NP-MRD: Showing NP-Card for Gyrocyanin (NP0047862)

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Record Information

Version

2.0

Created at

2022-03-17 20:47:10 UTC

Updated at

2022-03-17 20:47:11 UTC

NP-MRD ID

NP0047862

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gyrocyanin

Description

Gyrocyanin belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position. Gyrocyanin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Gyrocyanin has been detected, but not quantified in, mushrooms. Gyrocyanin is found in Gyroporus cyanescens . This could make gyrocyanin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307362D          

 22 24  0  0  0  0            999 V2000
    0.7429    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3014    2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9458    2.8672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3874    1.5082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5275    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0860    3.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7304    3.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1720    1.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1298    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7743    2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6991    2.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3435    2.5701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6548    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9897    1.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    2.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347    1.0206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    2.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1282    2.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3222    3.1152    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2197    0.3532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  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
  9  1  2  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  1  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 15  2  0  0  0  0
 21 16  2  0  0  0  0
 22 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047862

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O5/c18-11-5-1-9(2-6-11)13-15(20)14(17(22)16(13)21)10-3-7-12(19)8-4-10/h1-8,13,18-19,22H

> <INCHI_KEY>
DIFAFZFNMSLGGN-UHFFFAOYSA-N

> <FORMULA>
C17H12O5

> <MOLECULAR_WEIGHT>
296.2742

> <EXACT_MASS>
296.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.654936376728845

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione

> <ALOGPS_LOGP>
3.16

> <JCHEM_LOGP>
2.9530005960000003

> <ALOGPS_LOGS>
-3.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.956201687877945

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.52530307510005

> <JCHEM_PKA_STRONGEST_BASIC>
-4.403961452845587

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
80.46039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.71e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-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       1.387   2.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.563   5.352   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.499   5.352   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.323   2.815   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.851   3.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.027   5.828   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.963   5.828   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -7.788   3.291   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.242   3.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.179   3.846   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.172   4.798   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.108   4.798   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.222   3.370   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.714   3.370   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.468   4.275   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.698   1.905   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.238   1.905   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.636   5.273   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -9.573   5.273   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.468   5.815   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -0.793   0.659   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.143   0.659   0.000  0.00  0.00           O+0
CONECT    1    5    9                                                       
CONECT    2    6    9                                                       
CONECT    3    7   10                                                       
CONECT    4    8   10                                                       
CONECT    5    1   11                                                       
CONECT    6    2   11                                                       
CONECT    7    3   12                                                       
CONECT    8    4   12                                                       
CONECT    9    1    2   13                                                  
CONECT   10    3    4   14                                                  
CONECT   11    5    6   18                                                  
CONECT   12    7    8   19                                                  
CONECT   13    9   15   16                                                  
CONECT   14   10   15   17                                                  
CONECT   15   13   14   20                                                  
CONECT   16   13   17   21                                                  
CONECT   17   14   16   22                                                  
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
3,5-Bis(4-hydroxyphenyl)-1,2,4-cyclopentanetrione	HMDB
4-Hydroxy-2,5-bis(4-hydroxyphenyl)-4-cyclopentene-1,3-dione, 9ci	HMDB

Chemical Formula

C₁₇H₁₂O₅

Average Mass

296.2742 Da

Monoisotopic Mass

296.06847 Da

IUPAC Name

4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione

Traditional Name

4-hydroxy-2,5-bis(4-hydroxyphenyl)cyclopent-4-ene-1,3-dione

CAS Registry Number

52591-12-5

SMILES

OC1=C(C(=O)C(C1=O)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H12O5/c18-11-5-1-9(2-6-11)13-15(20)14(17(22)16(13)21)10-3-7-12(19)8-4-10/h1-8,13,18-19,22H

InChI Key

DIFAFZFNMSLGGN-UHFFFAOYSA-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...
Gyroporus cyanescens	-	KNApSAcK
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 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
1,3-diketone
1,3-dicarbonyl compound
Monocyclic benzene moiety
Vinylogous acid
Cyclic ketone
Ketone
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.16	ALOGPS
logP	2.95	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.53	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.46 m³·mol⁻¹	ChemAxon
Polarizability	29.65 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

HMDB0034126

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012399

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

71438153

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gyrocyanin (NP0047862)

MOL for NP0047862 (Gyrocyanin)

3D MOL for NP0047862 (Gyrocyanin)

3D SDF for NP0047862 (Gyrocyanin)

3D-SDF for NP0047862 (Gyrocyanin)

PDB for NP0047862 (Gyrocyanin)

3D PDB for NP0047862 (Gyrocyanin)

SMILES for NP0047862 (Gyrocyanin)

INCHI for NP0047862 (Gyrocyanin)

Structure for NP0047862 (Gyrocyanin)

3D Structure for NP0047862 (Gyrocyanin)