NP-MRD: Showing NP-Card for (3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran (NP0324871)

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Record Information

Version

2.0

Created at

2022-09-12 05:12:16 UTC

Updated at

2022-09-12 05:12:16 UTC

NP-MRD ID

NP0324871

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran

Description

(3S)-3-bromo-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydro-2H-pyran 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. (3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran is found in Aplysia dactylomela. Based on a literature review very few articles have been published on (3S)-3-bromo-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydro-2H-pyran.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -0.3940    1.8156    1.6460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1311    0.7364    0.9992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5204   -0.1390    0.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8737   -0.2161   -0.1400 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7316    0.9857   -0.1181 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8664    0.7355   -1.1528 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6381   -0.4694   -0.7234 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4236   -0.1709    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8306   -0.8167   -2.0124 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.7871   -1.7067   -0.5810 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8815   -3.0549    0.2855 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.5802   -1.4835    0.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880   -1.1779   -0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6269   -0.4398   -1.0434 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9007    0.8905   -2.2330 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.3834    0.2468    0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0189    1.5409   -0.3826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4386   -0.7032    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5135    0.5657    1.1554 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5145    1.5299    2.1872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0570    2.1628    2.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3510    2.7002    1.0146 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8241   -0.4471   -1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2027    1.8497   -0.5162 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3278    1.1594    0.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.5369   -2.1466 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5450    1.5910   -1.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4801   -0.5068    0.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4448    0.9012    0.7880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9414   -0.7505    1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5150   -2.1093   -1.5708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8854   -2.3197    0.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9308   -1.4557    1.3338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9796   -1.7760   -1.1231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8718   -1.8244    0.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2241   -1.1991   -1.5515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4994    1.9740   -1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0689    2.3001    0.4285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0781    1.2879   -0.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7697   -1.4004   -0.1487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0231   -1.2419    1.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2964   -0.1011    0.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  6
  7 10  1  0
 10 11  1  0
 10 12  1  0
 19  2  1  0
 12  4  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  6
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 18 42  1  0
  4 23  1  6
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  6
 12 32  1  0
 12 33  1  0
M  END


  Mrv1652309122207122D          

 19 20  0  0  1  0            999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
    1.2448   -5.9945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -5.9945    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 Br  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
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842   -0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448   -0.6055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  7 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
  4 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324871

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C[C@H](Br)C(C)(C)O1)[C@H]1CC[C@](C)(Cl)[C@@H](Br)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H23Br2ClO/c1-9-11(8-12(16)14(2,3)19-9)10-5-6-15(4,18)13(17)7-10/h10,12-13H,5-8H2,1-4H3/t10-,12-,13-,15-/m0/s1

> <INCHI_KEY>
CGXATWIPOMXJIC-NHULGOKLSA-N

> <FORMULA>
C15H23Br2ClO

> <MOLECULAR_WEIGHT>
414.61

> <EXACT_MASS>
411.980419

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
36.172962854032065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S)-3-bromo-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydro-2H-pyran

> <JCHEM_LOGP>
4.780131827333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.796250708076932

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
89.70680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-bromo-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.324 -11.190   0.000  0.00  0.00           C+0
HETATM    9 Cl   UNK     0       0.344 -11.190   0.000  0.00  0.00          Cl+0
HETATM   10  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   11 Br   UNK     0      -1.334 -10.010   0.000  0.00  0.00          Br+0
HETATM   12  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0      -1.334  -2.310   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.344  -1.130   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.324  -1.130   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    4                                                       
CONECT   13    3   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₃Br₂ClO

Average Mass

414.6100 Da

Monoisotopic Mass

411.98042 Da

IUPAC Name

(3S)-3-bromo-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydro-2H-pyran

Traditional Name

(3S)-3-bromo-5-[(1S,3S,4S)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran

CAS Registry Number

Not Available

SMILES

CC1=C(C[C@H](Br)C(C)(C)O1)[C@H]1CC[C@](C)(Cl)[C@@H](Br)C1

InChI Identifier

InChI=1S/C15H23Br2ClO/c1-9-11(8-12(16)14(2,3)19-9)10-5-6-15(4,18)13(17)7-10/h10,12-13H,5-8H2,1-4H3/t10-,12-,13-,15-/m0/s1

InChI Key

CGXATWIPOMXJIC-NHULGOKLSA-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
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organobromide
Alkyl chloride
Alkyl bromide
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	4.78	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.71 m³·mol⁻¹	ChemAxon
Polarizability	36.17 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

163009326

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran (NP0324871)

MOL for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

3D MOL for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

3D SDF for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

3D-SDF for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

PDB for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

3D PDB for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

SMILES for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

INCHI for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

Structure for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)

3D Structure for NP0324871 ((3s)-3-bromo-5-[(1s,3s,4s)-3-bromo-4-chloro-4-methylcyclohexyl]-2,2,6-trimethyl-3,4-dihydropyran)