NP-MRD: Showing NP-Card for (3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane (NP0263095)

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Record Information

Version

2.0

Created at

2022-09-08 06:09:54 UTC

Updated at

2022-09-08 06:09:54 UTC

NP-MRD ID

NP0263095

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane

Description

Apakaochtodene B belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom. (3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane is found in Ochtodes secundiramea. (3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane was first documented in 2003 (PMID: 12919799). Based on a literature review a small amount of articles have been published on Apakaochtodene B (PMID: 12828455) (PMID: 26519589).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
    2.4838    0.9128   -0.8899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3811    0.2835   -0.0270 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7946    0.5630    1.4184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3125   -1.1707   -0.3139 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2470   -2.2384    1.3166 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.1421   -1.5937   -1.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1771   -1.1045   -0.6079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3279   -1.1396   -1.9908 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.1114    0.2737   -0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1460    0.7907    0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4289    0.0708    0.7572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7708   -0.0529    2.4987 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.1289    1.0463   -0.2942 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0256    2.5495    0.6421 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.4201    0.3448   -0.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6571    1.9364   -0.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1763    0.9507   -1.9469 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3146   -0.2881    1.8676 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9335    0.8311    2.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4970    1.4342    1.4731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2320   -1.4934   -0.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046   -2.7029   -1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3035   -1.2959   -2.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852   -1.8008    0.1436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0402    1.8247    0.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2884    0.6247    0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4142   -0.9186    0.3038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1355    1.3626   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
  9 13  1  0
 13 14  1  0
 13  2  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  6
  6 22  1  0
  6 23  1  0
  7 24  1  1
 10 25  1  0
 11 26  1  0
 11 27  1  0
 13 28  1  6
M  END


  Mrv1652309082208092D          

 14 14  0  0  0  0            999 V2000
    1.2448    1.8695    0.0000 C   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    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    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
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 Cl  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
  4  6  1  0  0  0  0
  6  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 13  1  0  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0263095

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(Br)CC(Cl)\C(=C/CCl)C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C10H14BrCl3/c1-10(2)8(11)5-7(13)6(3-4-12)9(10)14/h3,7-9H,4-5H2,1-2H3/b6-3+

> <INCHI_KEY>
WMQLQCCLGFMTKH-ZZXKWVIFSA-N

> <FORMULA>
C10H14BrCl3

> <MOLECULAR_WEIGHT>
320.48

> <EXACT_MASS>
317.934447

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
27.59694745232531

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane

> <JCHEM_LOGP>
4.2942582693333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.94040000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0       4.001   2.310   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0      -0.000  -3.080   0.000  0.00  0.00          Cl+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -1.334   2.310   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4   13                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13    9    2   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Apakaochtodene a	MeSH

Chemical Formula

C₁₀H₁₄BrCl₃

Average Mass

320.4800 Da

Monoisotopic Mass

317.93445 Da

IUPAC Name

(3E)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane

Traditional Name

(3E)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane

CAS Registry Number

Not Available

SMILES

CC1(C)C(Br)CC(Cl)\C(=C/CCl)C1Cl

InChI Identifier

InChI=1S/C10H14BrCl3/c1-10(2)8(11)5-7(13)6(3-4-12)9(10)14/h3,7-9H,4-5H2,1-2H3/b6-3+

InChI Key

WMQLQCCLGFMTKH-ZZXKWVIFSA-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
Ochtodes secundiramea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as organochlorides. Organochlorides are compounds containing a chemical bond between a carbon atom and a chlorine atom.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Organochlorides

Sub Class

Not Available

Direct Parent

Organochlorides

Alternative Parents

Substituents

Hydrocarbon derivative
Organochloride
Organobromide
Alkyl halide
Alkyl chloride
Alkyl bromide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	4.29	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.94 m³·mol⁻¹	ChemAxon
Polarizability	27.6 Å³	ChemAxon
Number of Rings	1	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

C00049424

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

101253647

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Polzin JJ, Rorrer GL, Cheney DP: Metabolic flux analysis of halogenated monoterpene biosynthesis in microplantlets of the macrophytic red alga Ochtodes secundiramea. Biomol Eng. 2003 Jul;20(4-6):205-15. doi: 10.1016/s1389-0344(03)00054-6. [PubMed:12919799 ]
Barahona LF, Rorrer GL: Isolation of halogenated monoterpenes from bioreactor-cultured microplantlets of the macrophytic red algae Ochtodes secundiramea and Portieria hornemannii. J Nat Prod. 2003 Jun;66(6):743-51. doi: 10.1021/np0206007. [PubMed:12828455 ]
Perez-Lopez P, Jeffryes C, Agathos SN, Feijoo G, Rorrer G, Moreira MT: Environmental life cycle optimization of essential terpene oils produced by the macroalga Ochtodes secundiramea. Sci Total Environ. 2016 Jan 15;542(Pt A):292-305. doi: 10.1016/j.scitotenv.2015.10.045. Epub 2015 Oct 29. [PubMed:26519589 ]
LOTUS database [Link]

Showing NP-Card for (3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane (NP0263095)

MOL for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

3D MOL for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

3D SDF for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

3D-SDF for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

PDB for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

3D PDB for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

SMILES for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

INCHI for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

Structure for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)

3D Structure for NP0263095 ((3e)-6-bromo-2,4-dichloro-3-(2-chloroethylidene)-1,1-dimethylcyclohexane)