.245   0.097   0.340  1.00  0.00           N  
HETATM    5  C3  UNL     1       0.180   0.263  -0.646  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.048   1.659  -1.044  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.513   2.652  -0.399  1.00  0.00           O  
HETATM    8  O3  UNL     1      -0.627   2.027  -2.228  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.068  -0.431  -0.171  1.00  0.00           C  
HETATM   10  C6  UNL     1      -1.532   0.102   1.174  1.00  0.00           C  
HETATM   11  C7  UNL     1      -0.741  -1.891   0.018  1.00  0.00           C  
HETATM   12  S1  UNL     1      -2.422  -0.253  -1.320  1.00  0.00           S  
HETATM   13  N2  UNL     1      -3.045   1.372  -1.327  1.00  0.00           N1+
HETATM   14  O4  UNL     1      -3.617   1.808  -2.335  1.00  0.00           O  
HETATM   15  O5  UNL     1      -2.916   2.171  -0.222  1.00  0.00           O1-
HETATM   16  H1  UNL     1       3.720  -1.970   1.094  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.217  -0.487   2.085  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.352  -0.378   0.676  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.159   0.598   1.231  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.498  -0.333  -1.554  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.123   2.380  -3.035  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.609  -0.172   1.246  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.446   1.172   1.306  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.001  -0.494   1.965  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.074  -2.304  -0.773  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.345  -2.111   1.039  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.694  -2.486  -0.057  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5   19
CONECT    5    6    9   20
CONECT    6    7    7    8
CONECT    8   21
CONECT    9   10   11   12
CONECT   10   22   23   24
CONECT   11   25   26   27
CONECT   12   13
CONECT   13   14   14   15
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Acetyl-3-(nitrosulphanyl)-L-valine	Generator

Chemical Formula

C₇H₁₂N₂O₅S

Average Molecular Weight

236.24

Monoisotopic Molecular Weight

236.046692668

IUPAC Name

2-acetamido-3-methyl-3-(nitrosulfanyl)butanoic acid

Traditional Name

2-acetamido-3-methyl-3-(nitrosulfanyl)butanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)NC(C(O)=O)C(C)(C)S[N+]([O-])=O

InChI Identifier

InChI=1S/C7H12N2O5S/c1-4(10)8-5(6(11)12)7(2,3)15-9(13)14/h5H,1-3H3,(H,8,10)(H,11,12)

InChI Key

GTMKBVNAJMQYKF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

Valine or derivatives
N-acyl-alpha-amino acid
Methyl-branched fatty acid
Thia fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Acetamide
Organic nitro compound
Secondary carboxylic acid amide
Carboxamide group
Organic 1,3-dipolar compound
Allyl-type 1,3-dipolar organic compound
Sulfenyl compound
Monocarboxylic acid or derivatives
Carboxylic acid
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic zwitterion
Organosulfur compound
Organooxygen compound
Organonitrogen 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)

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	0.81	ALOGPS
logP	0.032	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.54 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	52.67 m³·mol⁻¹	ChemAxon
Polarizability	21.21 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]+	139.144	30932474
DeepCCS	[M-H]-	135.809	30932474
DeepCCS	[M-2H]-	171.577	30932474
DeepCCS	[M+Na]+	147.709	30932474
AllCCS	[M+H]+	147.0	32859911
AllCCS	[M+H-H2O]+	143.8	32859911
AllCCS	[M+NH4]+	150.0	32859911
AllCCS	[M+Na]+	150.9	32859911
AllCCS	[M-H]-	147.8	32859911
AllCCS	[M+Na-2H]-	148.9	32859911
AllCCS	[M+HCOO]-	150.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-3-(nitrosulfanyl)-L-valine	CC(=O)NC(C(O)=O)C(C)(C)S[N+]([O-])=O	2866.8	Standard polar	33892256
N-Acetyl-3-(nitrosulfanyl)-L-valine	CC(=O)NC(C(O)=O)C(C)(C)S[N+]([O-])=O	1672.6	Standard non polar	33892256
N-Acetyl-3-(nitrosulfanyl)-L-valine	CC(=O)NC(C(O)=O)C(C)(C)S[N+]([O-])=O	1824.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Acetyl-3-(nitrosulfanyl)-L-valine,2TMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)(C)S[N+](=O)[O-])[Si](C)(C)C	1827.2	Semi standard non polar	33892256
N-Acetyl-3-(nitrosulfanyl)-L-valine,2TMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)(C)S[N+](=O)[O-])[Si](C)(C)C	1844.4	Standard non polar	33892256
N-Acetyl-3-(nitrosulfanyl)-L-valine,2TMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)(C)S[N+](=O)[O-])[Si](C)(C)C	2164.8	Standard polar	33892256
N-Acetyl-3-(nitrosulfanyl)-L-valine,2TBDMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[N+](=O)[O-])[Si](C)(C)C(C)(C)C	2309.4	Semi standard non polar	33892256
N-Acetyl-3-(nitrosulfanyl)-L-valine,2TBDMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[N+](=O)[O-])[Si](C)(C)C(C)(C)C	2276.7	Standard non polar	33892256
N-Acetyl-3-(nitrosulfanyl)-L-valine,2TBDMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[N+](=O)[O-])[Si](C)(C)C(C)(C)C	2400.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-(nitrosulfanyl)-L-valine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9800000000-e5ccd8b544c3d61202b9	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-(nitrosulfanyl)-L-valine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-(nitrosulfanyl)-L-valine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-(nitrosulfanyl)-L-valine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-(nitrosulfanyl)-L-valine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetyl-3-(nitrosulfanyl)-L-valine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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

10629308

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21882149

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 N-Acetyl-3-(nitrosulfanyl)-L-valine (HMDB0244752)

MOL for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

3D MOL for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

3D SDF for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

3D-SDF for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

PDB for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

3D PDB for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

SMILES for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

INCHI for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

Structure for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

3D Structure for HMDB0244752 (N-Acetyl-3-(nitrosulfanyl)-L-valine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra