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Showing NP-Card for (5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione (NP0323002)

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Record Information
Version2.0
Created at2022-09-12 02:08:22 UTC
Updated at2022-09-12 02:08:23 UTC
NP-MRD IDNP0323002
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione
Description(?)-Longianone belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. (5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione is found in Taxus mairei and Xylaria longiana. Based on a literature review very few articles have been published on (?)-Longianone.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)


  Mrv1652309122204082D          

 11 12  0  0  1  0            999 V2000
   -0.6674    1.3099    0.0000 O   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
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -1.0396    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)

     RDKit          3D

 17 18  0  0  0  0  0  0  0  0999 V2000
   -3.0046   -1.0201    1.1284 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1740   -0.4192    0.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9127   -1.0240   -0.0992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0157    0.2193   -0.0795 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9443    1.2514   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2110    0.8706   -0.1067 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429    0.4961    1.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7298    0.0347    1.3276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2520   -0.2572    0.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171    0.0364   -0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3183    0.1241   -2.0824 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5276   -1.8280    0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0523   -1.2867   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9431    1.2532   -1.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7115    2.2780   -0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2744   -0.0845    2.2566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2624   -0.6441   -0.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  1
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  6  2  1  0
 10  4  1  0
  3 12  1  0
  3 13  1  0
  5 14  1  0
  5 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)


  Mrv1652309122204082D          

 11 12  0  0  1  0            999 V2000
   -0.6674    1.3099    0.0000 O   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
    0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5391    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7545   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4995   -1.0396    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  4  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0323002

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1C[C@@]2(CO1)OC=CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H6O4/c8-5-1-2-11-7(5)3-6(9)10-4-7/h1-2H,3-4H2/t7-/m0/s1

> <INCHI_KEY>
VVAVPMFPYRLMED-ZETCQYMHSA-N

> <FORMULA>
C7H6O4

> <MOLECULAR_WEIGHT>
154.121

> <EXACT_MASS>
154.026608673

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.326497966427379

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5S)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione

> <JCHEM_LOGP>
0.06359613266666661

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.34530373194837

> <JCHEM_PKA_STRONGEST_BASIC>
-4.832529787944241

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
34.306400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)

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PDB for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)
HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.246   2.445   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.000   0.000   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       3.275   2.016   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.740   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.799  -1.941   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7   10                                             
CONECT    5    4    6                                                       
CONECT    6    5    2                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)
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SMILES for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)
O=C1C[C@@]2(CO1)OC=CC2=O
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INCHI for NP0323002 ((5s)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione)
InChI=1S/C7H6O4/c8-5-1-2-11-7(5)3-6(9)10-4-7/h1-2H,3-4H2/t7-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC7H6O4
Average Mass154.1210 Da
Monoisotopic Mass154.02661 Da
IUPAC Name(5S)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione
Traditional Name(5S)-1,7-dioxaspiro[4.4]non-2-ene-4,8-dione
CAS Registry NumberNot Available
SMILES
O=C1C[C@@]2(CO1)OC=CC2=O
InChI Identifier
InChI=1S/C7H6O4/c8-5-1-2-11-7(5)3-6(9)10-4-7/h1-2H,3-4H2/t7-/m0/s1
InChI KeyVVAVPMFPYRLMED-ZETCQYMHSA-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
Taxus maireiLOTUS Database
Xylaria longianaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassLactones  
Sub ClassGamma butyrolactones  
Direct ParentGamma butyrolactones  
Alternative Parents
Substituents
  • 3-furanone
    • 

  • Gamma butyrolactone
    • 

  • Dihydrofuran
    • 

  • Vinylogous ester
    • 

  • Tetrahydrofuran
    • 

  • Carboxylic acid ester
    • 

  • Ketone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • 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
logP0.064ChemAxon
pKa (Strongest Acidic)19.35ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.31 m³·mol⁻¹ChemAxon
Polarizability13.33 ųChemAxon
Number of Rings2ChemAxon
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 ID554859  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBracket  
METLIN IDNot Available
PubChem Compound639435  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]