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Showing NP-Card for Grevilline D (NP0047582)

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Record Information
Version2.0
Created at2022-03-17 20:42:32 UTC
Updated at2022-03-17 20:42:33 UTC
NP-MRD IDNP0047582
Secondary Accession NumbersNone
Natural Product Identification
Common NameGrevilline D
DescriptionGrevilline D belongs to the class of organic compounds known as hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4. Grevilline D is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Grevilline D has been detected, but not quantified in, mushrooms. This could make grevilline D a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047582 (Grevilline D)


  Mrv0541 05061307002D          

 26 28  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 12  3  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  2  0  0  0  0
 14  6  2  0  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19  9  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  1  0  0  0  0
 25 18  2  0  0  0  0
 26 14  1  0  0  0  0
 26 18  1  0  0  0  0
M  END
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3D MOL for NP0047582 (Grevilline D)

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3D SDF for NP0047582 (Grevilline D)

  Mrv0541 05061307002D          

 26 28  0  0  0  0            999 V2000
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   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
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  8  6  1  0  0  0  0
  9  2  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11 10  2  0  0  0  0
 12  3  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  2  0  0  0  0
 14  6  2  0  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19  9  1  0  0  0  0
 20 11  1  0  0  0  0
 21 12  1  0  0  0  0
 22 13  1  0  0  0  0
 23 16  2  0  0  0  0
 24 17  1  0  0  0  0
 25 18  2  0  0  0  0
 26 14  1  0  0  0  0
 26 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047582

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(=C(O)C=C1)C1=C(O)C(=O)O\C(=C\C2=CC(O)=C(O)C=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H12O8/c19-9-2-4-11(20)10(7-9)15-16(23)14(26-18(25)17(15)24)6-8-1-3-12(21)13(22)5-8/h1-7,19-22,24H/b14-6+

> <INCHI_KEY>
PVXXMVFQPHEMMT-MKMNVTDBSA-N

> <FORMULA>
C18H12O8

> <MOLECULAR_WEIGHT>
356.2831

> <EXACT_MASS>
356.05321736

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
33.318933189873874

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-4-(2,5-dihydroxyphenyl)-6-[(3,4-dihydroxyphenyl)methylidene]-3-hydroxy-5,6-dihydro-2H-pyran-2,5-dione

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
2.432159655333333

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.726495745158669

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.466752423396069

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8248972833703947

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
91.39259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6E)-4-(2,5-dihydroxyphenyl)-6-[(3,4-dihydroxyphenyl)methylidene]-3-hydroxypyran-2,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0047582 (Grevilline D)
Download
PDB for NP0047582 (Grevilline D)
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      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    9                                                       
CONECT    3    1   12                                                       
CONECT    4    2   11                                                       
CONECT    5    8   13                                                       
CONECT    6    8   14                                                       
CONECT    7    9   10                                                       
CONECT    8    1    5    6                                                  
CONECT    9    2    7   19                                                  
CONECT   10    7   11   15                                                  
CONECT   11    4   10   20                                                  
CONECT   12    3   13   21                                                  
CONECT   13    5   12   22                                                  
CONECT   14    6   16   26                                                  
CONECT   15   10   16   17                                                  
CONECT   16   14   15   23                                                  
CONECT   17   15   18   24                                                  
CONECT   18   17   25   26                                                  
CONECT   19    9                                                            
CONECT   20   11                                                            
CONECT   21   12                                                            
CONECT   22   13                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   18                                                            
CONECT   26   14   18                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

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3D PDB for NP0047582 (Grevilline D)
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SMILES for NP0047582 (Grevilline D)
OC1=CC(=C(O)C=C1)C1=C(O)C(=O)O\C(=C\C2=CC(O)=C(O)C=C2)C1=O
Download
INCHI for NP0047582 (Grevilline D)
InChI=1S/C18H12O8/c19-9-2-4-11(20)10(7-9)15-16(23)14(26-18(25)17(15)24)6-8-1-3-12(21)13(22)5-8/h1-7,19-22,24H/b14-6+
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View in JSmol
SynonymsNot Available
Chemical FormulaC18H12O8
Average Mass356.2831 Da
Monoisotopic Mass356.05322 Da
IUPAC Name(6E)-4-(2,5-dihydroxyphenyl)-6-[(3,4-dihydroxyphenyl)methylidene]-3-hydroxy-5,6-dihydro-2H-pyran-2,5-dione
Traditional Name(6E)-4-(2,5-dihydroxyphenyl)-6-[(3,4-dihydroxyphenyl)methylidene]-3-hydroxypyran-2,5-dione
CAS Registry Number54707-49-2
SMILES
OC1=CC(=C(O)C=C1)C1=C(O)C(=O)O\C(=C\C2=CC(O)=C(O)C=C2)C1=O
InChI Identifier
InChI=1S/C18H12O8/c19-9-2-4-11(20)10(7-9)15-16(23)14(26-18(25)17(15)24)6-8-1-3-12(21)13(22)5-8/h1-7,19-22,24H/b14-6+
InChI KeyPVXXMVFQPHEMMT-MKMNVTDBSA-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 hydroquinones. Hydroquinones are compounds containing a hydroquinone moiety, which consists of a benzene ring with a hydroxyl groups at positions 1 and 4.
KingdomOrganic compounds  
Super ClassBenzenoids  
ClassPhenols  
Sub ClassBenzenediols  
Direct ParentHydroquinones  
Alternative Parents
Substituents
  • Catechol
    • 

  • Hydroquinone
    • 

  • 1-hydroxy-4-unsubstituted benzenoid
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Dihydropyranone
    • 

  • Monocyclic benzene moiety
    • 

  • Pyran
    • 

  • Enol ester
    • 

  • Vinylogous acid
    • 

  • Alpha,beta-unsaturated carboxylic ester
    • 

  • Enoate ester
    • 

  • Carboxylic acid ester
    • 

  • Cyclic ketone
    • 

  • Ketone
    • 

  • Lactone
    • 

  • Carboxylic acid derivative
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Enol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP2.15ALOGPS
logP2.43ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.47ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity91.39 m³·mol⁻¹ChemAxon
Polarizability33.32 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033246  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011265  
KNApSAcK IDNot Available
Chemspider ID20124986  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available