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Showing NP-Card for (1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde (NP0219879)

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Record Information
Version2.0
Created at2022-09-05 21:01:04 UTC
Updated at2022-09-05 21:01:04 UTC
NP-MRD IDNP0219879
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde
Description (1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde is found in Nidula candida.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)


  Mrv1652309052223012D          

 20 22  0  0  1  0            999 V2000
   -0.6674    1.3099    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
    0.7846    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 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
    3.2065   -0.4849    0.0000 C   0  0  1  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
    4.6276   -0.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5414   -1.4548    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2088   -1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -1.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -1.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203   -1.3054    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
    0.7846   -0.2549    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
  7 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
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3D MOL for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)

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3D SDF for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)

  Mrv1652309052223012D          

 20 22  0  0  1  0            999 V2000
   -0.6674    1.3099    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
    0.7846    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 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
    3.2065   -0.4849    0.0000 C   0  0  1  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
    4.6276   -0.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5414   -1.4548    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.2088   -1.9397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -1.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7877   -1.7903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1203   -1.3054    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
    0.7846   -0.2549    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
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  2  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
  8 15  1  0  0  0  0
  7 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  2  0  0  0  0
  4 18  1  0  0  0  0
 18 19  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0219879

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C[C@]2(OC=C([C@H]3CC[C@@H](CC3)C=O)C2=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-9-6-15(20-14(9)18)13(17)12(8-19-15)11-4-2-10(7-16)3-5-11/h6-8,10-11H,2-5H2,1H3/t10-,11-,15-/m0/s1

> <INCHI_KEY>
NQSKLGFKNUGTFE-PGUXBMHVSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.666911272326217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1r,4r)-4-[(5S)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde

> <JCHEM_LOGP>
2.7727679706666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.57228252557443

> <JCHEM_PKA_STRONGEST_BASIC>
-4.974592326431084

> <JCHEM_POLAR_SURFACE_AREA>
69.67000000000002

> <JCHEM_REFRACTIVITY>
70.4652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1r,4r)-4-[(5S)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)
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PDB for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)
HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.246   2.445   0.000  0.00  0.00           C+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  O   UNK     0       3.275   2.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.740   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.740   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.986  -0.905   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.392  -0.279   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.638  -1.184   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.477  -2.716   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.723  -3.621   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.130  -2.994   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.070  -3.342   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.825  -2.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.275  -0.476   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.799  -1.941   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.246  -0.905   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16   18                                             
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   11   15                                                       
CONECT   15   14    8                                                       
CONECT   16    7    4   17                                                  
CONECT   17   16                                                            
CONECT   18    4   19                                                       
CONECT   19   18    2   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

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3D PDB for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)
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SMILES for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)
CC1=C[C@]2(OC=C([C@H]3CC[C@@H](CC3)C=O)C2=O)OC1=O
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INCHI for NP0219879 ((1r,4r)-4-[(5s)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde)
InChI=1S/C15H16O5/c1-9-6-15(20-14(9)18)13(17)12(8-19-15)11-4-2-10(7-16)3-5-11/h6-8,10-11H,2-5H2,1H3/t10-,11-,15-/m0/s1
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H16O5
Average Mass276.2880 Da
Monoisotopic Mass276.09977 Da
IUPAC Name(1r,4r)-4-[(5S)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde
Traditional Name(1r,4r)-4-[(5S)-8-methyl-4,7-dioxo-1,6-dioxaspiro[4.4]nona-2,8-dien-3-yl]cyclohexane-1-carbaldehyde
CAS Registry NumberNot Available
SMILES
CC1=C[C@]2(OC=C([C@H]3CC[C@@H](CC3)C=O)C2=O)OC1=O
InChI Identifier
InChI=1S/C15H16O5/c1-9-6-15(20-14(9)18)13(17)12(8-19-15)11-4-2-10(7-16)3-5-11/h6-8,10-11H,2-5H2,1H3/t10-,11-,15-/m0/s1
InChI KeyNQSKLGFKNUGTFE-PGUXBMHVSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Nidula candidaLOTUS Database
Chemical Taxonomy
ClassificationNot classified
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
logP2.77ChemAxon
pKa (Strongest Acidic)18.57ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area69.67 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.47 m³·mol⁻¹ChemAxon
Polarizability28.67 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
External LinksNot Available
References
General References
  1. LOTUS database [Link]