NP-MRD: Showing NP-Card for 2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one (NP0215501)

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Record Information

Version

2.0

Created at

2022-09-05 15:08:39 UTC

Updated at

2022-09-05 15:08:39 UTC

NP-MRD ID

NP0215501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one

Description

2-[(2,3,6-Tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one is found in Symphyocladia latiuscula. 2-[(2,3,6-Tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -0.8348    0.0766   -1.8859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4894   -0.3466   -0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9418   -0.0807   -0.9696 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3124    0.6250    0.2996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074   -0.1385    1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0559   -1.3675    1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8993   -1.1161    0.1431 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1143   -0.3608    0.8933 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384    0.0487    0.2950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -0.7710    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1399   -2.5796    0.5737 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.5692   -0.3523   -0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5929   -1.2495   -0.7496 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7047    0.9885   -0.9019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8877    1.4161   -1.4906 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6434    1.8432   -0.6613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8066    3.6871   -1.1568 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4794    1.3812   -0.0726 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0811    2.6525    0.2123 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5394   -1.0064   -1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2401    0.5963   -1.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8433    1.6382    0.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4112    0.8141    0.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2380    0.4791    2.1988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7146   -0.4871    2.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7017   -2.1830    0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5646   -1.7651    2.0488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6130   -2.1487   -0.1445 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3759   -0.9924    1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3931    0.5186    1.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4979   -2.2154   -0.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9579    2.3955   -1.7477 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 10  1  0
 10 11  1  0
 10  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  9 18  1  0
 18 19  1  0
 18 16  2  0
 16 17  1  0
 16 14  1  0
  2  7  1  0
 15 32  1  0
 13 31  1  0
  8 29  1  0
  8 30  1  0
  7 28  1  6
  6 26  1  0
  6 27  1  0
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 20  1  0
  3 21  1  0
M  END


  Mrv1533004161501512D          

 19 20  0  0  0  0            999 V2000
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -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
   -2.1434   -1.2375    0.0000 O   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
   -2.1434   -2.8875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   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
    0.0000   -4.1250    0.0000 C   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
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Br  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
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(O)C(Br)=C(CC2CCCCC2=O)C(Br)=C1Br

> <INCHI_IDENTIFIER>
InChI=1S/C13H13Br3O3/c14-9-7(5-6-3-1-2-4-8(6)17)10(15)12(18)13(19)11(9)16/h6,18-19H,1-5H2

> <INCHI_KEY>
LLMBLIAKCCQZSI-UHFFFAOYSA-N

> <FORMULA>
C13H13Br3O3

> <MOLECULAR_WEIGHT>
456.956

> <EXACT_MASS>
453.841483

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
33.3251180741305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one

> <ALOGPS_LOGP>
4.78

> <JCHEM_LOGP>
5.308680413333333

> <ALOGPS_LOGS>
-4.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.16695252063169

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.769499810698889

> <JCHEM_PKA_STRONGEST_BASIC>
-7.417219429725636

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
84.3481

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6 Br   UNK     0      -4.001  -5.390   0.000  0.00  0.00          Br+0
HETATM    7  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       1.334  -5.390   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   19 Br   UNK     0       1.334  -2.310   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16    7   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    2   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₃Br₃O₃

Average Mass

456.9560 Da

Monoisotopic Mass

453.84148 Da

IUPAC Name

2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one

Traditional Name

2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one

CAS Registry Number

Not Available

SMILES

OC1=C(O)C(Br)=C(CC2CCCCC2=O)C(Br)=C1Br

InChI Identifier

InChI=1S/C13H13Br3O3/c14-9-7(5-6-3-1-2-4-8(6)17)10(15)12(18)13(19)11(9)16/h6,18-19H,1-5H2

InChI Key

LLMBLIAKCCQZSI-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
Symphyocladia latiuscula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

4-bromophenol
Catechol
2-bromophenol
3-bromophenol
2-halophenol
3-halophenol
4-halophenol
Bromobenzene
Halobenzene
Aryl bromide
Aryl halide
Monocyclic benzene moiety
Cyclic ketone
Ketone
Organic oxygen compound
Organohalogen compound
Organobromide
Carbonyl group
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	4.78	ALOGPS
logP	5.31	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	6.77	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	84.35 m³·mol⁻¹	ChemAxon
Polarizability	33.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

85122855

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one (NP0215501)

MOL for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

3D MOL for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

3D SDF for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

3D-SDF for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

PDB for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

3D PDB for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

SMILES for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

INCHI for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

Structure for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)

3D Structure for NP0215501 (2-[(2,3,6-tribromo-4,5-dihydroxyphenyl)methyl]cyclohexan-1-one)