NP-MRD: Showing NP-Card for Grevilline C (NP0047583)

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Record Information

Version

2.0

Created at

2022-03-17 20:42:34 UTC

Updated at

2022-03-17 20:42:34 UTC

NP-MRD ID

NP0047583

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Grevilline C

Description

Grevilline C belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Grevilline C is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Grevilline C has been detected, but not quantified in, mushrooms. This could make grevilline C a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307002D          

 26 28  0  0  0  0            999 V2000
    5.7158   -4.1250    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
    6.4302   -3.7125    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
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    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
    5.0013   -3.7125    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
    6.4302   -2.8875    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
    5.7158   -2.4750    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -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
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  2  0  0  0  0
 15  9  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 10  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


  Mrv0541 05061307002D          

 26 28  0  0  0  0            999 V2000
    5.7158   -4.1250    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
    6.4302   -3.7125    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
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    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
    5.0013   -3.7125    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
    6.4302   -2.8875    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
    5.7158   -2.4750    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
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -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
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  2  0  0  0  0
 15  9  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 10  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>
NP0047583

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
TXXYFFLNPXAMTR-MKMNVTDBSA-N

> <FORMULA>
C18H12O8

> <MOLECULAR_WEIGHT>
356.2831

> <EXACT_MASS>
356.05321736

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
33.49566640867108

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
2.432159655333333

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.637051083291542

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.665938449156294

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7162767532064906

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
91.39259999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.56e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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      10.669  -7.700   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      12.003  -6.930   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       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002  -7.700   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       9.336  -6.930   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      12.003  -5.390   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      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      13.337  -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      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    9                                                       
CONECT    3    1   10                                                       
CONECT    4    2   11                                                       
CONECT    5    8   12                                                       
CONECT    6    8   14                                                       
CONECT    7    9   13                                                       
CONECT    8    1    5    6                                                  
CONECT    9    2    7   15                                                  
CONECT   10    3   12   19                                                  
CONECT   11    4   13   20                                                  
CONECT   12    5   10   21                                                  
CONECT   13    7   11   22                                                  
CONECT   14    6   16   26                                                  
CONECT   15    9   16   17                                                  
CONECT   16   14   15   23                                                  
CONECT   17   15   18   24                                                  
CONECT   18   17   25   26                                                  
CONECT   19   10                                                            
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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₂O₈

Average Mass

356.2831 Da

Monoisotopic Mass

356.05322 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

41744-34-7

SMILES

OC1=C(O)C=C(\C=C2\OC(=O)C(O)=C(C2=O)C2=CC(O)=C(O)C=C2)C=C1

InChI Identifier

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

InChI Key

TXXYFFLNPXAMTR-MKMNVTDBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Pleurotus ostreatus	FooDB	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 catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.18	ALOGPS
logP	2.43	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.67	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.39 m³·mol⁻¹	ChemAxon
Polarizability	33.5 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033250

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011270

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Grevilline C (NP0047583)

MOL for NP0047583 (Grevilline C)

3D MOL for NP0047583 (Grevilline C)

3D SDF for NP0047583 (Grevilline C)

3D-SDF for NP0047583 (Grevilline C)

PDB for NP0047583 (Grevilline C)

3D PDB for NP0047583 (Grevilline C)

SMILES for NP0047583 (Grevilline C)

INCHI for NP0047583 (Grevilline C)

Structure for NP0047583 (Grevilline C)

3D Structure for NP0047583 (Grevilline C)