NP-MRD: Showing NP-Card for 4,5,7-trihydroxynaphthalene-1,2-dione (NP0160331)

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Record Information

Version

2.0

Created at

2022-09-02 18:15:39 UTC

Updated at

2022-09-02 18:15:40 UTC

NP-MRD ID

NP0160331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,7-trihydroxynaphthalene-1,2-dione

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). 4,5,7-trihydroxynaphthalene-1,2-dione is found in Leptosphaeria maculans, Streptomyces coelicolor, Streptomyces griseus, Streptomyces venezuelae and Verticillium dahliae. 4,5,7-trihydroxynaphthalene-1,2-dione was first documented in 2020 (PMID: 33363524). Based on a literature review a small amount of articles have been published on Flaviolin (PMID: 35293722) (PMID: 34601869) (PMID: 33921255) (PMID: 33706119).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022220152D          

 15 16  0  0  0  0            999 V2000
    0.0000   -1.6500    0.0000 O   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
    0.7145   -0.4125    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
    1.4289    0.8250    0.0000 O   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
    2.8579    0.8250    0.0000 O   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   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   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0160331

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
XNPCAGMCQDGQKK-UHFFFAOYSA-N

> <FORMULA>
C10H6O5

> <MOLECULAR_WEIGHT>
206.153

> <EXACT_MASS>
206.021523293

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.24262563844386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
0.8456216183333333

> <ALOGPS_LOGS>
-1.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.57186428761166

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.786930290727469

> <JCHEM_PKA_STRONGEST_BASIC>
-5.481359631821207

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
52.0191

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.26e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5,7-trihydroxynaphthalene-1,2-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13    2   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₆O₅

Average Mass

206.1530 Da

Monoisotopic Mass

206.02152 Da

IUPAC Name

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

Traditional Name

4,5,7-trihydroxynaphthalene-1,2-dione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

XNPCAGMCQDGQKK-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
Leptosphaeria maculans	LOTUS Database	35616633
Streptomyces coelicolor	LOTUS Database	35616633
Streptomyces griseus	LOTUS Database	35616633
Streptomyces venezuelae	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
1-naphthol
Quinone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Vinylogous acid
Cyclic ketone
Ketone
Polyol
Enol
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	1.29	ALOGPS
logP	0.85	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.79	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.02 m³·mol⁻¹	ChemAxon
Polarizability	18.24 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

C00049122

Chemspider ID

141022

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

160478

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Noguchi T, Isogai S, Terada T, Nishiyama M, Kuzuyama T: Cryptic Oxidative Transamination of Hydroxynaphthoquinone in Natural Product Biosynthesis. J Am Chem Soc. 2022 Mar 30;144(12):5435-5440. doi: 10.1021/jacs.1c13074. Epub 2022 Mar 16. [PubMed:35293722 ]
He H, Tang J, Chen J, Hu J, Zhu Z, Liu Y, Shuai L, Cao L, Liu Z, Xia Z, Ding X, Hu S, Zhang Y, Rang J, Xia L: Flaviolin-Like Gene Cluster Deletion Optimized the Butenyl-Spinosyn Biosynthesis Route in Saccharopolyspora pogona. ACS Synth Biol. 2021 Oct 15;10(10):2740-2752. doi: 10.1021/acssynbio.1c00344. Epub 2021 Oct 3. [PubMed:34601869 ]
Oh JJ, Kim YJ, Kim JY, Kwon SL, Lee C, Lee ME, Kim JW, Kim GH: Genomic Analysis and Assessment of Melanin Synthesis in Amorphotheca resinae KUC3009. J Fungi (Basel). 2021 Apr 12;7(4):289. doi: 10.3390/jof7040289. [PubMed:33921255 ]
Wang B, Li X, Tabudravu J, Wang S, Deng H, Pan L: The chemical profile of activated secondary metabolites by overexpressing LaeA in Aspergillus niger. Microbiol Res. 2021 Jul;248:126735. doi: 10.1016/j.micres.2021.126735. Epub 2021 Mar 3. [PubMed:33706119 ]
Lu J, Long Q, Zhao Z, Chen L, He W, Hong J, Liu K, Wang Y, Pang X, Deng Z, Tao M: Engineering the Erythromycin-Producing Strain Saccharopolyspora erythraea HOE107 for the Heterologous Production of Polyketide Antibiotics. Front Microbiol. 2020 Dec 8;11:593217. doi: 10.3389/fmicb.2020.593217. eCollection 2020. [PubMed:33363524 ]
LOTUS database [Link]

Showing NP-Card for 4,5,7-trihydroxynaphthalene-1,2-dione (NP0160331)

MOL for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

3D MOL for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

3D SDF for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

3D-SDF for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

PDB for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

3D PDB for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

SMILES for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

INCHI for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

Structure for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)

3D Structure for NP0160331 (4,5,7-trihydroxynaphthalene-1,2-dione)