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Showing NP-Card for (3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione (NP0290841)

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Record Information
Version2.0
Created at2022-09-09 21:42:33 UTC
Updated at2022-09-09 21:42:33 UTC
NP-MRD IDNP0290841
Secondary Accession NumbersNone
Natural Product Identification
Common Name(3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione
DescriptionXylobovide belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. (3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione is found in Xylaria obovata. (3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione was first documented in 2001 (PMID: 11483061). Based on a literature review very few articles have been published on Xylobovide.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)


  Mrv1652309092223422D          

 13 14  0  0  1  0            999 V2000
   -0.2549    0.7846    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
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242    0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   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
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
M  END
Download

3D MOL for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)

     RDKit          3D

 23 24  0  0  0  0  0  0  0  0999 V2000
    3.3932    0.8235    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2162    0.5211    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7097    1.0091   -1.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3746    1.6082   -1.9643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3390    0.6891   -1.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0986    0.3432    0.1864 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1455   -0.3452    0.7630 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0731   -1.6620    0.0983 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9832   -2.5307    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1884   -1.7919   -0.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0387   -0.8357    0.0948 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2255   -0.5023   -0.7599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803    0.5057   -0.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0585    1.4715    0.2121 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6982    0.4220    1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4535    1.1582    0.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1157   -0.3892    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3121   -1.2398    1.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8129   -1.4269   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8474   -0.1568   -1.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7611    0.7229    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1413    1.4603   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1470    0.1459    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  2  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6 11  1  0
  2  7  1  0
 13 21  1  0
 13 22  1  0
 13 23  1  0
 12 19  1  0
 12 20  1  0
 11 18  1  1
  7 17  1  1
  6 16  1  1
  1 14  1  0
  1 15  1  0
M  END
Download

3D SDF for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)


  Mrv1652309092223422D          

 13 14  0  0  1  0            999 V2000
   -0.2549    0.7846    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
   -0.4849   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3099   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5692    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8242    0.7846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5692   -1.3349    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8242   -2.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6312   -2.2910    0.0000 C   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
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0290841

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@H]1OC(=O)[C@@H]2[C@H]1OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-3-5-7-6(9(11)12-5)4(2)8(10)13-7/h5-7H,2-3H2,1H3/t5-,6+,7+/m1/s1

> <INCHI_KEY>
BHRJNZZWSGMQLJ-VQVTYTSYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.175

> <EXACT_MASS>
182.057908802

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.168194525825

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6R,6aR)-6-ethyl-3-methylidene-hexahydrofuro[2,3-c]furan-2,4-dione

> <JCHEM_LOGP>
1.1860778639999998

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.87007547114386

> <JCHEM_PKA_STRONGEST_BASIC>
-6.711492171360851

> <JCHEM_POLAR_SURFACE_AREA>
52.60000000000001

> <JCHEM_REFRACTIVITY>
42.18500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6R,6aR)-6-ethyl-3-methylidene-dihydro-3aH-furo[2,3-c]furan-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)

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PDB for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)
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      -0.476   1.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.905  -1.246   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.445  -1.246   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.000  -2.492   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.465  -2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.405   1.465   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.834  -1.246   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.929  -2.492   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.405  -3.956   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.911  -4.277   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

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3D PDB for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)
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SMILES for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)
CC[C@H]1OC(=O)[C@@H]2[C@H]1OC(=O)C2=C
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INCHI for NP0290841 ((3as,6r,6ar)-6-ethyl-3-methylidene-dihydro-3ah-furo[2,3-c]furan-2,4-dione)
InChI=1S/C9H10O4/c1-3-5-7-6(9(11)12-5)4(2)8(10)13-7/h5-7H,2-3H2,1H3/t5-,6+,7+/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC9H10O4
Average Mass182.1750 Da
Monoisotopic Mass182.05791 Da
IUPAC Name(3aS,6R,6aR)-6-ethyl-3-methylidene-hexahydrofuro[2,3-c]furan-2,4-dione
Traditional Name(3aS,6R,6aR)-6-ethyl-3-methylidene-dihydro-3aH-furo[2,3-c]furan-2,4-dione
CAS Registry NumberNot Available
SMILES
CC[C@H]1OC(=O)[C@@H]2[C@H]1OC(=O)C2=C
InChI Identifier
InChI=1S/C9H10O4/c1-3-5-7-6(9(11)12-5)4(2)8(10)13-7/h5-7H,2-3H2,1H3/t5-,6+,7+/m1/s1
InChI KeyBHRJNZZWSGMQLJ-VQVTYTSYSA-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
Xylaria obovataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as furofurans. These are organic compounds containing a two furan rings fused to each other. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassFurofurans  
Sub ClassNot Available
Direct ParentFurofurans  
Alternative Parents
Substituents
  • Furofuran
    • 

  • Dicarboxylic acid or derivatives
    • 

  • Gamma butyrolactone
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Oxolane
    • 

  • Carboxylic acid ester
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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
logP1.19ChemAxon
pKa (Strongest Acidic)18.87ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity42.18 m³·mol⁻¹ChemAxon
Polarizability17.17 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID8758944  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10583566  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yu M, Lynch V, Pagenkopf BL: Intramolecular cyclopropanation of glycals: studies toward the synthesis of canadensolide, sporothriolide, and xylobovide. Org Lett. 2001 Aug 9;3(16):2563-6. doi: 10.1021/ol016239h. [PubMed:11483061  ] 
  2. LOTUS database [Link]