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Showing NP-Card for (5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione (NP0222383)

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Record Information
Version2.0
Created at2022-09-06 00:12:25 UTC
Updated at2022-09-06 00:12:25 UTC
NP-MRD IDNP0222383
Secondary Accession NumbersNone
Natural Product Identification
Common Name(5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione
DescriptionDimethylgloiosiphone A belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. (5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione is found in Gloiosiphonia verticillaris. Based on a literature review very few articles have been published on dimethylgloiosiphone A.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)


  Mrv1652309062202122D          

 19 20  0  0  1  0            999 V2000
    0.5984   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -1.6761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -1.0086    0.0000 C   0  0  0  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
    1.4991   -0.6674    0.0000 O   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
   -0.6674   -0.4849    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
    1.7545    1.0799    0.0000 C   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
    3.2065    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203    2.1304    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
    3.2065   -0.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -0.1494    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
    1.7545   -1.0799    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
  4  3  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
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3D MOL for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)

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3D SDF for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)

  Mrv1652309062202122D          

 19 20  0  0  1  0            999 V2000
    0.5984   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -1.6761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491   -1.0086    0.0000 C   0  0  0  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
    1.4991   -0.6674    0.0000 O   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
   -0.6674   -0.4849    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
    1.7545    1.0799    0.0000 C   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
    3.2065    1.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203    2.1304    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
    3.2065   -0.4849    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9602   -0.1494    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
    1.7545   -1.0799    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
  4  3  1  1  0  0  0
  4  5  1  6  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
 10 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC[C@@]1(O)C(=O)CC[C@@]11CC(OC)=C(OC)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O6/c1-17-7-13(16)9(14)4-5-12(13)6-8(18-2)10(19-3)11(12)15/h16H,4-7H2,1-3H3/t12-,13+/m0/s1

> <INCHI_KEY>
QLPFPDLYGCZCSW-QWHCGFSZSA-N

> <FORMULA>
C13H18O6

> <MOLECULAR_WEIGHT>
270.281

> <EXACT_MASS>
270.1103383

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.0053172045221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5R,6R)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione

> <JCHEM_LOGP>
-0.41928992766666695

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.32720715948679

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.742675415141337

> <JCHEM_PKA_STRONGEST_BASIC>
-4.003188551281011

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
67.7189

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)
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PDB for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.117  -4.535   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.743  -3.129   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.838  -1.883   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.465  -0.476   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.798  -1.246   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.246  -0.905   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.465   2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.275   2.016   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.986   2.445   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.825   3.977   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.740  -0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.986  -0.905   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.392  -0.279   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.275  -2.016   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6   10                                             
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11   18                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15   10   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

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3D PDB for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)
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SMILES for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)
COC[C@@]1(O)C(=O)CC[C@@]11CC(OC)=C(OC)C1=O
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INCHI for NP0222383 ((5r,6r)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione)
InChI=1S/C13H18O6/c1-17-7-13(16)9(14)4-5-12(13)6-8(18-2)10(19-3)11(12)15/h16H,4-7H2,1-3H3/t12-,13+/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC13H18O6
Average Mass270.2810 Da
Monoisotopic Mass270.11034 Da
IUPAC Name(5R,6R)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione
Traditional Name(5R,6R)-6-hydroxy-2,3-dimethoxy-6-(methoxymethyl)spiro[4.4]non-2-ene-1,7-dione
CAS Registry NumberNot Available
SMILES
COC[C@@]1(O)C(=O)CC[C@@]11CC(OC)=C(OC)C1=O
InChI Identifier
InChI=1S/C13H18O6/c1-17-7-13(16)9(14)4-5-12(13)6-8(18-2)10(19-3)11(12)15/h16H,4-7H2,1-3H3/t12-,13+/m0/s1
InChI KeyQLPFPDLYGCZCSW-QWHCGFSZSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Gloiosiphonia verticillarisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups.
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassCarbonyl compounds  
Direct ParentAcyloins  
Alternative Parents
Substituents
  • Acyloin
    • 

  • Vinylogous ester
    • 

  • Tertiary alcohol
    • 

  • Cyclic alcohol
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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-0.42ChemAxon
pKa (Strongest Acidic)11.74ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area82.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity67.72 m³·mol⁻¹ChemAxon
Polarizability27.01 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 ID9087831  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10912574  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]