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Showing NP-Card for Norbadione A (NP0047942)

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Record Information
Version1.0
Created at2022-03-17 20:48:28 UTC
Updated at2022-03-17 20:48:28 UTC
NP-MRD IDNP0047942
Secondary Accession NumbersNone
Natural Product Identification
Common NameNorbadione A
DescriptionNorbadione A belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. Norbadione A is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, norbadione a has been detected, but not quantified in, mushrooms. This could make norbadione a a potential biomarker for the consumption of these foods. There is a pH-dependent Z to E isomer switch that occurs in both pulvinate moieties, which yields four stereoisomeric forms (E/E, E/Z, Z/Z, Z/E). A series of alkali chelators based on the structure of norbadione A has been reported. The molecule has also been reported as a potassium salt from the mushrooms Pisolithus tinctorius (horse dung fungus) and Chalciporus piperatus. Bourdreux and colleagues reported a total synthesis of norbadione A in 2008. These functional groups confer water-solubility to the molecule. It has been investigated for its ability to provide a protective effect against the damaging effects of ionizing radiation, an effect attributed to its ability to protect DNA-related targets from irradiation. A polyphenol, norbadione A is related to a family of mushroom pigments known as pulvinic acids.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0047942 (Norbadione A)


  Mrv0541 05061307452D          

 50 56  0  0  0  0            999 V2000
   -3.5319   -0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8376   -0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486   -3.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956   -4.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1727    0.0120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0143   -0.9804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3018   -1.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1286    0.2571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 50 30  1  0  0  0  0
 50 35  1  0  0  0  0
M  END
Download

3D MOL for NP0047942 (Norbadione A)

Download
3D SDF for NP0047942 (Norbadione A)

  Mrv0541 05061307452D          

 50 56  0  0  0  0            999 V2000
   -3.5319   -0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8376   -0.7419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7486   -3.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8956   -4.7396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.5839   -0.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6365   -2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.8927   -3.4881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  1  1  0  0  0  0
  6  2  2  0  0  0  0
  7  3  1  0  0  0  0
  8  4  2  0  0  0  0
 12  1  2  0  0  0  0
 12  2  1  0  0  0  0
 13  3  2  0  0  0  0
 13  4  1  0  0  0  0
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 37 16  1  0  0  0  0
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 39 26  1  0  0  0  0
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 41 31  2  0  0  0  0
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 43 32  2  0  0  0  0
 44 32  1  0  0  0  0
 45 33  2  0  0  0  0
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 47 35  2  0  0  0  0
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 50 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047942

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(=C1/OC(=O)C(=C1O)C1=CC2=C3C(OC(=O)C3=C1)=C(O)C=C2C1=C(O)\C(OC1=O)=C(\C(O)=O)C1=CC=C(O)C=C1)\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C35H18O15/c36-15-5-1-12(2-6-15)22(31(41)42)29-26(39)21(34(46)49-29)14-9-17-18(11-20(38)28-24(17)19(10-14)33(45)48-28)25-27(40)30(50-35(25)47)23(32(43)44)13-3-7-16(37)8-4-13/h1-11,36-40H,(H,41,42)(H,43,44)/b29-22-,30-23-

> <INCHI_KEY>
NEAFOYGNZAYARY-TVUQKFFQSA-N

> <FORMULA>
C35H18O15

> <MOLECULAR_WEIGHT>
678.5084

> <EXACT_MASS>
678.064569906

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
64.57270783712988

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2Z)-4-{6-[(5Z)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),4,6,8(12),9-pentaen-9-yl}-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
3.940301529

