NP-MRD: Showing NP-Card for Purpurogallin (NP0051737)

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Record Information

Version

1.0

Created at

2022-04-27 22:59:24 UTC

Updated at

2022-04-27 22:59:24 UTC

NP-MRD ID

NP0051737

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpurogallin

Description

Purpurogallin belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2. Purpurogallin is a moderately basic compound (based on its pKa). Purpurogallin is found in Dryophanta divisa and Quercus pedunculanta. It was first documented in 1948 (PMID: 18878807). A cyclic ketone that is 5H-benzocycloheptene bearing an oxo group at position 5 and hydroxy groups at positions 2, 3, 4 and 6 (PMID: 1799443) (PMID: 8326817) (PMID: 9178568) (PMID: 9568088).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05041412042D          

 16 17  0  0  0  0            999 V2000
    4.4358    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -1.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315   -1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9502   -1.6575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -2.0003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -1.9191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  2  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  9  2  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051737

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C(O)=C2C(=C1)C=CC=C(O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)

> <INCHI_KEY>
WDGFFVCWBZVLCE-UHFFFAOYSA-N

> <FORMULA>
C11H8O5

> <MOLECULAR_WEIGHT>
220.1782

> <EXACT_MASS>
220.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
20.49454197065156

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one

> <ALOGPS_LOGP>
1.27

> <JCHEM_LOGP>
1.936774853333333

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.860315926415606

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.794419173300208

> <JCHEM_PKA_STRONGEST_BASIC>
2.9442146725801446

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
59.047700000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
purpurogallin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    5    7                                                       
CONECT    5    2    4    8                                                  
CONECT    6    3    9   12                                                  
CONECT    7    4   10   13                                                  
CONECT    8    5    9   11                                                  
CONECT    9    6    8   14                                                  
CONECT   10    7   11   15                                                  
CONECT   11    8   10   16                                                  
CONECT   12    6                                                            
CONECT   13    7                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
2,3,4,6-Tetrahydroxy-5H-benzocycloheptene-5-one	ChEBI
2,3,4,6-Tetrahydroxybenzocyclohepten-5-one	ChEBI
Purpurogalline	ChEBI

Chemical Formula

C₁₁H₈O₅

Average Mass

220.1782 Da

Monoisotopic Mass

220.03717 Da

IUPAC Name

2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one

Traditional Name

purpurogallin

CAS Registry Number

Not Available

SMILES

OC1=C(O)C(O)=C2C(=C1)C=CC=C(O)C2=O

InChI Identifier

InChI=1S/C11H8O5/c12-6-3-1-2-5-4-7(13)10(15)11(16)8(5)9(6)14/h1-4,13,15-16H,(H,12,14)

InChI Key

WDGFFVCWBZVLCE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Dryophanta divisa	-	KNApSAcK
Quercus pedunculanta	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropolones. Tropolones are compounds containing tropone ring with a hydroxyl group at ring position 2.

Kingdom

Organic compounds

Super Class

Hydrocarbon derivatives

Class

Tropones

Sub Class

Tropolones

Direct Parent

Tropolones

Alternative Parents

Substituents

Tropolone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Cyclic ketone
Polyol
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:8647 )
phenols (CHEBI:8647 )
tetrol (CHEBI:8647 )

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	1.27	ALOGPS
logP	1.94	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	6.79	ChemAxon
pKa (Strongest Basic)	2.94	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	59.05 m³·mol⁻¹	ChemAxon
Polarizability	20.49 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003013

Chemspider ID

Not Available

KEGG Compound ID

C09964

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Purpurogallin

METLIN ID

Not Available

PubChem Compound

5281571

PDB ID

Not Available

ChEBI ID

8647

Good Scents ID

Not Available

References

General References

Wu TW, Zeng LH, Wu J, Carey D: Purpurogallin--a natural and effective hepatoprotector in vitro and in vivo. Biochem Cell Biol. 1991 Oct-Nov;69(10-11):747-50. doi: 10.1139/o91-113. [PubMed:1799443 ]
HAWORTH RD, MOORE BP, PAUSON PL: Purpurogallin. J Chem Soc. 1948 Jul;1:1045-51. [PubMed:18878807 ]
Sugiyama H, Fung KP, Wu TW: Purpurogallin as an antioxidant protector of human erythrocytes against lysis by peroxyl radicals. Life Sci. 1993;53(4):PL39-43. doi: 10.1016/0024-3205(93)90759-v. [PubMed:8326817 ]
Inamori Y, Muro C, Sajima E, Katagiri M, Okamoto Y, Tanaka H, Sakagami Y, Tsujibo H: Biological activity of purpurogallin. Biosci Biotechnol Biochem. 1997 May;61(5):890-2. doi: 10.1271/bbb.61.890. [PubMed:9178568 ]
Sheu SY, Lai CH, Chiang HC: Inhibition of xanthine oxidase by purpurogallin and silymarin group. Anticancer Res. 1998 Jan-Feb;18(1A):263-7. [PubMed:9568088 ]

Showing NP-Card for Purpurogallin (NP0051737)

MOL for NP0051737 (Purpurogallin)

3D MOL for NP0051737 (Purpurogallin)

3D SDF for NP0051737 (Purpurogallin)

3D-SDF for NP0051737 (Purpurogallin)

PDB for NP0051737 (Purpurogallin)

3D PDB for NP0051737 (Purpurogallin)

SMILES for NP0051737 (Purpurogallin)

INCHI for NP0051737 (Purpurogallin)

Structure for NP0051737 (Purpurogallin)

3D Structure for NP0051737 (Purpurogallin)