NP-MRD: Showing NP-Card for Chlorogentisylquinone (NP0003990)

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Record Information

Version

1.0

Created at

2020-12-09 01:31:07 UTC

Updated at

2021-07-15 16:47:56 UTC

NP-MRD ID

NP0003990

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chlorogentisylquinone

Provided By

NPAtlas

Description

2-Chloro-6-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively. Chlorogentisylquinone is found in Unknown-fungus sp. It was first documented in 2001 (PMID: 11827029). Based on a literature review very few articles have been published on 2-chloro-6-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118033D          

 16 16  0  0  0  0            999 V2000
   -2.5305   -1.9368    0.6806 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554   -1.0061    0.3454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2917    0.3050    0.0046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591    1.2709   -0.3455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0779    2.8524   -0.7589 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0130    0.9915   -0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973    1.9112   -0.7151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5441   -0.3116   -0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0226   -0.5673   -0.0875 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5970    0.3412    0.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3004   -1.2685    0.3049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3495    0.5220    0.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2573   -1.5693    0.3112 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4496   -0.4152   -1.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9996    1.1144    0.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1100   -2.2337    0.5546 H   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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  2  0  0  0  0
 11  2  1  0  0  0  0
  3 12  1  0  0  0  0
  9 13  1  0  0  0  0
  9 14  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003990

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])C(=O)C([H])=C(Cl)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H5ClO3/c8-6-2-5(10)1-4(3-9)7(6)11/h1-2,9H,3H2

> <INCHI_KEY>
AGIRBSHCJNCQAK-UHFFFAOYSA-N

> <FORMULA>
C7H5ClO3

> <MOLECULAR_WEIGHT>
172.56

> <EXACT_MASS>
171.9927217

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
15.020616842140535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-chloro-6-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
0.46

> <JCHEM_LOGP>
0.5278454606666667

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.910934437673461

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8377572769616277

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
41.951899999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-chloro-6-(hydroxymethyl)cyclohexa-2,5-diene-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  O   UNK     0      -2.531  -1.937   0.681  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.755  -1.006   0.345  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.292   0.305   0.005  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.459   1.271  -0.346  0.00  0.00           C+0
HETATM    5 Cl   UNK     0      -2.078   2.852  -0.759  0.00  0.00          Cl+0
HETATM    6  C   UNK     0      -0.013   0.992  -0.380  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.797   1.911  -0.715  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.544  -0.312  -0.044  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.023  -0.567  -0.088  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.597   0.341   0.833  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.300  -1.268   0.305  0.00  0.00           C+0
HETATM   12  H   UNK     0      -3.349   0.522   0.026  0.00  0.00           H+0
HETATM   13  H   UNK     0       2.257  -1.569   0.311  0.00  0.00           H+0
HETATM   14  H   UNK     0       2.450  -0.415  -1.078  0.00  0.00           H+0
HETATM   15  H   UNK     0       3.000   1.114   0.349  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.110  -2.234   0.555  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   11                                                  
CONECT    9    8   10   13   14                                             
CONECT   10    9   15                                                       
CONECT   11    8    2   16                                                  
CONECT   12    3                                                            
CONECT   13    9                                                            
CONECT   14    9                                                            
CONECT   15   10                                                            
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₇H₅ClO₃

Average Mass

172.5600 Da

Monoisotopic Mass

171.99272 Da

IUPAC Name

2-chloro-6-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione

Traditional Name

2-chloro-6-(hydroxymethyl)cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

OCC1=CC(=O)C=C(Cl)C1=O

InChI Identifier

InChI=1S/C7H5ClO3/c8-6-2-5(10)1-4(3-9)7(6)11/h1-2,9H,3H2

InChI Key

AGIRBSHCJNCQAK-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
Unknown-fungus sp.	NPAtlas	11827029

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Alpha-haloketone
Alpha-chloroketone
Vinylogous halide
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organochloride
Organohalogen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	0.46	ALOGPS
logP	0.53	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	41.95 m³·mol⁻¹	ChemAxon
Polarizability	15.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA012570

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7969740

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9793973

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Uchida R, Tomoda H, Arai M, Omura S: Chlorogentisylquinone, a new neutral sphingomyelinase inhibitor, produced by a marine fungus. J Antibiot (Tokyo). 2001 Nov;54(11):882-9. doi: 10.7164/antibiotics.54.882. [PubMed:11827029 ]

Showing NP-Card for Chlorogentisylquinone (NP0003990)

MOL for NP0003990 (Chlorogentisylquinone)

3D MOL for NP0003990 (Chlorogentisylquinone)

3D SDF for NP0003990 (Chlorogentisylquinone)

3D-SDF for NP0003990 (Chlorogentisylquinone)

PDB for NP0003990 (Chlorogentisylquinone)

3D PDB for NP0003990 (Chlorogentisylquinone)

SMILES for NP0003990 (Chlorogentisylquinone)

INCHI for NP0003990 (Chlorogentisylquinone)

Structure for NP0003990 (Chlorogentisylquinone)

3D Structure for NP0003990 (Chlorogentisylquinone)