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Showing NP-Card for (2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid (NP0286643)

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Record Information
Version1.0
Created at2022-09-09 15:18:19 UTC
Updated at2022-09-09 15:18:19 UTC
NP-MRD IDNP0286643
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid
DescriptionPenangin belongs to the class of organic compounds known as vinylogous thioesters. These are organic compounds containing a thioester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. (2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid is found in Glycosmis chlorosperma, Glycosmis mauritiana and Glycosmis parviflora. It was first documented in 2010 (PMID: 20701297). Based on a literature review a significant number of articles have been published on penangin (PMID: 36113990) (PMID: 36113989) (PMID: 36113988) (PMID: 36113987).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)


  Mrv1652309092217182D          

  8  7  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   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    1.4289    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)

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3D SDF for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)

  Mrv1652309092217182D          

  8  7  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 N   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    1.4289    0.0000 O   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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286643

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS\C=C\C(O)=NC

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NOS/c1-6-5(7)3-4-8-2/h3-4H,1-2H3,(H,6,7)/b4-3+

> <INCHI_KEY>
VRYCXSSOSLPIDH-ONEGZZNKSA-N

> <FORMULA>
C5H9NOS

> <MOLECULAR_WEIGHT>
131.19

> <EXACT_MASS>
131.040485088

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
14.041445166925143

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-methyl-3-(methylsulfanyl)prop-2-enimidic acid

> <JCHEM_LOGP>
0.036418575899198745

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.194494365492447

> <JCHEM_PKA_STRONGEST_BASIC>
7.305615603496223

> <JCHEM_POLAR_SURFACE_AREA>
32.59

> <JCHEM_REFRACTIVITY>
37.3811

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-methyl-3-(methylsulfanyl)prop-2-enimidic acid

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)
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PDB for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)
HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.850   1.334   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      -0.770  -1.334   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   14    0
END

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3D PDB for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)
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SMILES for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)
CS\C=C\C(O)=NC
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INCHI for NP0286643 ((2e)-n-methyl-3-(methylsulfanyl)prop-2-enimidic acid)
InChI=1S/C5H9NOS/c1-6-5(7)3-4-8-2/h3-4H,1-2H3,(H,6,7)/b4-3+
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SynonymsNot Available
Chemical FormulaC5H9NOS
Average Mass131.1900 Da
Monoisotopic Mass131.04049 Da
IUPAC Name(2E)-N-methyl-3-(methylsulfanyl)prop-2-enimidic acid
Traditional Name(2E)-N-methyl-3-(methylsulfanyl)prop-2-enimidic acid
CAS Registry NumberNot Available
SMILES
CS\C=C\C(O)=NC
InChI Identifier
InChI=1S/C5H9NOS/c1-6-5(7)3-4-8-2/h3-4H,1-2H3,(H,6,7)/b4-3+
InChI KeyVRYCXSSOSLPIDH-ONEGZZNKSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Glycosmis chlorospermaLOTUS Database
Glycosmis mauritianaLOTUS Database
Glycosmis parvifloraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vinylogous thioesters. These are organic compounds containing a thioester group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassVinylogous thioesters  
Sub ClassNot Available
Direct ParentVinylogous thioesters  
Alternative Parents
Substituents
  • Vinylogous thioester
    • 

  • Acrylic acid or derivatives
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Thioenolether
    • 

  • Carboxylic acid derivative
    • 

  • Sulfenyl compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • 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
logP0.036ChemAxon
pKa (Strongest Acidic)5.19ChemAxon
pKa (Strongest Basic)7.31ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.59 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.38 m³·mol⁻¹ChemAxon
Polarizability14.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8594647  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10419217  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Concha-Miranda M, Tang W, Hartmann K, Brecht M: Large-scale mapping of vocalization-related activity in the functionally diverse nuclei in rat posterior brainstem. J Neurosci. 2022 Sep 16. pii: JNEUROSCI.0813-22.2022. doi: 10.1523/JNEUROSCI.0813-22.2022. [PubMed:36113990  ] 
  2. Kausto J, Gluschkoff K, Turunen J, Selinheimo S, Peutere L, Vaananen A: Psychotherapy and change in mental health-related work disability: a prospective Finnish population-level register-based study with a quasi-experimental design. J Epidemiol Community Health. 2022 Sep 16. pii: jech-2022-218941. doi: 10.1136/jech-2022-218941. [PubMed:36113989  ] 
  3. Meulemans L, Baert Desurmont S, Waill MC, Castelain G, Killian A, Hauchard J, Frebourg T, Coulet F, Martins A, Muleris M, Gaildrat P: Comprehensive RNA and protein functional assessments contribute to the clinical interpretation of MSH2 variants causing in-frame splicing alterations. J Med Genet. 2022 Sep 16. pii: jmg-2022-108576. doi: 10.1136/jmg-2022-108576. [PubMed:36113988  ] 
  4. Otsuji S, Nishio Y, Tsujita M, Rio M, Huber C, Anton-Plagaro C, Mizuno S, Kawano Y, Miyatake S, Simon M, van Binsbergen E, van Jaarsveld RH, Matsumoto N, Cormier-Daire V, J Cullen P, Saitoh S, Kato K: Clinical diversity and molecular mechanism of VPS35L-associated Ritscher-Schinzel syndrome. J Med Genet. 2022 Sep 16. pii: jmg-2022-108602. doi: 10.1136/jmg-2022-108602. [PubMed:36113987  ] 
  5. Pacher T, Raninger A, Lorbeer E, Brecker L, But PP, Greger H: Alcoholysis of naturally occurring imides: misleading interpretation of antifungal activities. J Nat Prod. 2010 Aug 27;73(8):1389-93. doi: 10.1021/np1003092. [PubMed:20701297  ] 
  6. LOTUS database [Link]