> <ALOGPS_LOGS>
-4.77

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.7476393574324143

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.1455645457617494

> <JCHEM_PKA_STRONGEST_BASIC>
-4.400536940547782

> <JCHEM_POLAR_SURFACE_AREA>
254.64999999999992

> <JCHEM_REFRACTIVITY>
170.3242000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2Z)-4-{6-[(5Z)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),4,6,8(12),9-pentaen-9-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0047942 (Norbadione A)
Download
PDB for NP0047942 (Norbadione A)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -6.593  -0.301   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.030  -1.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.397  -6.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.672  -8.847   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.218   1.106   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.656   0.022   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.929  -6.035   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.204  -8.689   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.240  -2.600   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.570  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.760  -1.830   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.499  -1.547   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.769  -7.600   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.570  -1.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.750   1.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.832  -7.283   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.090  -1.830   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.430  -2.600   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.240   0.480   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.760  -0.290   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.904  -2.599   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.873  -2.954   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.763  -7.758   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.090  -0.290   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.432  -4.140   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.311  -1.972   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.188  -5.047   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.430   0.480   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.342  -3.116   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.666  -6.511   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.779  -4.199   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.392  -9.164   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       0.320   2.080   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.066  -4.131   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.680  -5.043   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -9.375   2.675   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -5.364  -7.125   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       5.094   0.479   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -4.630  -0.465   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -0.277  -4.574   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -7.154  -5.607   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -9.311  -4.037   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       2.924  -9.323   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       0.489 -10.412   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -0.571   3.336   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -1.922  -5.162   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       5.144  -4.565   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0       1.860   2.080   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -4.573  -4.450   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       3.206  -6.509   0.000  0.00  0.00           O+0
CONECT    1    5   12                                                       
CONECT    2    6   12                                                       
CONECT    3    7   13                                                       
CONECT    4    8   13                                                       
CONECT    5    1   15                                                       
CONECT    6    2   15                                                       
CONECT    7    3   16                                                       
CONECT    8    4   16                                                       
CONECT    9   14   17                                                       
CONECT   10   14   19                                                       
CONECT   11   18   20                                                       
CONECT   12    1    2   22                                                  
CONECT   13    3    4   23                                                  
CONECT   14    9   10   21                                                  
CONECT   15    5    6   36                                                  
CONECT   16    7    8   37                                                  
CONECT   17    9   18   24                                                  
CONECT   18   11   17   25                                                  
CONECT   19   10   24   33                                                  
CONECT   20   11   28   38                                                  
CONECT   21   14   26   34                                                  
CONECT   22   12   29   31                                                  
CONECT   23   13   30   32                                                  
CONECT   24   17   19   28                                                  
CONECT   25   18   27   35                                                  
CONECT   26   21   29   39                                                  
CONECT   27   25   30   40                                                  
CONECT   28   20   24   48                                                  
CONECT   29   22   26   49                                                  
CONECT   30   23   27   50                                                  
CONECT   31   22   41   42                                                  
CONECT   32   23   43   44                                                  
CONECT   33   19   45   48                                                  
CONECT   34   21   46   49                                                  
CONECT   35   25   47   50                                                  
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   20                                                            
CONECT   39   26                                                            
CONECT   40   27                                                            
CONECT   41   31                                                            
CONECT   42   31                                                            
CONECT   43   32                                                            
CONECT   44   32                                                            
CONECT   45   33                                                            
CONECT   46   34                                                            
CONECT   47   35                                                            
CONECT   48   28   33                                                       
CONECT   49   29   34                                                       
CONECT   50   30   35                                                       
MASTER        0    0    0    0    0    0    0    0   50    0  112    0
END

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3D PDB for NP0047942 (Norbadione A)
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SMILES for NP0047942 (Norbadione A)
OC(=O)C(=C1/OC(=O)C(=C1O)C1=CC2=C3C(OC(=O)C3=C1)=C(O)C=C2C1=C(O)\C(OC1=O)=C(\C(O)=O)C1=CC=C(O)C=C1)\C1=CC=C(O)C=C1
Download
INCHI for NP0047942 (Norbadione A)
InChI=1S/C35H18O15/c36-15-5-1-12(2-6-15)22(31(41)42)29-26(39)21(34(46)49-29)14-9-17-18(11-20(38)28-24(17)19(10-14)33(45)48-28)25-27(40)30(50-35(25)47)23(32(43)44)13-3-7-16(37)8-4-13/h1-11,36-40H,(H,41,42)(H,43,44)/b29-22-,30-23-
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View in JSmol
Synonyms
ValueSource
Pulvinic acid derivativeHMDB
2-[(2Z)-4-{9-[(5Z)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),4,6,8(12),9-pentaen-6-yl}-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetateGenerator
Chemical FormulaC35H18O15
Average Mass678.5084 Da
Monoisotopic Mass678.06457 Da
IUPAC Name2-[(2Z)-4-{6-[(5Z)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxo-2,5-dihydrofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),4,6,8(12),9-pentaen-9-yl}-3-hydroxy-5-oxo-2,5-dihydrofuran-2-ylidene]-2-(4-hydroxyphenyl)acetic acid
Traditional Name[(2Z)-4-{6-[(5Z)-5-[carboxy(4-hydroxyphenyl)methylidene]-4-hydroxy-2-oxofuran-3-yl]-11-hydroxy-3-oxo-2-oxatricyclo[6.3.1.0⁴,¹²]dodeca-1(11),4,6,8(12),9-pentaen-9-yl}-3-hydroxy-5-oxofuran-2-ylidene](4-hydroxyphenyl)acetic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=C1/OC(=O)C(=C1O)C1=CC2=C3C(OC(=O)C3=C1)=C(O)C=C2C1=C(O)\C(OC1=O)=C(\C(O)=O)C1=CC=C(O)C=C1)\C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C35H18O15/c36-15-5-1-12(2-6-15)22(31(41)42)29-26(39)21(34(46)49-29)14-9-17-18(11-20(38)28-24(17)19(10-14)33(45)48-28)25-27(40)30(50-35(25)47)23(32(43)44)13-3-7-16(37)8-4-13/h1-11,36-40H,(H,41,42)(H,43,44)/b29-22-,30-23-
InChI KeyNEAFOYGNZAYARY-TVUQKFFQSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassPentacarboxylic acids and derivatives  
Direct ParentPentacarboxylic acids and derivatives  
Alternative Parents
Substituents
  • Pentacarboxylic acid or derivatives
    • 

  • 2-naphthol
    • 

  • Naphthalene
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Phenol
    • 

  • Monocyclic benzene moiety
    • 

  • 2-furanone
    • 

  • Benzenoid
    • 

  • Dihydrofuran
    • 

  • Enol ester
    • 

  • Vinylogous acid
    • 

  • Enoate ester
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Lactone
    • 

  • Carboxylic acid ester
    • 

  • Oxacycle
    • 

  • Enol
    • 

  • Carboxylic acid
    • 

  • Organoheterocyclic compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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
logP3.07ALOGPS
logP3.94ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)2.15ChemAxon
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area254.65 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity170.32 m³·mol⁻¹ChemAxon
Polarizability64.57 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDHMDB0034350  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012711  
KNApSAcK IDNot Available
Chemspider ID30777048  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNorbadione A  
METLIN IDNot Available
PubChem Compound97047014  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available