NP-MRD: Showing NP-Card for 2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol (NP0302010)

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Record Information

Version

2.0

Created at

2022-09-10 15:18:08 UTC

Updated at

2022-09-10 15:18:08 UTC

NP-MRD ID

NP0302010

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol

Description

2-(3-Bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3,6-dihydro-2H-pyran-3-ol belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom. 2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol is found in Aplysia dactylomela. 2-(3-Bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3,6-dihydro-2H-pyran-3-ol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -2.4429    2.2766   -0.8998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0973    1.1249    0.0551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1105    1.7634    1.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2206    0.1901    0.0246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0081   -1.1366    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -1.5274    0.2787 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3610   -2.8657    0.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7565   -0.6430   -0.6662 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2073   -0.8144   -2.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6697   -1.1227   -0.5337 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6430   -0.3410   -1.3662 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2235    0.7682   -0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815    0.0935    0.3777 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8631    1.0791    1.3371 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212   -0.5344   -0.7609 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.6322   -1.0884    1.0208 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0731   -1.0430    2.9129 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.1362   -1.0878    0.9096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8836    0.6522   -0.2842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8706    2.1807   -1.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2387    3.2580   -0.4450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5146    2.2531   -1.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1544    1.7616    1.8481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8081    2.8233    1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4899    1.1571    2.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2464    0.5219   -0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8126   -1.8479    0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2439   -1.2905    1.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -3.3645    0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7596   -1.7244   -2.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3060   -0.9355   -2.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9512    0.1072   -2.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7607   -2.1828   -0.8593 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2374    0.0354   -2.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5087   -1.0021   -1.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7247    1.4936   -1.1939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4647    1.2826    0.0976 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3494    0.5548    2.1726 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0400    1.7485    1.6735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5692    1.7337    0.7743 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197   -2.0611    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7693   -2.0084    1.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6988   -0.2379    1.4683 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2 19  1  0
 19  8  1  0
  8  9  1  6
  8  6  1  0
  6  7  1  0
  6  5  1  0
  5  4  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  6
 13 16  1  0
 16 17  1  0
 16 18  1  0
  4  2  1  0
 18 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
  6 28  1  1
  7 29  1  0
  5 27  1  0
  4 26  1  0
 10 33  1  6
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 16 41  1  6
 18 42  1  0
 18 43  1  0
M  END


  Mrv1533004241502542D          

 19 20  0  0  0  0            999 V2000
    1.7751   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -1.4570    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7717   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -2.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -3.5195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5303   -1.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2414   -3.0572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0539   -3.2005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3360   -3.9757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8057   -4.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5202   -5.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236   -5.3830    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.9933   -4.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630   -5.0965    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7111   -3.6892    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  2 10  1  0  0  0  0
  5 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
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0302010

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)OC(C)(C(O)C=C1)C1CCC(C)(Cl)C(Br)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24BrClO2/c1-13(2)7-6-12(18)15(4,19-13)10-5-8-14(3,17)11(16)9-10/h6-7,10-12,18H,5,8-9H2,1-4H3

> <INCHI_KEY>
SMPLCEQWPNQHKL-UHFFFAOYSA-N

> <FORMULA>
C15H24BrClO2

> <MOLECULAR_WEIGHT>
351.71

> <EXACT_MASS>
350.064821

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.63869416191058

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3,6-dihydro-2H-pyran-3-ol

> <ALOGPS_LOGP>
4.61

> <JCHEM_LOGP>
3.7153174316666666

> <ALOGPS_LOGS>
-5.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.606823030728311

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4081756063594364

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
83.18969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3H-pyran-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

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       3.313  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.324  -1.950   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.657  -2.720   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.174  -3.992   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.324  -5.030   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.324  -6.570   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.990  -4.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.990  -2.720   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.184  -5.707   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.701  -5.974   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.227  -7.421   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.237  -8.601   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.571  -9.371   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       4.711 -10.048   0.000  0.00  0.00          Cl+0
HETATM   17  C   UNK     0       3.721  -8.334   0.000  0.00  0.00           C+0
HETATM   18 Br   UNK     0       2.731  -9.513   0.000  0.00  0.00          Br+0
HETATM   19  C   UNK     0       3.194  -6.887   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    2                                                       
CONECT   11    5   12   19                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   11                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄BrClO₂

Average Mass

351.7100 Da

Monoisotopic Mass

350.06482 Da

IUPAC Name

2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3,6-dihydro-2H-pyran-3-ol

Traditional Name

2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3H-pyran-3-ol

CAS Registry Number

Not Available

SMILES

CC1(C)OC(C)(C(O)C=C1)C1CCC(C)(Cl)C(Br)C1

InChI Identifier

InChI=1S/C15H24BrClO2/c1-13(2)7-6-12(18)15(4,19-13)10-5-8-14(3,17)11(16)9-10/h6-7,10-12,18H,5,8-9H2,1-4H3

InChI Key

SMPLCEQWPNQHKL-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
Aplysia dactylomela	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexyl halides. These are organohalogen compounds containing a monocyclic cyclohexane moiety that is substituted at one or more positions by an halogen atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Alkyl halides

Sub Class

Cyclohexyl halides

Direct Parent

Cyclohexyl halides

Alternative Parents

Substituents

Cyclohexyl halide
Pyran
Secondary alcohol
Dialkyl ether
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organochloride
Organobromide
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Alkyl bromide
Alkyl chloride
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	4.61	ALOGPS
logP	3.72	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	83.19 m³·mol⁻¹	ChemAxon
Polarizability	33.64 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

14314420

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol (NP0302010)

MOL for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

3D MOL for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

3D SDF for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

3D-SDF for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

PDB for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

3D PDB for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

SMILES for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

INCHI for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

Structure for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)

3D Structure for NP0302010 (2-(3-bromo-4-chloro-4-methylcyclohexyl)-2,6,6-trimethyl-3h-pyran-3-ol)