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Showing NP-Card for (5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde (NP0252728)

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Record Information
Version2.0
Created at2022-09-07 16:19:45 UTC
Updated at2022-09-07 16:19:45 UTC
NP-MRD IDNP0252728
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde
DescriptionCanangone 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. (5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde is found in Cananga odorata. (5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde was first documented in 2002 (PMID: 11754546). Based on a literature review very few articles have been published on Canangone.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)


  Mrv1652309072218192D          

 14 15  0  0  1  0            999 V2000
    4.1570    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695   -1.0164    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   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
    1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
Download

3D MOL for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)

     RDKit          3D

 26 27  0  0  0  0  0  0  0  0999 V2000
    4.2946   -0.5420   -0.7818 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6180    0.2125   -0.0559 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1678    0.1969   -0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625    1.0058    0.6963 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0010    1.0671    0.7445 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3920    2.3197    0.2700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6997    0.0099   -0.0255 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8971   -0.5632    0.7460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213   -0.7480   -0.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6896    0.3337   -1.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228    0.5643   -1.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7746    1.1580   -2.2068 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1967   -1.1674   -0.3262 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4842   -0.7430   -0.9981 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1205    0.8946    0.6090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0242    1.6637    1.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3474    1.0180    1.8020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2216    2.6260    0.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6637   -1.5240    1.2059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473    0.1220    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8211   -1.6953   -0.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9264   -0.7087    0.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4797   -1.6066    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -1.9309   -0.8743 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1149   -1.6528   -1.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3179   -0.3101   -1.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  1  0
  4  3  2  0
  3 14  1  0
 14 13  1  0
 13  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
  3  2  1  0
  2  1  2  0
  7  5  1  0
  7 11  1  6
  6 18  1  0
  5 17  1  1
  4 16  1  0
 14 25  1  0
 14 26  1  0
 13 23  1  0
 13 24  1  0
  8 19  1  0
  8 20  1  0
  9 21  1  0
  9 22  1  0
  2 15  1  0
M  END
Download

3D SDF for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)


  Mrv1652309072218192D          

 14 15  0  0  1  0            999 V2000
    4.1570    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7445    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9195    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820   -0.3020    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2695   -1.0164    0.0000 O   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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 O   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
    1.0396    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6820    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070    1.1270    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
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0252728

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1C=C(CC[C@@]11CCOC1=O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c11-6-7-1-2-10(8(12)5-7)3-4-14-9(10)13/h5-6,8,12H,1-4H2/t8-,10-/m1/s1

> <INCHI_KEY>
NOJVXIYSKYICFF-PSASIEDQSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.202

> <EXACT_MASS>
196.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.083092539043022

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,6R)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde

> <JCHEM_LOGP>
-0.041855666999999624

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.021823739825805

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2266542962001914

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
48.9363

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)

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PDB for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)
HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  O   UNK     0       7.760   2.104   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.990   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.450   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.680  -0.564   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.140  -0.564   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.370  -1.897   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.941   3.481   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.140   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.680   2.104   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   11   13                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11                                                            
CONECT   13    7   14                                                       
CONECT   14   13    3                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

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3D PDB for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)
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SMILES for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)
O[C@@H]1C=C(CC[C@@]11CCOC1=O)C=O
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INCHI for NP0252728 ((5r,6r)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde)
InChI=1S/C10H12O4/c11-6-7-1-2-10(8(12)5-7)3-4-14-9(10)13/h5-6,8,12H,1-4H2/t8-,10-/m1/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC10H12O4
Average Mass196.2020 Da
Monoisotopic Mass196.07356 Da
IUPAC Name(5R,6R)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde
Traditional Name(5R,6R)-6-hydroxy-1-oxo-2-oxaspiro[4.5]dec-7-ene-8-carbaldehyde
CAS Registry NumberNot Available
SMILES
O[C@@H]1C=C(CC[C@@]11CCOC1=O)C=O
InChI Identifier
InChI=1S/C10H12O4/c11-6-7-1-2-10(8(12)5-7)3-4-14-9(10)13/h5-6,8,12H,1-4H2/t8-,10-/m1/s1
InChI KeyNOJVXIYSKYICFF-PSASIEDQSA-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
Cananga odorataLOTUS 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
  • Gamma butyrolactone
    • 

  • Oxolane
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • Alcohol
    • 

  • 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
logP-0.042ChemAxon
pKa (Strongest Acidic)14.02ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.94 m³·mol⁻¹ChemAxon
Polarizability19.08 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 IDC00054263  
Chemspider ID9205894  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11030720  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Caloprisco E, Fourneron JD, Faure R, Demarne FE: Unusual lactones from Cananga odorata (Annonaceae). J Agric Food Chem. 2002 Jan 2;50(1):78-80. doi: 10.1021/jf0105079. [PubMed:11754546  ] 
  2. LOTUS database [Link]