NP-MRD: Showing NP-Card for 2,5,7-trihydroxynaphthoquinone (NP0168847)

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Record Information

Version

2.0

Created at

2022-09-03 04:42:44 UTC

Updated at

2022-09-03 04:42:44 UTC

NP-MRD ID

NP0168847

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,5,7-trihydroxynaphthoquinone

Description

Flaviolin belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Flaviolin is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,5,7-trihydroxynaphthoquinone is found in Aspergillus oryzae, Monosporascus cannonballus and Verticillium dahliae. 2,5,7-trihydroxynaphthoquinone was first documented in 2010 (PMID: 20351110). A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone having three hydroxy substituents placed at the 2-, 5- and 7-positions.

Structure

MOL 3D MOL SDF PDB SMILES InChI

FLV
  Mrv0541 02231216152D          

 15 16  0  0  0  0            999 V2000
   -0.7393    1.6497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6896    0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1186    0.8247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4041   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6896   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6896   -1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0248   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393   -0.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7393   -1.6503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538   -0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4538    0.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1683    0.8247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 14  1  0  0  0  0
  3  4  1  0  0  0  0
  3 10  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0168847

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C(O)=C1)C(=O)C=C(O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H6O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-3,11-12,14H

> <INCHI_KEY>
RROPNRTUMVVUED-UHFFFAOYSA-N

> <FORMULA>
C10H6O5

> <MOLECULAR_WEIGHT>
206.1516

> <EXACT_MASS>
206.021523302

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
18.308030026330528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,7-trihydroxy-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.0185296259999999

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.5555686706994

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.116416527308647

> <JCHEM_PKA_STRONGEST_BASIC>
-4.453885671783742

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
52.1124

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flaviolin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: FLV                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.380   3.079   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.380   1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.046   0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.287   1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.621   0.769   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.955   1.539   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.621  -0.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.287  -1.541   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.287  -3.081   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -0.046  -0.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.380  -1.541   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.380  -3.081   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.714  -0.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.714   0.769   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.047   1.539   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    3    8   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14    2   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
2,5,7-Trihydroxy-1,4-naphthalenedione	ChEBI
4,5,7-Trihydroxynaphthalene-1,2-dione	ChEBI

Chemical Formula

C₁₀H₆O₅

Average Mass

206.1516 Da

Monoisotopic Mass

206.02152 Da

IUPAC Name

2,5,7-trihydroxy-1,4-dihydronaphthalene-1,4-dione

Traditional Name

flaviolin

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C(O)=C1)C(=O)C=C(O)C2=O

InChI Identifier

InChI=1S/C10H6O5/c11-4-1-5-9(6(12)2-4)7(13)3-8(14)10(5)15/h1-3,11-12,14H

InChI Key

RROPNRTUMVVUED-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aspergillus oryzae	LOTUS Database	35616633
Monosporascus cannonballus	LOTUS Database	35616633
Verticillium dahliae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Vinylogous acid
Ketone
Polyol
Enol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthoquinone (CHEBI:42646 )

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	1.33	ALOGPS
logP	1.02	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.5	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	0	ChemAxon
Refractivity	52.11 m³·mol⁻¹	ChemAxon
Polarizability	18.31 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

DB02521

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C18012

BioCyc ID

CPD-10679

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

42646

Good Scents ID

Not Available

References

General References

Haug-Schifferdecker E, Arican D, Bruckner R, Heide L: A new group of aromatic prenyltransferases in fungi, catalyzing a 2,7-dihydroxynaphthalene 3-dimethylallyl-transferase reaction. J Biol Chem. 2010 May 28;285(22):16487-94. doi: 10.1074/jbc.M110.113720. Epub 2010 Mar 29. [PubMed:20351110 ]
LOTUS database [Link]

Showing NP-Card for 2,5,7-trihydroxynaphthoquinone (NP0168847)

MOL for NP0168847 (2,5,7-trihydroxynaphthoquinone)

3D MOL for NP0168847 (2,5,7-trihydroxynaphthoquinone)

3D SDF for NP0168847 (2,5,7-trihydroxynaphthoquinone)

3D-SDF for NP0168847 (2,5,7-trihydroxynaphthoquinone)

PDB for NP0168847 (2,5,7-trihydroxynaphthoquinone)

3D PDB for NP0168847 (2,5,7-trihydroxynaphthoquinone)

SMILES for NP0168847 (2,5,7-trihydroxynaphthoquinone)

INCHI for NP0168847 (2,5,7-trihydroxynaphthoquinone)

Structure for NP0168847 (2,5,7-trihydroxynaphthoquinone)

3D Structure for NP0168847 (2,5,7-trihydroxynaphthoquinone)