NP-MRD: Showing NP-Card for Methylspinazarin (NP0021454)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-01-06 06:42:52 UTC

Updated at

2021-07-15 17:36:24 UTC

NP-MRD ID

NP0021454

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methylspinazarin

Provided By

NPAtlas

Description

Methylspinazarin is found in Streptomyces filipinensis and Streptomyces sp.. Methylspinazarin was first documented in 1973 (PMID: 4781283). Based on a literature review very few articles have been published on 2,3,5,8-tetrahydroxy-6-methyl-1,4-dihydronaphthalene-1,4-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105153D          

 25 26  0  0  0  0            999 V2000
   -3.6004   -0.0246   -0.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1507   -0.3224   -0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6368   -1.6018   -0.2270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2763   -1.8509   -0.1567 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322   -3.1336   -0.1355 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6108   -0.7941   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0842    0.4873   -0.1277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779    0.7296   -0.1981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6960    2.0540   -0.2144 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0409    1.5866   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    2.7671   -0.0923 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4815    1.3918    0.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3612    2.4908    0.0530 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9324    0.1427    0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3126   -0.0606    0.0919 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0588   -1.0043   -0.0305 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5016   -2.2014   -0.0124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8447    0.8048    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8237    0.3526   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1969   -0.9299   -0.1006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3101   -2.4477   -0.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4126   -3.9012   -0.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6554    2.3395   -0.2635 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0003    3.3693    0.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6947   -0.2438    1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  8  2  1  0  0  0  0
 16  6  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
  3 21  1  0  0  0  0
  5 22  1  0  0  0  0
  9 23  1  0  0  0  0
 13 24  1  0  0  0  0
 15 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021454

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C(O[H])=C(O[H])C(=O)C2=C(O[H])C(=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C11H8O6/c1-3-2-4(12)5-6(7(3)13)9(15)11(17)10(16)8(5)14/h2,12-13,16-17H,1H3

> <INCHI_KEY>
WXLPYHMWBMMBOS-UHFFFAOYSA-N

> <FORMULA>
C11H8O6

> <MOLECULAR_WEIGHT>
236.179

> <EXACT_MASS>
236.032087978

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
21.561535190881287

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,5,8-tetrahydroxy-6-methyl-1,4-dihydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
1.6632933340000002

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.458733537572186

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.267012864108869

> <JCHEM_PKA_STRONGEST_BASIC>
-5.722321408066514

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
59.12100000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,5,8-tetrahydroxy-6-methylnaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.600  -0.025  -0.323  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.151  -0.322  -0.249  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.637  -1.602  -0.227  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.276  -1.851  -0.157  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.232  -3.134  -0.136  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.611  -0.794  -0.106  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.084   0.487  -0.128  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.278   0.730  -0.198  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.696   2.054  -0.214  0.00  0.00           O+0
HETATM   10  C   UNK     0       1.041   1.587  -0.073  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.570   2.767  -0.092  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.482   1.392   0.002  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.361   2.491   0.053  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.932   0.143   0.020  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.313  -0.061   0.092  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.059  -1.004  -0.031  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.502  -2.201  -0.012  0.00  0.00           O+0
HETATM   18  H   UNK     0      -3.845   0.805   0.373  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.824   0.353  -1.363  0.00  0.00           H+0
HETATM   20  H   UNK     0      -4.197  -0.930  -0.101  0.00  0.00           H+0
HETATM   21  H   UNK     0      -2.310  -2.448  -0.266  0.00  0.00           H+0
HETATM   22  H   UNK     0      -0.413  -3.901  -0.173  0.00  0.00           H+0
HETATM   23  H   UNK     0      -2.655   2.340  -0.264  0.00  0.00           H+0
HETATM   24  H   UNK     0       3.000   3.369   0.403  0.00  0.00           H+0
HETATM   25  H   UNK     0       4.695  -0.244   1.006  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    1    3    8                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4   22                                                       
CONECT    6    4    7   16                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9    2                                                  
CONECT    9    8   23                                                       
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12   24                                                       
CONECT   14   12   15   16                                                  
CONECT   15   14   25                                                       
CONECT   16   14   17    6                                                  
CONECT   17   16                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    3                                                            
CONECT   22    5                                                            
CONECT   23    9                                                            
CONECT   24   13                                                            
CONECT   25   15                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   52    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
2,3,5,8-Tetrahydroxy-6-methyl-1,4-naphthoquinone	MeSH

Chemical Formula

C₁₁H₈O₆

Average Mass

236.1790 Da

Monoisotopic Mass

236.03209 Da

IUPAC Name

2,3,5,8-tetrahydroxy-6-methyl-1,4-dihydronaphthalene-1,4-dione

Traditional Name

2,3,5,8-tetrahydroxy-6-methylnaphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)C(O)=C(O)C(=O)C2=C1O

InChI Identifier

InChI=1S/C11H8O6/c1-3-2-4(12)5-6(7(3)13)9(15)11(17)10(16)8(5)14/h2,12-13,16-17H,1H3

InChI Key

WXLPYHMWBMMBOS-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
Streptomyces filipinensis	LOTUS Database	35616633
Streptomyces sp.	NPAtlas	4781283

Species Where Detected

Species Name	Source	Reference
Streptomyces filipinensis MD 157-A9	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthoquinones. These 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-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Ketone
Enediol
Polyol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	0.36	ALOGPS
logP	1.66	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.27	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	59.12 m³·mol⁻¹	ChemAxon
Polarizability	21.56 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

NPAtlas ID

NPA000102

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00018861

Chemspider ID

19960855

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

135483447

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chimura H, Sawa T, Takita T, Matsuzaki M, Takeuchi T: Letter: Methylspinazarin and dihydromethylspinazarin, catechol-O-methyl transferase inhibitors produced by Streptomyces. J Antibiot (Tokyo). 1973 Feb;26(2):112-4. doi: 10.7164/antibiotics.26.112. [PubMed:4781283 ]

Showing NP-Card for Methylspinazarin (NP0021454)

MOL for NP0021454 (Methylspinazarin)

3D MOL for NP0021454 (Methylspinazarin)

3D SDF for NP0021454 (Methylspinazarin)

3D-SDF for NP0021454 (Methylspinazarin)

PDB for NP0021454 (Methylspinazarin)

3D PDB for NP0021454 (Methylspinazarin)

SMILES for NP0021454 (Methylspinazarin)

INCHI for NP0021454 (Methylspinazarin)

Structure for NP0021454 (Methylspinazarin)

3D Structure for NP0021454 (Methylspinazarin)