NP-MRD: Showing NP-Card for isosulochrin (NP0199690)

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Record Information

Version

2.0

Created at

2022-09-04 18:22:38 UTC

Updated at

2022-09-04 18:22:38 UTC

NP-MRD ID

NP0199690

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isosulochrin

Description

Methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoate belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups. isosulochrin is found in Pestalotiopsis fici, Pestalotiopsis guepinii, Pseudopestalotiopsis theae and Rhizophora apiculata. Methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.1418    1.7463   -2.9076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2898    1.1820   -1.7094 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1233    0.1229   -1.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5404   -0.3904   -2.6638 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059   -0.4908   -0.3289 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7345   -1.3489   -0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3705   -1.7901    0.6832 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4786   -2.6316    0.5993 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1289   -3.0818    1.7737 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9171   -1.4030    1.9246 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8300   -0.5810    2.0426 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3317   -0.1614    3.2518 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1414   -0.1061    0.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0191    0.7828    1.1005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1106    1.6911    2.0297 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2523    0.8046    0.4088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    1.9640    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    3.1100    0.9699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2896    1.9811   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8631    0.8707   -0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2219    0.9650   -1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1126   -0.2776   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -0.3157   -0.1761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0983   -1.4872   -0.1671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3453    2.8327   -2.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6625    1.7126   -3.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0809    1.2671   -3.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0697   -1.6382   -1.4334 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4955   -3.7329    2.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3323   -2.1495    2.3762 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0594   -3.6023    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923   -1.7262    2.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6894   -0.3971    4.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9969    3.9748    0.9810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8685    2.9027   -0.1723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4432    1.9877   -1.7094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3725    0.2096   -2.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9742    0.7416   -0.5415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5279   -1.1782   -1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3827   -2.3591   -0.5430 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 13  5  1  0
 23 16  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 18 34  1  0
 19 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
 22 39  1  0
 24 40  1  0
M  END


  Mrv1533004241507432D          

 24 25  0  0  0  0            999 V2000
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    1.4289    0.0000    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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 O   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
    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 C   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
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513   -3.2287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199690

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(OC)=CC(O)=C1C(=O)C1=C(O)C=C(C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O7/c1-8-4-11(18)15(12(19)5-8)16(21)14-10(17(22)24-3)6-9(23-2)7-13(14)20/h4-7,18-20H,1-3H3

> <INCHI_KEY>
XKIBNYJGNBTYMP-UHFFFAOYSA-N

> <FORMULA>
C17H16O7

> <MOLECULAR_WEIGHT>
332.308

> <EXACT_MASS>
332.089602855

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.958421619935606

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoate

> <ALOGPS_LOGP>
2.49

> <JCHEM_LOGP>
4.831129976

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.27775020669372

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.610284308988489

> <JCHEM_PKA_STRONGEST_BASIC>
-4.855325194982176

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
86.1059

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.003  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.376  -6.027   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   23                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoic acid	Generator

Chemical Formula

C₁₇H₁₆O₇

Average Mass

332.3080 Da

Monoisotopic Mass

332.08960 Da

IUPAC Name

methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoate

Traditional Name

methyl 2-(2,6-dihydroxy-4-methylbenzoyl)-3-hydroxy-5-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(OC)=CC(O)=C1C(=O)C1=C(O)C=C(C)C=C1O

InChI Identifier

InChI=1S/C17H16O7/c1-8-4-11(18)15(12(19)5-8)16(21)14-10(17(22)24-3)6-9(23-2)7-13(14)20/h4-7,18-20H,1-3H3

InChI Key

XKIBNYJGNBTYMP-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
Pestalotiopsis fici	LOTUS Database	35616633
Pestalotiopsis guepinii	LOTUS Database	35616633
Pseudopestalotiopsis theae	LOTUS Database	35616633
Rhizophora apiculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzophenones

Direct Parent

Benzophenones

Alternative Parents

Substituents

Benzophenone
Diphenylmethane
Aryl-phenylketone
M-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoate ester
Benzoic acid or derivatives
M-cresol
Anisole
Phenoxy compound
Benzoyl
Phenol ether
Resorcinol
Aryl ketone
Methoxybenzene
Phenol
Alkyl aryl ether
Toluene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Methyl ester
Vinylogous acid
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	2.49	ALOGPS
logP	4.83	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	86.11 m³·mol⁻¹	ChemAxon
Polarizability	32.96 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

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

16681742

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for isosulochrin (NP0199690)

MOL for NP0199690 (isosulochrin)

3D MOL for NP0199690 (isosulochrin)

3D SDF for NP0199690 (isosulochrin)

3D-SDF for NP0199690 (isosulochrin)

PDB for NP0199690 (isosulochrin)

3D PDB for NP0199690 (isosulochrin)

SMILES for NP0199690 (isosulochrin)

INCHI for NP0199690 (isosulochrin)

Structure for NP0199690 (isosulochrin)

3D Structure for NP0199690 (isosulochrin)