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Showing NP-Card for (2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid (NP0253704)

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Record Information
Version2.0
Created at2022-09-07 17:39:10 UTC
Updated at2022-09-07 17:39:11 UTC
NP-MRD IDNP0253704
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid
DescriptionEntadamide C belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. (2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid is found in Clinacanthus siamensis and Entada phaseoloides. (2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid was first documented in 2003 (PMID: 14646322). Based on a literature review very few articles have been published on Entadamide C (PMID: 31626839).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)


  Mrv1652309072219392D          

 11 10  0  0  0  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  5  0  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
    1.2375    0.7145    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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   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
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
Download

3D MOL for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)

     RDKit          3D

 22 21  0  0  0  0  0  0  0  0999 V2000
    4.4032   -0.6388    0.2124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8942   -0.8260   -0.7265 S   0  0  0  0  0  3  0  0  0  0  0  0
    2.2218   -2.3377   -0.3517 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.7682    0.3760   -0.1127 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4598    0.2708   -0.2682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4641    1.2891    0.2539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0038    2.4026    0.9319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7339    1.1707    0.0936 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2863    0.0439   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7775    0.0238   -0.3281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344   -1.0755   -0.9995 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1100   -0.3628    1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9618   -1.5943    0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9647    0.1782   -0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1229    1.2611    0.4249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046   -0.5986   -0.7967 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5596    2.2358    1.7633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -0.9251   -0.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1500    0.2133   -1.6991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199   -0.1636    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2456    0.9511   -0.6789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8191   -1.8941   -0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  1
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  9 18  1  0
  9 19  1  0
 10 20  1  0
 10 21  1  0
 11 22  1  0
M  CHG  2   2   1   3  -1
M  END
Download

3D SDF for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)


  Mrv1652309072219392D          

 11 10  0  0  0  0            999 V2000
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 S   0  3  0  0  0  0  0  0  0  0  0  0
    2.0625    2.1434    0.0000 O   0  5  0  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
    1.2375    0.7145    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
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   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
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
  8  9  1  4  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  CHG  2   2   1   3  -1
M  END
> <DATABASE_ID>
NP0253704

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[S+]([O-])\C=C\C(O)=NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO3S/c1-11(10)5-2-6(9)7-3-4-8/h2,5,8H,3-4H2,1H3,(H,7,9)/b5-2+

> <INCHI_KEY>
LBGAGBWSXXFWGZ-GORDUTHDSA-N

> <FORMULA>
C6H11NO3S

> <MOLECULAR_WEIGHT>
177.22

> <EXACT_MASS>
177.045964392

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
17.897936317991793

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid

> <JCHEM_LOGP>
-2.002567442630555

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.572722185880579

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.661005240860634

> <JCHEM_PKA_STRONGEST_BASIC>
3.78301880183979

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
45.2761

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)

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PDB for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0       4.620   2.667   0.000  0.00  0.00           S+1
HETATM    3  O   UNK     0       3.850   4.001   0.000  0.00  0.00           O-1
HETATM    4  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -3.080  -2.667   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                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)
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SMILES for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)
C[S+]([O-])\C=C\C(O)=NCCO
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INCHI for NP0253704 ((2e)-n-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid)
InChI=1S/C6H11NO3S/c1-11(10)5-2-6(9)7-3-4-8/h2,5,8H,3-4H2,1H3,(H,7,9)/b5-2+
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View in JSmol
SynonymsNot Available
Chemical FormulaC6H11NO3S
Average Mass177.2200 Da
Monoisotopic Mass177.04596 Da
IUPAC Name(2E)-N-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid
Traditional Name(2E)-N-(2-hydroxyethyl)-3-methanesulfinylprop-2-enimidic acid
CAS Registry NumberNot Available
SMILES
C[S+]([O-])\C=C\C(O)=NCCO
InChI Identifier
InChI=1S/C6H11NO3S/c1-11(10)5-2-6(9)7-3-4-8/h2,5,8H,3-4H2,1H3,(H,7,9)/b5-2+
InChI KeyLBGAGBWSXXFWGZ-GORDUTHDSA-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
Clinacanthus siamensisLOTUS Database
Entada phaseoloidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassAmines  
Direct ParentN-acylethanolamines  
Alternative Parents
Substituents
  • N-acylethanolamine
    • 

  • Acrylic acid or derivatives
    • 

  • Carboxamide group
    • 

  • Sulfoxide
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Sulfinyl compound
    • 

  • Alcohol
    • 

  • Primary alcohol
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen 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-2ChemAxon
pKa (Strongest Acidic)5.66ChemAxon
pKa (Strongest Basic)3.78ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area69.89 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity45.28 m³·mol⁻¹ChemAxon
Polarizability17.9 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 IDC00031764  
Chemspider ID8416833  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10241346  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Mutazah R, Hamid HA, Mazila Ramli AN, Fasihi Mohd Aluwi MF, Yusoff MM: In vitro cytotoxicity of Clinacanthus nutans fractions on breast cancer cells and molecular docking study of sulphur containing compounds against caspase-3. Food Chem Toxicol. 2020 Jan;135:110869. doi: 10.1016/j.fct.2019.110869. Epub 2019  Oct 15. [PubMed:31626839  ] 
  2. Tuntiwachwuttikul P, Pootaeng-on Y, Pansa P, Srisanpang T, Taylor WC: Sulfur-containing compounds from Clinacanthus siamensis. Chem Pharm Bull (Tokyo). 2003 Dec;51(12):1423-5. doi: 10.1248/cpb.51.1423. [PubMed:14646322  ] 
  3. LOTUS database [Link]