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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 07:01:30 UTC

Update Date

2021-09-26 23:01:15 UTC

HMDB ID

HMDB0250051

Secondary Accession Numbers

None

Metabolite Identification

Common Name

s-Nitroso-n-acetyl-d-penicillamine

Description

s-Nitroso-n-acetyl-d-penicillamine, also known as N-acetyl-S-nitrosopenicillamine or S-NONAP, 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 a significant number of articles have been published on s-Nitroso-n-acetyl-d-penicillamine. This compound has been identified in human blood as reported by (PMID: 31557052 ). S-nitroso-n-acetyl-d-penicillamine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically s-Nitroso-n-acetyl-d-penicillamine 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

  Mrv1652309112109012D          

 14 13  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  0  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
  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
M  END
> <DATABASE_ID>
HMDB0250051

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)NC(C(O)=O)C(C)(C)SN=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)

> <INCHI_KEY>
ZIIQCSMRQKCOCT-UHFFFAOYSA-N

> <FORMULA>
C7H12N2O4S

> <MOLECULAR_WEIGHT>
220.24

> <EXACT_MASS>
220.051778048

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.484207009587113

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.05

> <JCHEM_LOGP>
0.39634805799999995

> <ALOGPS_LOGS>
-1.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.003352605753818

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3565568591608903

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4926205222270887

> <JCHEM_POLAR_SURFACE_AREA>
95.83000000000001

> <JCHEM_REFRACTIVITY>
51.927800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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       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+0
HETATM   14  O   UNK     0      13.505  -2.073   0.000  0.00  0.00           O+0
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                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-[(1-Hydroxyethylidene)amino]-3-methyl-3-(nitrososulfanyl)butanoate	HMDB
2-[(1-Hydroxyethylidene)amino]-3-methyl-3-(nitrososulphanyl)butanoate	HMDB
2-[(1-Hydroxyethylidene)amino]-3-methyl-3-(nitrososulphanyl)butanoic acid	HMDB
N-Acetyl-S-nitrosopenicillamine	HMDB
N2-Acetyl-S-nitroso-D,L-penicillinaminamide	HMDB
S-NONAP	HMDB
S-Nitroso-N-acetylpenicillamine	HMDB
S-Nitrosylacetylpenicillamine	HMDB
SNAP (no donor)	HMDB

Chemical Formula

C₇H₁₂N₂O₄S

Average Molecular Weight

220.24

Monoisotopic Molecular Weight

220.051778048

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)NC(C(O)=O)C(C)(C)SN=O

InChI Identifier

InChI=1S/C7H12N2O4S/c1-4(10)8-5(6(11)12)7(2,3)14-9-13/h5H,1-3H3,(H,8,10)(H,11,12)

InChI Key

ZIIQCSMRQKCOCT-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

N-acyl-alpha-amino acid
Valine or derivatives
Branched fatty acid
Thia fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Acetamide
Carboxamide group
Organic s-nitroso compound
Nitrosothiol
Nitrosothiol-group
Secondary carboxylic acid amide
Carboxylic acid
Monocarboxylic acid or derivatives
Organic nitroso compound
Sulfenyl compound
Organonitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organosulfur compound
Organic oxide
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	1.05	ALOGPS
logP	0.4	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.36	ChemAxon
pKa (Strongest Basic)	-1.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	95.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	51.93 m³·mol⁻¹	ChemAxon
Polarizability	20.48 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]+	142.746	30932474
DeepCCS	[M-H]-	140.135	30932474
DeepCCS	[M-2H]-	175.694	30932474
DeepCCS	[M+Na]+	150.659	30932474
AllCCS	[M+H]+	144.4	32859911
AllCCS	[M+H-H2O]+	141.1	32859911
AllCCS	[M+NH4]+	147.5	32859911
AllCCS	[M+Na]+	148.4	32859911
AllCCS	[M-H]-	145.5	32859911
AllCCS	[M+Na-2H]-	146.7	32859911
AllCCS	[M+HCOO]-	148.2	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
s-Nitroso-n-acetyl-d-penicillamine,1TMS,isomer #1	CC(=O)NC(C(=O)O[Si](C)(C)C)C(C)(C)SN=O	1746.2	Semi standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TMS,isomer #1	CC(=O)NC(C(=O)O[Si](C)(C)C)C(C)(C)SN=O	1657.3	Standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TMS,isomer #1	CC(=O)NC(C(=O)O[Si](C)(C)C)C(C)(C)SN=O	2640.4	Standard polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TMS,isomer #2	CC(=O)N(C(C(=O)O)C(C)(C)SN=O)[Si](C)(C)C	1712.6	Semi standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TMS,isomer #2	CC(=O)N(C(C(=O)O)C(C)(C)SN=O)[Si](C)(C)C	1686.9	Standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TMS,isomer #2	CC(=O)N(C(C(=O)O)C(C)(C)SN=O)[Si](C)(C)C	2598.6	Standard polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,2TMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)(C)SN=O)[Si](C)(C)C	1732.9	Semi standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,2TMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)(C)SN=O)[Si](C)(C)C	1774.1	Standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,2TMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C)C(C)(C)SN=O)[Si](C)(C)C	2187.7	Standard polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TBDMS,isomer #1	CC(=O)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)SN=O	1960.1	Semi standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TBDMS,isomer #1	CC(=O)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)SN=O	1881.8	Standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TBDMS,isomer #1	CC(=O)NC(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)SN=O	2674.6	Standard polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TBDMS,isomer #2	CC(=O)N(C(C(=O)O)C(C)(C)SN=O)[Si](C)(C)C(C)(C)C	1969.9	Semi standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TBDMS,isomer #2	CC(=O)N(C(C(=O)O)C(C)(C)SN=O)[Si](C)(C)C(C)(C)C	1897.5	Standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,1TBDMS,isomer #2	CC(=O)N(C(C(=O)O)C(C)(C)SN=O)[Si](C)(C)C(C)(C)C	2626.5	Standard polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,2TBDMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)SN=O)[Si](C)(C)C(C)(C)C	2213.7	Semi standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,2TBDMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)SN=O)[Si](C)(C)C(C)(C)C	2199.6	Standard non polar	33892256
s-Nitroso-n-acetyl-d-penicillamine,2TBDMS,isomer #1	CC(=O)N(C(C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)SN=O)[Si](C)(C)C(C)(C)C	2410.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-9800000000-06a5118ea35763ff5d0b	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine 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 - s-Nitroso-n-acetyl-d-penicillamine 10V, Positive-QTOF	splash10-0bt9-0940000000-1e7939ae09ad8d852793	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine 20V, Positive-QTOF	splash10-0irc-1920000000-7abface95714bb6576ae	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine 40V, Positive-QTOF	splash10-03di-7900000000-a42f914fc3372ac413c4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine 10V, Negative-QTOF	splash10-08fr-9800000000-353972dc33c15d20aa2d	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine 20V, Negative-QTOF	splash10-03di-9000000000-f3c8ce3d49e45ba7a804	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - s-Nitroso-n-acetyl-d-penicillamine 40V, Negative-QTOF	splash10-03di-9000000000-f3c8ce3d49e45ba7a804	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

5041

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5231

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 s-Nitroso-n-acetyl-d-penicillamine (HMDB0250051)

MOL for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

3D MOL for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

3D SDF for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

3D-SDF for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

PDB for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

3D PDB for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

SMILES for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

INCHI for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

Structure for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

3D Structure for HMDB0250051 (s-Nitroso-n-acetyl-d-penicillamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra