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Showing NP-Card for microthecin (NP0220415)

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Record Information
Version2.0
Created at2022-09-05 21:43:11 UTC
Updated at2022-09-05 21:43:11 UTC
NP-MRD IDNP0220415
Secondary Accession NumbersNone
Natural Product Identification
Common Namemicrothecin
DescriptionMicrothecin belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Microthecin is an extremely weak basic (essentially neutral) compound (based on its pKa). A metabolite isolated from morels (e.G. Morchella costata) and red algae (e.G. microthecin is found in Gracilariopsis lemaneiformis, Morchella costata and Morchella esculenta. Gracilariopsis lemaneiformis).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0220415 (microthecin)


  Mrv1533004251509212D          

 10 10  0  0  0  0            999 V2000
    2.0572    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for NP0220415 (microthecin)

     RDKit          3D

 18 18  0  0  0  0  0  0  0  0999 V2000
   -0.0359   -2.1456   -1.0488 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3833   -1.1560   -0.4134 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7677   -0.7556   -0.5040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0766    0.4333   -0.0535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0676    1.3188    0.5165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1167    0.8224    0.8424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262   -0.3855    0.4352 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8058   -1.1758    1.5691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8499   -0.2333   -0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6745    0.5366   -1.4682 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5490   -1.3922   -0.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1026    0.7848   -0.0972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5352    1.8106    1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356    2.1778   -0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7878   -1.1724    1.7614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5622    0.2928    0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2147   -1.2424   -0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8441    1.4818   -1.2301 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  7  1  0
  7  8  1  1
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2  7  1  0
 10 18  1  0
  9 16  1  0
  9 17  1  0
  8 15  1  0
  5 13  1  0
  5 14  1  0
  4 12  1  0
  3 11  1  0
M  END
Download

3D SDF for NP0220415 (microthecin)


  Mrv1533004251509212D          

 10 10  0  0  0  0            999 V2000
    2.0572    1.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0220415

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC1(O)OCC=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O4/c7-4-6(9)5(8)2-1-3-10-6/h1-2,7,9H,3-4H2

> <INCHI_KEY>
FUJVJJBVXLPRQJ-UHFFFAOYSA-N

> <FORMULA>
C6H8O4

> <MOLECULAR_WEIGHT>
144.126

> <EXACT_MASS>
144.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
12.939334821603945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-one

> <ALOGPS_LOGP>
-0.80

> <JCHEM_LOGP>
-0.2027483686666668

> <ALOGPS_LOGS>
0.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.304779907096965

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.583451924613824

> <JCHEM_PKA_STRONGEST_BASIC>
-3.49332812538647

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
34.0628

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.80e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
microthecin

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0220415 (microthecin)

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PDB for NP0220415 (microthecin)
HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  O   UNK     0       3.840   3.222   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    9                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0220415 (microthecin)
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SMILES for NP0220415 (microthecin)
OCC1(O)OCC=CC1=O
Download
INCHI for NP0220415 (microthecin)
InChI=1S/C6H8O4/c7-4-6(9)5(8)2-1-3-10-6/h1-2,7,9H,3-4H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC6H8O4
Average Mass144.1260 Da
Monoisotopic Mass144.04226 Da
IUPAC Name2-hydroxy-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-one
Traditional Namemicrothecin
CAS Registry NumberNot Available
SMILES
OCC1(O)OCC=CC1=O
InChI Identifier
InChI=1S/C6H8O4/c7-4-6(9)5(8)2-1-3-10-6/h1-2,7,9H,3-4H2
InChI KeyFUJVJJBVXLPRQJ-UHFFFAOYSA-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
Gracilaria lemaneiformisLOTUS Database
Morchella costataLOTUS Database
Morchella esculentaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrans  
Sub ClassPyranones and derivatives  
Direct ParentDihydropyranones  
Alternative Parents
Substituents
  • Dihydropyranone
    • 

  • Acyloin
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Hemiacetal
    • 

  • Oxacycle
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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-0.8ALOGPS
logP-0.2ChemAxon
logS0.29ALOGPS
pKa (Strongest Acidic)9.58ChemAxon
pKa (Strongest Basic)-3.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.06 m³·mol⁻¹ChemAxon
Polarizability12.94 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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDC19821  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10130020  
PDB IDNot Available
ChEBI ID51835  
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]