NP-MRD: Showing NP-Card for 7-Chlorocanarione (NP0008793)

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Record Information

Version

2.0

Created at

2020-12-09 06:17:47 UTC

Updated at

2021-07-15 17:01:25 UTC

NP-MRD ID

NP0008793

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Chlorocanarione

Provided By

NPAtlas

Description

7-Chlorocanarione is found in Lethariella sernanderi. 7-Chlorocanarione was first documented in 2010 (PMID: 19802654). Based on a literature review very few articles have been published on 7-chloro-5,8-dihydroxy-2-methyl-4H,6H,9H-cyclohexa[g]chromene-4,6,9-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

 28 30  0  0  0  0            999 V2000
   -4.5446    0.8381    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2576    0.4079    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239   -0.3900   -0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1621   -0.8354   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -1.5547   -2.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.4256   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -0.8128   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3089   -1.6005   -2.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -0.4078   -0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249    0.3860    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320    0.7812    1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    0.3761    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081    0.7688    1.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7348    0.7854    1.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7464    1.5115    2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9755    0.3299    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063    0.7142    0.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937   -0.4395   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251   -0.9375   -1.3247 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -0.8506   -1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7227   -1.5805   -2.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4774    1.9205    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068    0.2748    2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3737    0.7730    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736   -0.7049   -0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350   -1.9981   -2.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2397    1.4090    1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008    1.2612    1.8241 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  2  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13  2  1  0  0  0  0
 12  6  1  0  0  0  0
 20  9  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
  8 26  1  0  0  0  0
 11 27  1  0  0  0  0
 17 28  1  0  0  0  0
M  END


  Mrv1652306242106303D          

 28 30  0  0  0  0            999 V2000
   -4.5446    0.8381    1.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2576    0.4079    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3239   -0.3900   -0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1621   -0.8354   -1.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2430   -1.5547   -2.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.4256   -0.5884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2455   -0.8128   -1.1338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3089   -1.6005   -2.2357 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732   -0.4078   -0.5711 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4249    0.3860    0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2320    0.7812    1.0958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9721    0.3761    0.5329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1081    0.7688    1.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7348    0.7854    1.0938 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7464    1.5115    2.1094 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9755    0.3299    0.4528 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2063    0.7142    0.9865 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937   -0.4395   -0.6234 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251   -0.9375   -1.3247 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -0.8506   -1.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7227   -1.5805   -2.2153 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4774    1.9205    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8068    0.2748    2.0965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3737    0.7730    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2736   -0.7049   -0.9687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3350   -1.9981   -2.7899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2397    1.4090    1.9739 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3008    1.2612    1.8241 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  2  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
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 13  2  1  0  0  0  0
 12  6  1  0  0  0  0
 20  9  1  0  0  0  0
  1 22  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  3 25  1  0  0  0  0
  8 26  1  0  0  0  0
 11 27  1  0  0  0  0
 17 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008793

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(Cl)C(=O)C2=C(C([H])=C3OC(=C([H])C(=O)C3=C2O[H])C([H])([H])[H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H7ClO6/c1-4-2-6(16)9-7(21-4)3-5-8(12(9)18)13(19)10(15)14(20)11(5)17/h2-3,18,20H,1H3

> <INCHI_KEY>
FLJHYFOGNCKUDJ-UHFFFAOYSA-N

> <FORMULA>
C14H7ClO6

> <MOLECULAR_WEIGHT>
306.65

> <EXACT_MASS>
305.9931156

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
27.95376240020041

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-chloro-5,8-dihydroxy-2-methyl-4H,6H,9H-cyclohexa[g]chromene-4,6,9-trione

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.2593547176666666

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
6.384537811852688

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.939233677536168

> <JCHEM_PKA_STRONGEST_BASIC>
-5.355475948735313

> <JCHEM_POLAR_SURFACE_AREA>
100.9

> <JCHEM_REFRACTIVITY>
75.97199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.86e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-chloro-5,8-dihydroxy-2-methylcyclohexa[g]chromene-4,6,9-trione

