Np mrd loader

Showing NP-Card for (2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid (NP0162075)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-02 20:24:36 UTC
Updated at2022-09-02 20:24:37 UTC
NP-MRD IDNP0162075
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid
DescriptionAlliin, also known as isoalliin or PCSO, belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom. (2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid is found in Allium cepa, Allium chinense, Allium sativum and Allium ursinum. (2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid was first documented in 2022 (PMID: 36014767). Based on a literature review a small amount of articles have been published on Alliin (PMID: 36013310) (PMID: 35932686) (PMID: 35841679) (PMID: 35806016).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)


  Mrv1652309022222242D          

 11 10  0  0  1  0            999 V2000
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  CHG  2   4   1   5  -1
M  END
Download

3D MOL for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    4.0993    0.5161   -0.2666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145    0.9458    0.1800 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7614    0.0018    0.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689    0.6305   -0.7597 S   0  0  0  0  0  3  0  0  0  0  0  0
    0.0488    2.1801   -0.2803 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.9563   -0.3986   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5240   -0.4456    0.6805 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9054    0.8712    1.1431 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6695   -1.3987    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4405   -2.5763    0.3697 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073   -1.0110    1.2087 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8996    1.2251   -0.3264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2201   -0.5255   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7467    1.9569    0.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4345    0.0010    1.3396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0924   -0.9997   -0.0344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7185    0.0527   -1.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7611   -1.4128   -1.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7576   -0.8356    1.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0631    1.3036    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418    1.4070    0.3220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7411   -1.4881    0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  1  1
  4  3  1  0
  3  2  1  0
  2  1  2  3
  7  9  1  0
  9 11  1  0
  9 10  2  0
  8 20  1  0
  8 21  1  0
  7 19  1  1
  6 17  1  0
  6 18  1  0
  3 15  1  0
  3 16  1  0
  2 14  1  0
  1 12  1  0
  1 13  1  0
 11 22  1  0
M  CHG  2   4   1   5  -1
M  END
Download

3D SDF for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)


  Mrv1652309022222242D          

 11 10  0  0  1  0            999 V2000
    1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    3.1895    2.6664    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6184    2.6664    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    0.6039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
M  CHG  2   4   1   5  -1
M  END
> <DATABASE_ID>
NP0162075

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11?/m1/s1

> <INCHI_KEY>
XUHLIQGRKRUKPH-ITDPFOOWSA-N

> <FORMULA>
C6H11NO3S

> <MOLECULAR_WEIGHT>
177.22

> <EXACT_MASS>
177.045964392

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.073987774877413

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-2.14

> <JCHEM_LOGP>
-3.7406126292045894

> <ALOGPS_LOGS>
-0.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.14468590059375

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.837251426076854

> <JCHEM_PKA_STRONGEST_BASIC>
8.447951464574974

> <JCHEM_POLAR_SURFACE_AREA>
80.39

> <JCHEM_REFRACTIVITY>
43.7226

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.85e+01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)

Download
PDB for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)
HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       1.953   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0       5.954   3.437   0.000  0.00  0.00           S+1
HETATM    5  O   UNK     0       5.954   4.977   0.000  0.00  0.00           O-1
HETATM    6  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       8.621   4.977   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.955   1.127   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

Download
3D PDB for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)
Download
SMILES for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)
N[C@H](C[S+]([O-])CC=C)C(O)=O
Download
INCHI for NP0162075 ((2s)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid)
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11?/m1/s1
Download
View in JSmol
Synonyms
ValueSource
S-Allylcysteine sulfoxideMeSH
Alliin, (L-ala)-(S)-isomerMeSH
IsoalliinMeSH
PCSOMeSH
Alliin, (L-ala)-isomerMeSH
Alliin, (L-ala)-(R)-isomerMeSH
S-(2-Propenyl)cysteine sulfoxideMeSH
Chemical FormulaC6H11NO3S
Average Mass177.2200 Da
Monoisotopic Mass177.04596 Da
IUPAC Name(2S)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid
Traditional Name(2S)-2-amino-3-(prop-2-ene-1-sulfinyl)propanoic acid
CAS Registry NumberNot Available
SMILES
N[C@H](C[S+]([O-])CC=C)C(O)=O
InChI Identifier
InChI=1S/C6H11NO3S/c1-2-3-11(10)4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-,11?/m1/s1
InChI KeyXUHLIQGRKRUKPH-ITDPFOOWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium cepaLOTUS Database
Allium chinenseLOTUS Database
Allium sativumLOTUS Database
Allium ursinumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentD-alpha-amino acids  
Alternative Parents
Substituents
  • D-alpha-amino acid
    • 

  • Sulfoxide
    • 

  • Allyl sulfur compound
    • 

  • Amino acid
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Sulfinyl compound
    • 

  • Amine
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Primary amine
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Primary aliphatic amine
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-3.7ChemAxon
logS-0.66ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity43.72 m³·mol⁻¹ChemAxon
Polarizability17.07 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001336  
Chemspider ID28296246  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlliin  
METLIN IDNot Available
PubChem Compound15558642  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Livingstone TL, Saha S, Bernuzzi F, Savva GM, Troncoso-Rey P, Traka MH, Mills RD, Ball RY, Mithen RF: Accumulation of Sulforaphane and Alliin in Human Prostate Tissue. Nutrients. 2022 Aug 10;14(16):3263. doi: 10.3390/nu14163263. [PubMed:36014767  ] 
  2. Lestari AR, Batubara I, Wahyudi ST, Ilmiawati A, Achmadi SS: Bioactive Compounds in Garlic (Allium sativum) and Black Garlic as Antigout Agents, Using Computer Simulation. Life (Basel). 2022 Jul 27;12(8):1131. doi: 10.3390/life12081131. [PubMed:36013310  ] 
  3. Mengers HG, Schier C, Zimmermann M, C H Gruhlke M, Block E, Blank LM, Slusarenko AJ: Seeing the smell of garlic: Detection of gas phase volatiles from crushed garlic (Allium sativum), onion (Allium cepa), ramsons (Allium ursinum) and human garlic breath using SESI-Orbitrap MS. Food Chem. 2022 Dec 15;397:133804. doi: 10.1016/j.foodchem.2022.133804. Epub 2022  Jul 28. [PubMed:35932686  ] 
  4. Li J, Dadmohammadi Y, Li P, Madarshahian S, Abbaspourrad A: Generation of garlic flavor after frying by infusing alliin into potato strips using pulsed electric field and assisted infusion methods. Food Chem. 2022 Dec 1;396:133643. doi: 10.1016/j.foodchem.2022.133643. Epub 2022  Jul 8. [PubMed:35841679  ] 
  5. Xia SW, Hang LF, Ali S, Xu XY, Liu YJ, Yan QQ, Luo QY, Li Y, Lin LJ, Li HX, Zhang XA, Huang LK, Ma X, Lai YS: Biosynthesis and Metabolism of Garlic Odor Compounds in Cultivated Chinese Chives (Allium tuberosum) and Wild Chinese Chives (Allium hookeri). Int J Mol Sci. 2022 Jun 24;23(13):7013. doi: 10.3390/ijms23137013. [PubMed:35806016  ] 
  6. LOTUS database [Link]