NP-MRD: Showing NP-Card for 2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one (NP0262933)

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Record Information

Version

2.0

Created at

2022-09-08 05:57:14 UTC

Updated at

2022-09-08 05:57:14 UTC

NP-MRD ID

NP0262933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one

Description

Ditropolonyl sulfide belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups. 2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one is found in Burkholderia cepacia. Ditropolonyl sulfide is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
    1.2632    2.1794   -0.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0101    1.1770   -0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101    1.1573   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4579    2.2281   -1.6947 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2268    0.2162   -0.8179 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1038   -1.0540   -0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0900   -1.6181    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9048   -1.0359    0.9195 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4734    0.2600    0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0825    0.8213    1.7288 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4650    0.5029    0.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884    1.4622    0.0626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0526    1.4813   -0.8073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9949    0.4840   -0.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0701   -0.7466   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2008   -1.2859    0.5879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5387   -2.5725    0.9819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -0.7230    1.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -1.4046    2.0257 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8004    2.9884   -1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1843    0.4773   -1.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9169   -1.7349   -0.5085 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2086   -2.6555    0.7392 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2260   -1.6468    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4459    2.3957    0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2030    2.3563   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7657    0.6836   -1.7120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9340   -1.3549   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9487   -3.0384    1.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
  2  1  2  0
 11 18  1  0
 18 19  2  0
 18 16  1  0
  2  9  1  0
 17 29  1  0
 15 28  1  0
 14 27  1  0
 13 26  1  0
 12 25  1  0
  8 24  1  0
  7 23  1  0
  6 22  1  0
  5 21  1  0
  4 20  1  0
M  END


  Mrv1533004191522062D          

 19 20  0  0  0  0            999 V2000
    1.7631   -0.7508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7631   -1.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0198   -1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8362   -2.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506   -3.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1756   -3.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6900   -2.7380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943   -2.9216    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -3.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5533   -3.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9658   -4.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6644   -5.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8760   -5.5585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1944   -5.0938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4799   -5.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1327   -4.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648   -3.9697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5064   -1.9337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1514   -1.4193    0.0000 O   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  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
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
  7 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0262933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC=C(SC2=CC=CC=C(O)C2=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H10O4S/c15-9-5-1-3-7-11(13(9)17)19-12-8-4-2-6-10(16)14(12)18/h1-8H,(H,15,17)(H,16,18)

> <INCHI_KEY>
GRAKHGFVPASAHI-UHFFFAOYSA-N

> <FORMULA>
C14H10O4S

> <MOLECULAR_WEIGHT>
274.29

> <EXACT_MASS>
274.029979976

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
26.74211437432459

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one

> <ALOGPS_LOGP>
2.21

> <JCHEM_LOGP>
2.2588134036666667

> <ALOGPS_LOGS>
-3.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.896356256276308

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.214970913648115

> <JCHEM_PKA_STRONGEST_BASIC>
-3.12856120226689

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
82.83709999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  O   UNK     0       3.291  -1.401   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.291  -2.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.904  -3.610   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.561  -5.111   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.521  -6.315   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.061  -6.315   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.021  -5.111   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       6.523  -5.454   0.000  0.00  0.00           S+0
HETATM    9  C   UNK     0       6.977  -6.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.499  -7.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.269  -8.488   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.707  -9.922   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.235 -10.376   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.963  -9.508   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.629 -10.278   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.848  -7.973   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.414  -7.410   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.679  -3.610   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.883  -2.649   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9   17                                                  
CONECT   17   16                                                            
CONECT   18    7    2   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
Ditropolonyl sulphide	Generator

Chemical Formula

C₁₄H₁₀O₄S

Average Mass

274.2900 Da

Monoisotopic Mass

274.02998 Da

IUPAC Name

2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one

Traditional Name

2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one

CAS Registry Number

Not Available

SMILES

OC1=CC=CC=C(SC2=CC=CC=C(O)C2=O)C1=O

InChI Identifier

InChI=1S/C14H10O4S/c15-9-5-1-3-7-11(13(9)17)19-12-8-4-2-6-10(16)14(12)18/h1-8H,(H,15,17)(H,16,18)

InChI Key

GRAKHGFVPASAHI-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
Burkholderia cepacia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thioethers

Sub Class

Aryl thioethers

Direct Parent

Diarylthioethers

Alternative Parents

Substituents

Diarylthioether
Tropolone
Tropone
Vinylogous thioester
Cyclic ketone
Sulfenyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.21	ALOGPS
logP	2.26	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	10.21	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.84 m³·mol⁻¹	ChemAxon
Polarizability	26.74 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

3067843

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one (NP0262933)

MOL for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

3D MOL for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

3D SDF for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

3D-SDF for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

PDB for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

3D PDB for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

SMILES for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

INCHI for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

Structure for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)

3D Structure for NP0262933 (2-hydroxy-7-[(6-hydroxy-7-oxocyclohepta-1,3,5-trien-1-yl)sulfanyl]cyclohepta-2,4,6-trien-1-one)