Np mrd loader

Showing NP-Card for (5r)-3-methyl-5h-pyrrole-2,5-diol (NP0184949)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version1.0
Created at2022-09-04 00:12:55 UTC
Updated at2022-09-04 00:12:55 UTC
NP-MRD IDNP0184949
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5r)-3-methyl-5h-pyrrole-2,5-diol
DescriptionJATROPHAM belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms. (5r)-3-methyl-5h-pyrrole-2,5-diol is found in Lilium candidum, Lilium hansonii and Lilium medeoloides. It was first documented in 2008 (PMID: 18691091). Based on a literature review very few articles have been published on JATROPHAM (PMID: 25504804).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)


  Mrv1652309042202122D          

  8  8  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
Download

3D MOL for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)

     RDKit          3D

 15 15  0  0  0  0  0  0  0  0999 V2000
   -1.8783   -0.8811   -0.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5253   -0.2732   -0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5157   -0.8238    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235    0.1447    0.4537 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7507   -0.3543   -0.1816 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0327    1.2662   -0.2363 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2024    1.0566   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0513    1.9356   -1.2040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6175   -0.2052    0.2912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9664   -1.8731    0.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938   -0.8620   -1.3127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5274   -1.8224    0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355    0.4906    1.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5407   -0.3759    0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5911    2.5772   -0.6288 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  3 12  1  0
  4 13  1  1
  5 14  1  0
  8 15  1  0
M  END
Download

3D SDF for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)


  Mrv1652309042202122D          

  8  8  0  0  1  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4652   -0.8227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8843    0.8843    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
  3  4  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184949

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@@H](O)N=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NO2/c1-3-2-4(7)6-5(3)8/h2,4,7H,1H3,(H,6,8)/t4-/m1/s1

> <INCHI_KEY>
DORDKUBCRPNETF-SCSAIBSYSA-N

> <FORMULA>
C5H7NO2

> <MOLECULAR_WEIGHT>
113.116

> <EXACT_MASS>
113.047678469

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
11.050269556068496

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-methyl-2H-pyrrole-2,5-diol

> <JCHEM_LOGP>
0.42505232599999987

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.936040962127475

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.798755821758822

> <JCHEM_PKA_STRONGEST_BASIC>
0.11024538399481076

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
29.105899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R)-3-methyl-5H-pyrrole-2,5-diol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)

Download
PDB for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)
HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.735  -1.536   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       0.290  -0.290   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -0.186   1.175   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.651   1.651   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    2    8                                                  
CONECT    8    7                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

Download
3D PDB for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)
Download
SMILES for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)
CC1=C[C@@H](O)N=C1O
Download
INCHI for NP0184949 ((5r)-3-methyl-5h-pyrrole-2,5-diol)
InChI=1S/C5H7NO2/c1-3-2-4(7)6-5(3)8/h2,4,7H,1H3,(H,6,8)/t4-/m1/s1
Download
View in JSmol
Synonyms
ValueSource
5-Hydroxy-3-methyl-3-pyrrolin-2-oneMeSH
Chemical FormulaC5H7NO2
Average Mass113.1160 Da
Monoisotopic Mass113.04768 Da
IUPAC Name(2R)-4-methyl-2H-pyrrole-2,5-diol
Traditional Name(5R)-3-methyl-5H-pyrrole-2,5-diol
CAS Registry NumberNot Available
SMILES
CC1=C[C@@H](O)N=C1O
InChI Identifier
InChI=1S/C5H7NO2/c1-3-2-4(7)6-5(3)8/h2,4,7H,1H3,(H,6,8)/t4-/m1/s1
InChI KeyDORDKUBCRPNETF-SCSAIBSYSA-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
Lilium candidumLOTUS Database
Lilium hansoniiLOTUS Database
Lilium medeoloidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyrrolines. Pyrrolines are compounds containing a pyrroline ring, which is a five-member unsaturated aliphatic ring with one nitrogen atom and four carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrrolines  
Sub ClassNot Available
Direct ParentPyrrolines  
Alternative Parents
Substituents
  • Pyrroline
    • 

  • Secondary carboxylic acid amide
    • 

  • Lactam
    • 

  • Carboxamide group
    • 

  • Azacycle
    • 

  • Carboxylic acid derivative
    • 

  • Alkanolamine
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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
logP0.43ChemAxon
pKa (Strongest Acidic)5.8ChemAxon
pKa (Strongest Basic)0.11ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity29.11 m³·mol⁻¹ChemAxon
Polarizability11.05 ųChemAxon
Number of Rings1ChemAxon
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 IDC00051027  
Chemspider ID2338540  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3080808  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Jovtchev G, Gateva S, Stankov A: Lilium compounds kaempferol and jatropham can modulate cytotoxic and genotoxic effects of radiomimetic zeocin in plants and human lymphocytes In vitro. Environ Toxicol. 2016 Jun;31(6):751-64. doi: 10.1002/tox.22088. Epub 2014 Dec 15. [PubMed:25504804  ] 
  2. Thomas R, Sah NK, Sharma PB: Therapeutic biology of Jatropha curcas: a mini review. Curr Pharm Biotechnol. 2008 Aug;9(4):315-24. doi: 10.2174/138920108785161505. [PubMed:18691091  ] 
  3. LOTUS database [Link]