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Showing NP-Card for Moniliformin (NP0021481)

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Record Information
Version2.0
Created at2021-01-06 06:45:50 UTC
Updated at2021-07-15 17:36:28 UTC
NP-MRD IDNP0021481
Secondary Accession NumbersNone
Natural Product Identification
Common NameMoniliformin
Provided ByNPAtlasNPAtlas Logo
DescriptionMoniliformin belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety. Moniliformin is found in Fusarium and Fusarium sporotrichioides. Moniliformin was first documented in 1974 (PMID: 4833647). Based on a literature review very few articles have been published on Moniliformin.
Structure
Data?1624506845
MOL3D MOLSDF3D SDFPDBSMILESInChI

MOL for NP0021481 (Moniliformin)


  Mrv1652306242105163D          

  9  9  0  0  0  0            999 V2000
   -2.5233   -0.4990   -0.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819   -0.2057   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.9424    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921    0.2311    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    0.5195    0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620    0.9564   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157    2.1995   -0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -2.0157    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -0.2435    0.1072 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  2  1  0  0  0  0
  3  8  1  0  0  0  0
  5  9  1  0  0  0  0
M  END
Download

3D MOL for NP0021481 (Moniliformin)

     RDKit          3D

  9  9  0  0  0  0  0  0  0  0999 V2000
   -2.5233   -0.4990   -0.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819   -0.2057   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.9424    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921    0.2311    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    0.5195    0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620    0.9564   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157    2.1995   -0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -2.0157    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -0.2435    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  2  1  0
  3  8  1  0
  5  9  1  0
M  END
Download

3D SDF for NP0021481 (Moniliformin)


  Mrv1652306242105163D          

  9  9  0  0  0  0            999 V2000
   -2.5233   -0.4990   -0.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819   -0.2057   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.9424    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921    0.2311    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    0.5195    0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620    0.9564   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157    2.1995   -0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -2.0157    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -0.2435    0.1072 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  2  1  0  0  0  0
  3  8  1  0  0  0  0
  5  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021481

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H

> <INCHI_KEY>
KGPQKNJSZNXOPV-UHFFFAOYSA-N

> <FORMULA>
C4H2O3

> <MOLECULAR_WEIGHT>
98.0569

> <EXACT_MASS>
98.00039393

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
8.081167736317035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxycyclobut-3-ene-1,2-dione

> <ALOGPS_LOGP>
-0.21

> <JCHEM_LOGP>
0.2826188920000001

> <ALOGPS_LOGS>
0.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.316463993713413

> <JCHEM_PKA_STRONGEST_BASIC>
-4.965438649149754

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
22.8278

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.50e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
moniliformin

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0021481 (Moniliformin)

     RDKit          3D

  9  9  0  0  0  0  0  0  0  0999 V2000
   -2.5233   -0.4990   -0.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819   -0.2057   -0.0404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1234   -0.9424    0.0301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921    0.2311    0.0136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9704    0.5195    0.0545 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5620    0.9564   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157    2.1995   -0.1114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1145   -2.0157    0.0784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6294   -0.2435    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  6  2  1  0
  3  8  1  0
  5  9  1  0
M  END
Download

PDB for NP0021481 (Moniliformin)

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  O   UNK     0      -2.523  -0.499  -0.076  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.282  -0.206  -0.040  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.123  -0.942   0.030  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.592   0.231   0.014  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.970   0.520   0.055  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.562   0.956  -0.056  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.816   2.200  -0.111  0.00  0.00           O+0
HETATM    8  H   UNK     0       0.115  -2.016   0.078  0.00  0.00           H+0
HETATM    9  H   UNK     0       2.629  -0.244   0.107  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4    9                                                       
CONECT    6    4    7    2                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
CONECT    9    5                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
Download

3D PDB for NP0021481 (Moniliformin)

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SMILES for NP0021481 (Moniliformin)
[H]OC1=C([H])C(=O)C1=O
Download
INCHI for NP0021481 (Moniliformin)
InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
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View in JSmolView NMR Assignments
Synonyms
ValueSource
Moniliformin, potassium saltMeSH
Moniliformin, sodium saltMeSH
Chemical FormulaC4H2O3
Average Mass98.0569 Da
Monoisotopic Mass98.00039 Da
IUPAC Name3-hydroxycyclobut-3-ene-1,2-dione
Traditional Namemoniliformin
CAS Registry NumberNot Available
SMILES
OC1=CC(=O)C1=O
InChI Identifier
InChI=1S/C4H2O3/c5-2-1-3(6)4(2)7/h1,5H
InChI KeyKGPQKNJSZNXOPV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dendrobium moniliformeKNApSAcK Database
FusariumNPAtlas
Fusarium sporotrichioidesLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as vinylogous acids. These are organic compounds containing a hydroxyl group, which is indirectly attached to a carbonyl via an intervening vinyl (>C=C<) moiety.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassVinylogous acids  
Sub ClassNot Available
Direct ParentVinylogous acids  
Alternative Parents
Substituents
  • Vinylogous acid
    • 

  • Cyclic ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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-0.21ALOGPS
logP0.28ChemAxon
logS0.19ALOGPS
pKa (Strongest Acidic)6.32ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity22.83 m³·mol⁻¹ChemAxon
Polarizability8.08 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
NPAtlas IDNPA028987  
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00034062  
Chemspider ID36957  
KEGG Compound IDC20592  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMoniliformin  
METLIN IDNot Available
PubChem Compound40452  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Springer JP, Clardy J, Cole RJ, Kirksey JW, Hill RK, Carlson MR, Isidor JL: Structure and synthesis of moniliformin, a novel cyclobutane microbial toxin. J Am Chem Soc. 1974 Apr 3;96(7):2267-8. doi: 10.1021/ja00814a055. [PubMed:4833647  ]