NP-MRD: Showing NP-Card for 3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene (NP0286800)

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Record Information

Version

2.0

Created at

2022-09-09 15:33:13 UTC

Updated at

2022-09-09 15:33:13 UTC

NP-MRD ID

NP0286800

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene

Description

3,8-Dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]Dodec-9-ene belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae. 3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene is found in Laurencia pacifica. 3,8-Dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]Dodec-9-ene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
    0.0163    2.6312   -0.0433 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7474    1.5760   -0.1596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1023    1.7883   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069    0.7670   -1.1540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806   -0.5502   -1.0522 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1529   -2.0354   -1.5307 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9376   -0.3855   -1.8463 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1397   -0.5597   -1.0521 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4460   -0.0118   -1.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4082   -0.5797   -0.3871 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8261   -0.1306   -0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3346   -2.3616   -0.6283 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.0495   -0.2846    1.0166 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3244    1.0285    1.7262 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6497    0.1125    1.3149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3036    0.1977    0.2092 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6003   -0.5959    0.4073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5480    0.0822    1.3329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3355   -2.0313    0.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0141    2.5281    0.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3390    3.5996   -0.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5687    2.7634   -0.6934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7947    0.8594   -1.5707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2464   -1.6345   -0.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5107    1.0855   -1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8149   -0.4219   -2.4052 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4913   -0.7640   -0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0587   -0.3418   -1.7058 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9762    0.9062   -0.3410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3010   -1.2177    1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6996    1.1436    1.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2752   -0.5081    2.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6737   -0.5807    2.2375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5357    0.1810    0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414    1.0297    1.7096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3086   -2.2423    1.0529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201   -2.3122    1.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5857   -2.7304   -0.1047 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  1  0
 17  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  1
 10 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16  2  1  6
  2  1  2  3
  2  3  1  0
  3  4  2  0
 16 17  1  0
  4  5  1  0
 16  8  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 19 36  1  0
 19 37  1  0
 19 38  1  0
  8 24  1  1
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 13 30  1  1
 15 31  1  0
 15 32  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
M  END


  Mrv1533004241517142D          

 19 21  0  0  0  0            999 V2000
    0.4893    0.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126   -0.1555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2915   -0.5564    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.5475    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3606    0.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9613    0.9477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7470    0.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2089    1.2515    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.3956   -0.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2480   -0.8694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -1.0739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2114   -1.8756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240   -0.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1062   -1.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2802   -0.9422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7413   -1.5669    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.2855    0.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6157   -0.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0503   -0.3091    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
  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  2  0  0  0  0
 11 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 13 17  1  0  0  0  0
  7 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0286800

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2(Br)OC3CC(C)(Cl)C(Br)CC13C(=C)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H19Br2ClO/c1-9-5-6-15(17)12(2,3)14(9)7-10(16)13(4,18)8-11(14)19-15/h5-6,10-11H,1,7-8H2,2-4H3

> <INCHI_KEY>
SCVKJKKRVLDQHS-UHFFFAOYSA-N

> <FORMULA>
C15H19Br2ClO

> <MOLECULAR_WEIGHT>
410.57

> <EXACT_MASS>
407.949119

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
34.35360964195336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
4.736254917

> <ALOGPS_LOGS>
-6.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.299935305670168

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
86.9964

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.52e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene

> <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       0.913   0.900   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.890  -0.290   0.000  0.00  0.00           C+0
HETATM    3 Cl   UNK     0       0.544  -1.039   0.000  0.00  0.00          Cl+0
HETATM    4  C   UNK     0       2.889   0.885   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.406   0.596   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.528   1.769   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.994   1.060   0.000  0.00  0.00           C+0
HETATM    8 Br   UNK     0       7.857   2.336   0.000  0.00  0.00          Br+0
HETATM    9  C   UNK     0       8.205  -0.041   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.930  -1.623   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.358  -2.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.995  -3.501   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.085  -0.900   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.932  -2.040   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.390  -1.759   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       1.384  -2.925   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       6.133   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.749  -1.411   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.561  -0.577   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   15                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   17                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14   17                                             
CONECT   14   13   15                                                       
CONECT   15   14    2   16                                                  
CONECT   16   15                                                            
CONECT   17   13    7   18   19                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉Br₂ClO

Average Mass

410.5700 Da

Monoisotopic Mass

407.94912 Da

IUPAC Name

3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene

Traditional Name

3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene

CAS Registry Number

Not Available

SMILES

CC1(C)C2(Br)OC3CC(C)(Cl)C(Br)CC13C(=C)C=C2

InChI Identifier

InChI=1S/C15H19Br2ClO/c1-9-5-6-15(17)12(2,3)14(9)7-10(16)13(4,18)8-11(14)19-15/h5-6,10-11H,1,7-8H2,2-4H3

InChI Key

SCVKJKKRVLDQHS-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
Laurencia pacifica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Chamigranes

Alternative Parents

Substituents

Chamigrane sesquiterpenoid
Tetrahydrofuran
Dialkyl ether
Ether
Organoheterocyclic compound
Oxacycle
Organochloride
Organobromide
Organohalogen compound
Alkyl bromide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Alkyl chloride
Alkyl halide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.53	ALOGPS
logP	4.74	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-4.3	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	0	ChemAxon
Refractivity	87 m³·mol⁻¹	ChemAxon
Polarizability	34.35 Å³	ChemAxon
Number of Rings	3	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

182147

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene (NP0286800)

MOL for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

3D MOL for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

3D SDF for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

3D-SDF for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

PDB for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

3D PDB for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

SMILES for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

INCHI for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

Structure for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)

3D Structure for NP0286800 (3,8-dibromo-4-chloro-4,12,12-trimethyl-11-methylidene-7-oxatricyclo[6.3.1.0¹,⁶]dodec-9-ene)