> <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      -4.545   0.838   1.190  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.258   0.408   0.585  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.324  -0.390  -0.531  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.162  -0.835  -1.158  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.243  -1.555  -2.164  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.959  -0.426  -0.588  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.246  -0.813  -1.134  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.309  -1.601  -2.236  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.473  -0.408  -0.571  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.425   0.386   0.539  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.232   0.781   1.096  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.972   0.376   0.533  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.108   0.769   1.086  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.735   0.785   1.094  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.746   1.512   2.109  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.975   0.330   0.453  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.206   0.714   0.987  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.994  -0.440  -0.623  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       5.525  -0.938  -1.325  0.00  0.00          Cl+0
HETATM   20  C   UNK     0       2.707  -0.851  -1.194  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.723  -1.581  -2.215  0.00  0.00           O+0
HETATM   22  H   UNK     0      -4.477   1.921   1.479  0.00  0.00           H+0
HETATM   23  H   UNK     0      -4.807   0.275   2.096  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.374   0.773   0.454  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.274  -0.705  -0.969  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.335  -1.998  -2.790  0.00  0.00           H+0
HETATM   27  H   UNK     0       0.240   1.409   1.974  0.00  0.00           H+0
HETATM   28  H   UNK     0       5.301   1.261   1.824  0.00  0.00           H+0
CONECT    1    2   22   23   24                                             
CONECT    2    1    3   13                                                  
CONECT    3    2    4   25                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   26                                                       
CONECT    9    7   10   20                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   27                                                  
CONECT   12   11   13    6                                                  
CONECT   13   12    2                                                       
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   28                                                       
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21    9                                                  
CONECT   21   20                                                            
CONECT   22    1                                                            
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    3                                                            
CONECT   26    8                                                            
CONECT   27   11                                                            
CONECT   28   17                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₄H₇ClO₆

Average Mass

306.6500 Da

Monoisotopic Mass

305.99312 Da

IUPAC Name

7-chloro-5,8-dihydroxy-2-methyl-4H,6H,9H-cyclohexa[g]chromene-4,6,9-trione

Traditional Name

7-chloro-5,8-dihydroxy-2-methylcyclohexa[g]chromene-4,6,9-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C2=C(O1)C=C1C(=O)C(O)=C(Cl)C(=O)C1=C2O

InChI Identifier

InChI=1S/C14H7ClO6/c1-4-2-6(16)9-7(21-4)3-5-8(12(9)18)13(19)10(15)14(20)11(5)17/h2-3,18,20H,1H3

InChI Key

FLJHYFOGNCKUDJ-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
Lethariella sernanderi	NPAtlas	19802654

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Naphthoquinone
Chromone
Benzopyran
Naphthalene
1-benzopyran
Quinone
Aryl ketone
Pyranone
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Pyran
Heteroaromatic compound
Alpha-chloroketone
Alpha-haloketone
Vinylogous acid
Vinylogous halide
Ketone
Oxacycle
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organic oxide
Organic oxygen compound
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.16	ALOGPS
logP	2.26	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	100.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	75.97 m³·mol⁻¹	ChemAxon
Polarizability	27.95 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

NPAtlas ID

NPA006214

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78435951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kinoshita K, Togawa T, Hiraishi A, Nakajima Y, Koyama K, Narui T, Wang LS, Takahashi K: Antioxidant activity of red pigments from the lichens Lethariella sernanderi, L. cashmeriana, and L. sinensis. J Nat Med. 2010 Jan;64(1):85-8. doi: 10.1007/s11418-009-0364-2. Epub 2009 Oct 3. [PubMed:19802654 ]

Showing NP-Card for 7-Chlorocanarione (NP0008793)

MOL for NP0008793 (7-Chlorocanarione)

3D MOL for NP0008793 (7-Chlorocanarione)

3D SDF for NP0008793 (7-Chlorocanarione)

3D-SDF for NP0008793 (7-Chlorocanarione)

PDB for NP0008793 (7-Chlorocanarione)

3D PDB for NP0008793 (7-Chlorocanarione)

SMILES for NP0008793 (7-Chlorocanarione)

INCHI for NP0008793 (7-Chlorocanarione)

Structure for NP0008793 (7-Chlorocanarione)

3D Structure for NP0008793 (7-Chlorocanarione)