NP-MRD: Showing NP-Card for Thiophanic acid (NP0074301)

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Record Information

Version

2.0

Created at

2022-04-28 19:27:31 UTC

Updated at

2022-04-28 19:27:31 UTC

NP-MRD ID

NP0074301

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Thiophanic acid

Description

2,4,5,7-Tetrachloro-1,3,6-trihydroxy-8-methyl-9H-xanthen-9-one belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Thiophanic acid is found in Lecanora iseana. 2,4,5,7-Tetrachloro-1,3,6-trihydroxy-8-methyl-9H-xanthen-9-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.2189   -2.4909   -0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2312   -1.0111   -0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.3209   -0.2300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9339   -1.1907   -0.4351 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.4237    1.0446   -0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6491    1.7279   -0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2235    1.6661    0.1186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1932    3.3960    0.3679 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0061    1.0102    0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    1.6465    0.2412 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3148    1.0741    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4332    1.8603    0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3595    3.5923    0.6389 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.6680    1.2579    0.3743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8263    2.0534    0.5500 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7608   -0.0899    0.1863 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3278   -0.8740    0.1575 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6086   -0.8831    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7448   -2.2257   -0.1738 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.2999    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1862   -1.0124   -0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2005   -2.2482   -0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0231   -0.3529   -0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8525   -3.0431    0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605   -2.7924   -1.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926   -2.8405   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6058    2.7352    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7311    1.6020    0.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935   -2.9908   -0.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  7  9  1  0
  9 23  2  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 18  2  0
 18 19  1  0
 18 16  1  0
 16 17  1  0
 16 14  2  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11 10  1  0
 23  2  1  0
 11 20  1  0
 10  9  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  6 27  1  0
 19 29  1  0
 15 28  1  0
M  END


  Mrv1533004171519442D          

 23 25  0  0  0  0            999 V2000
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 Cl  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
    0.7145   -1.2375    0.0000 O   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
    2.1434   -0.4125    0.0000 Cl  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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   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
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 11 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
  2 23  1  0  0  0  0
  9 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0074301

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(Cl)C(O)=C(Cl)C2=C1C(=O)C1=C(O)C(Cl)=C(O)C(Cl)=C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H6Cl4O5/c1-2-3-9(19)4-10(20)6(16)12(22)8(18)14(4)23-13(3)7(17)11(21)5(2)15/h20-22H,1H3

> <INCHI_KEY>
MYBIAUJNAXMGTF-UHFFFAOYSA-N

> <FORMULA>
C14H6Cl4O5

> <MOLECULAR_WEIGHT>
396.0

> <EXACT_MASS>
393.8969341

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
34.161549572773154

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,4,5,7-tetrachloro-1,3,6-trihydroxy-8-methyl-9H-xanthen-9-one

> <ALOGPS_LOGP>
5.11

> <JCHEM_LOGP>
5.62854435

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.104245244918987

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.485109798743317

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8384130026814876

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
87.01939999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,5,7-tetrachloro-1,3,6-trihydroxy-8-methylxanthen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       1.334  -5.390   0.000  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       4.001  -0.770   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13 Cl   UNK     0       9.336  -0.770   0.000  0.00  0.00          Cl+0
HETATM   14  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   17 Cl   UNK     0      12.003  -5.390   0.000  0.00  0.00          Cl+0
HETATM   18  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       9.336  -6.930   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   23                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   20                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   11   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21    2    9                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

View in JSmol

Synonyms

Value	Source
THIOPHANate	Generator

Chemical Formula

C₁₄H₆Cl₄O₅

Average Mass

396.0000 Da

Monoisotopic Mass

393.89693 Da

IUPAC Name

2,4,5,7-tetrachloro-1,3,6-trihydroxy-8-methyl-9H-xanthen-9-one

Traditional Name

2,4,5,7-tetrachloro-1,3,6-trihydroxy-8-methylxanthen-9-one

CAS Registry Number

Not Available

SMILES

CC1=C(Cl)C(O)=C(Cl)C2=C1C(=O)C1=C(O)C(Cl)=C(O)C(Cl)=C1O2

InChI Identifier

InChI=1S/C14H6Cl4O5/c1-2-3-9(19)4-10(20)6(16)12(22)8(18)14(4)23-13(3)7(17)11(21)5(2)15/h20-22H,1H3

InChI Key

MYBIAUJNAXMGTF-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
Lecanora iseana	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Xanthone
Chromone
4-halophenol
2-halophenol
Phenol
Pyranone
Aryl chloride
Aryl halide
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Polyol
Organooxygen compound
Organochloride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	5.11	ALOGPS
logP	5.63	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	87.02 m³·mol⁻¹	ChemAxon
Polarizability	34.16 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

325789

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Thiophanic acid (NP0074301)

MOL for NP0074301 (Thiophanic acid)

3D MOL for NP0074301 (Thiophanic acid)

3D SDF for NP0074301 (Thiophanic acid)

3D-SDF for NP0074301 (Thiophanic acid)

PDB for NP0074301 (Thiophanic acid)

3D PDB for NP0074301 (Thiophanic acid)

SMILES for NP0074301 (Thiophanic acid)

INCHI for NP0074301 (Thiophanic acid)

Structure for NP0074301 (Thiophanic acid)

3D Structure for NP0074301 (Thiophanic acid)