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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-08-28 06:31:47 UTC

Update Date

2022-09-22 18:34:34 UTC

HMDB ID

HMDB0242184

Secondary Accession Numbers

None

Metabolite Identification

Common Name

N-Acetylalliin

Description

N-Acetylalliin 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 N-Acetylalliin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652308282101082D          

 15 14  0  0  1  0            999 V2000
   -1.6500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 S   0  0  1  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  3  1  0  0  0  0
  6  2  1  4  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  7  9  1  1  0  0  0
 10  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 14  4  1  1  0  0  0
 14  5  1  0  0  0  0
 14 13  2  0  0  0  0
  7 15  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0242184

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@](C[S@@](=O)CC=C)(N=C(C)O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H13NO4S/c1-3-4-14(13)5-7(8(11)12)9-6(2)10/h3,7H,1,4-5H2,2H3,(H,9,10)(H,11,12)/t7-,14-/m0/s1

> <INCHI_KEY>
CCCNUHFRBBIFHO-WJWGPLDTSA-N

> <FORMULA>
C8H13NO4S

> <MOLECULAR_WEIGHT>
219.26

> <EXACT_MASS>
219.056529077

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.145412377283762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-[(S)-prop-2-ene-1-sulfinyl]propanoic acid

> <JCHEM_LOGP>
-0.8408308713333336

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.750186673344209

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5453989598068314

> <JCHEM_PKA_STRONGEST_BASIC>
0.8223288054011423

> <JCHEM_POLAR_SURFACE_AREA>
86.96000000000001

> <JCHEM_REFRACTIVITY>
53.6881

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-2-[(1-hydroxyethylidene)amino]-3-[(S)-prop-2-ene-1-sulfinyl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-AUG-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-AUG-21         0                                  
HETATM    1  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.390   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       3.850   4.001   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       6.160   2.667   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       5.390   1.334   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       3.080   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.540   0.000   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       0.770   1.334   0.000  0.00  0.00           S+0
HETATM   15  H   UNK     0       2.310   1.334   0.000  0.00  0.00           H+0
CONECT    1    3                                                            
CONECT    2    6                                                            
CONECT    3    1    4                                                       
CONECT    4    3   14                                                       
CONECT    5    7   14                                                       
CONECT    6    2    9   10                                                  
CONECT    7    5    8    9   15                                             
CONECT    8    7   11   12                                                  
CONECT    9    6    7                                                       
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13   14                                                            
CONECT   14    4    5   13                                                  
CONECT   15    7                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

COMPND    HMDB0242184
HETATM    1  C1  UNL     1       3.370   1.837  -0.411  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.193   0.741   0.297  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.088  -0.238  -0.020  1.00  0.00           C  
HETATM    4  S1  UNL     1       0.979  -0.377   1.450  1.00  0.00           S  
HETATM    5  O1  UNL     1       1.854  -1.245   2.397  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.285  -1.572   0.924  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.067  -1.130  -0.261  1.00  0.00           C  
HETATM    8  N1  UNL     1      -1.823   0.040  -0.159  1.00  0.00           N  
HETATM    9  C6  UNL     1      -1.635   1.244   0.039  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.769   2.241   0.080  1.00  0.00           C  
HETATM   11  O2  UNL     1      -0.385   1.785   0.239  1.00  0.00           O  
HETATM   12  C8  UNL     1      -1.960  -2.274  -0.620  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.179  -2.069  -0.773  1.00  0.00           O  
HETATM   14  O4  UNL     1      -1.431  -3.561  -0.780  1.00  0.00           O  
HETATM   15  H1  UNL     1       2.682   2.020  -1.249  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.166   2.508  -0.155  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.854   0.528   1.133  1.00  0.00           H  
HETATM   18  H4  UNL     1       1.521   0.161  -0.856  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.582  -1.196  -0.208  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.229  -2.533   0.636  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.928  -1.837   1.791  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.350  -1.026  -1.118  1.00  0.00           H  
HETATM   23  H9  UNL     1      -2.425   3.245  -0.244  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.566   1.946  -0.631  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.136   2.351   1.124  1.00  0.00           H  
HETATM   26  H12 UNL     1      -0.199   2.359   1.043  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.378  -3.947  -1.720  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5    5    6
CONECT    6    7   20   21
CONECT    7    8   12   22
CONECT    8    9    9
CONECT    9   10   11
CONECT   10   23   24   25
CONECT   11   26
CONECT   12   13   13   14
CONECT   14   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₈H₁₃NO₄S

