NP-MRD: Showing NP-Card for 3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol (NP0196504)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 14:36:33 UTC

Updated at

2022-09-04 14:36:33 UTC

NP-MRD ID

NP0196504

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol

Description

3-Bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]Dodecane-4,6-diol 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-Bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]Dodecane-4,6-diol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.2327   -0.3517    1.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7045   -0.4427    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1370   -1.8552   -0.2691 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4838    0.5110   -0.6529 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2163   -0.3487   -2.2598 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8125    1.7370   -1.1220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5932    2.9042   -0.9425 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4940    2.0191   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3191    0.7731   -0.6829 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1051    0.4445   -2.0450 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7806    0.9601   -0.5098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3320   -0.2569    0.2010 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8114   -0.1523    0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8719   -1.5505   -0.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3828   -1.6046   -0.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349   -0.3880    0.1088 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3084   -0.4350    1.5242 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7812   -0.2133    1.6097 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2130    1.2995    2.4275 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8305   -1.1257    2.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381   -0.5713    1.5016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1798    0.6755    1.9933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2650   -1.7924   -0.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7713   -2.1082   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9223   -2.5986    0.5160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4235    0.8519   -0.1182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5884    1.7205   -2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4300    3.2726   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5895    2.2942    0.6094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0095    2.8403   -1.0209 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3980    1.2711   -2.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    1.8414    0.1160 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    1.0645   -1.4674 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2841   -0.8659    0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2652   -0.2745   -0.7568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0891    0.8617    0.5983 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4133   -1.7824   -1.3632 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435   -2.3601    0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1246   -1.4823   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0324   -2.5429   -0.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869    0.2919    2.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1378   -1.4992    1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3211   -1.0321    2.1684 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
  6  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 16  2  1  1
 16  9  1  0
 18 12  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
  4 26  1  1
  6 27  1  6
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  1
M  END


  Mrv1533004231519212D          

 19 21  0  0  0  0            999 V2000
    0.1245   -0.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6234    0.0477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1325   -0.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1426    0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -0.1207    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2121    1.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9442    1.5914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5213    1.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3075    1.3101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0827    1.0278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9802    1.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8857    1.6950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5209    2.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2582    1.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1269    0.6501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4144    0.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3251    0.0999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9624    0.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7402    0.4924    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
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196504

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C(Br)C(O)CC2(O)CC3(C)CCC12CC3Cl

> <INCHI_IDENTIFIER>
InChI=1S/C15H24BrClO2/c1-12(2)11(16)9(18)6-15(19)8-13(3)4-5-14(12,15)7-10(13)17/h9-11,18-19H,4-8H2,1-3H3

> <INCHI_KEY>
ZMHIWDPAJYFEAG-UHFFFAOYSA-N

> <FORMULA>
C15H24BrClO2

> <MOLECULAR_WEIGHT>
351.71

> <EXACT_MASS>
350.064821

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
33.19984044566414

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol

> <ALOGPS_LOGP>
3.46

> <JCHEM_LOGP>
2.803374722666666

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.552143645724591

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.828611296135378

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1334624920693885

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
79.7858

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       0.232  -1.138   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.164   0.089   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.114  -1.123   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.266   0.682   0.000  0.00  0.00           C+0
HETATM    5 Br   UNK     0      -1.511  -0.225   0.000  0.00  0.00          Br+0
HETATM    6  C   UNK     0      -0.396   2.260   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.762   2.971   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.973   3.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.441   2.446   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       3.888   1.918   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.696   3.631   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.387   3.164   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.572   4.147   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.215   2.543   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.970   1.214   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.640   0.728   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.340   0.186   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.530   1.433   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       6.982   0.919   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4   16                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   16                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   18                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2    9   17                                             
CONECT   17   16   18                                                       
CONECT   18   17   12   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄BrClO₂

Average Mass

351.7100 Da

Monoisotopic Mass

350.06482 Da

IUPAC Name

3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol

Traditional Name

3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol

CAS Registry Number

Not Available

SMILES

CC1(C)C(Br)C(O)CC2(O)CC3(C)CCC12CC3Cl

InChI Identifier

InChI=1S/C15H24BrClO2/c1-12(2)11(16)9(18)6-15(19)8-13(3)4-5-14(12,15)7-10(13)17/h9-11,18-19H,4-8H2,1-3H3

InChI Key

ZMHIWDPAJYFEAG-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

Not Available

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
Tertiary alcohol
Cyclic alcohol
Bromohydrin
Secondary alcohol
Halohydrin
Alcohol
Organobromide
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alkyl halide
Alkyl chloride
Alkyl bromide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.46	ALOGPS
logP	2.8	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	13.83	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	79.79 m³·mol⁻¹	ChemAxon
Polarizability	33.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

74052047

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol (NP0196504)

MOL for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

3D MOL for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

3D SDF for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

3D-SDF for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

PDB for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

3D PDB for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

SMILES for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

INCHI for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

Structure for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)

3D Structure for NP0196504 (3-bromo-9-chloro-2,2,8-trimethyltricyclo[6.2.2.0¹,⁶]dodecane-4,6-diol)