Average Molecular Weight

219.26

Monoisotopic Molecular Weight

219.056529077

IUPAC Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-[(S)-prop-2-ene-1-sulfinyl]propanoic acid

Traditional Name

(2R)-2-[(1-hydroxyethylidene)amino]-3-[(S)-prop-2-ene-1-sulfinyl]propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](C[S@@](=O)CC=C)(N=C(C)O)C(O)=O

InChI Identifier

InChI=1S/C8H13NO4S/c1-3-4-14(13)5-7(8(11)12)9-6(2)10/h3,7H,1,4-5H2,2H3,(H,9,10)(H,11,12)/t7-,14-/m0/s1

InChI Key

CCCNUHFRBBIFHO-WJWGPLDTSA-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
Sulfoxide
Allyl sulfur compound
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Sulfinyl compound
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	ChemAxon
pKa (Strongest Acidic)	3.55	ChemAxon
pKa (Strongest Basic)	0.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.96 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	53.69 m³·mol⁻¹	ChemAxon
Polarizability	21.15 Å³	ChemAxon
Number of Rings	0	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]+	147.788	30932474
DeepCCS	[M-H]-	145.392	30932474
DeepCCS	[M-2H]-	178.667	30932474
DeepCCS	[M+Na]+	153.7	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Acetylalliin	[H][C@@](C[S@@](=O)CC=C)(N=C(C)O)C(O)=O	3006.0	Standard polar	33892256
N-Acetylalliin	[H][C@@](C[S@@](=O)CC=C)(N=C(C)O)C(O)=O	1655.1	Standard non polar	33892256
N-Acetylalliin	[H][C@@](C[S@@](=O)CC=C)(N=C(C)O)C(O)=O	1759.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylalliin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9100000000-86380a4b6629022a37b4	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Acetylalliin 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 - N-Acetylalliin 10V, Positive-QTOF	splash10-00e9-3590000000-d4a94da3b482180a1315	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylalliin 20V, Positive-QTOF	splash10-001u-9100000000-1f6518e9fdeec80a9499	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylalliin 40V, Positive-QTOF	splash10-00dj-9000000000-172405f1c94a6d8529ab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylalliin 10V, Negative-QTOF	splash10-0040-8900000000-454fda9934db5ee0770e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylalliin 20V, Negative-QTOF	splash10-001r-9500000000-e354fde5358b2c21feb1	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Acetylalliin 40V, Negative-QTOF	splash10-0002-9000000000-97669262005892764709	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
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

58170394

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122164824

PDB ID

Not Available

ChEBI ID

133430

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

Kong SW, Hernandez-Ferrer C: Assessment of coverage for endogenous metabolites and exogenous chemical compounds using an untargeted metabolomics platform. Pac Symp Biocomput. 2020;25:587-598. [PubMed:31797630 ]

Showing metabocard for N-Acetylalliin (HMDB0242184)

MOL for HMDB0242184 (N-Acetylalliin)

3D MOL for HMDB0242184 (N-Acetylalliin)

3D SDF for HMDB0242184 (N-Acetylalliin)

3D-SDF for HMDB0242184 (N-Acetylalliin)

PDB for HMDB0242184 (N-Acetylalliin)

3D PDB for HMDB0242184 (N-Acetylalliin)

SMILES for HMDB0242184 (N-Acetylalliin)

INCHI for HMDB0242184 (N-Acetylalliin)

Structure for HMDB0242184 (N-Acetylalliin)

3D Structure for HMDB0242184 (N-Acetylalliin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra