NP-MRD: Showing NP-Card for 5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol (NP0205295)

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Record Information

Version

2.0

Created at

2022-09-05 01:10:07 UTC

Updated at

2022-09-05 01:10:07 UTC

NP-MRD ID

NP0205295

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol

Description

5,5'-Dibromo-3-[(1S,2R,5R)-1,2-dimethylbicyclo[3.1.0]Hexan-2-yl]-3'-[(1S,2S,5R)-1,2-dimethylbicyclo[3.1.0]Hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol is found in Laurencia dendroidea. Based on a literature review very few articles have been published on 5,5'-dibromo-3-[(1S,2R,5R)-1,2-dimethylbicyclo[3.1.0]Hexan-2-yl]-3'-[(1S,2S,5R)-1,2-dimethylbicyclo[3.1.0]Hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203102D          

 34 39  0  0  1  0            999 V2000
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M  END

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M  END


  Mrv1652309052203102D          

 34 39  0  0  1  0            999 V2000
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 21 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 29 31  1  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  1  0  0  0
 24 33  2  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0205295

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(O)=C(C=C1Br)[C@]1(C)CC[C@@H]2C[C@]12C)C1=C(O)C(=CC(Br)=C1C)[C@@]1(C)CC[C@@H]2C[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H36Br2O2/c1-15-21(31)11-19(27(3)9-7-17-13-29(17,27)5)25(33)23(15)24-16(2)22(32)12-20(26(24)34)28(4)10-8-18-14-30(18,28)6/h11-12,17-18,33-34H,7-10,13-14H2,1-6H3/t17-,18-,27-,28+,29+,30+/m1/s1

> <INCHI_KEY>
WNXJPDLXUDICTR-NATJNTQESA-N

> <FORMULA>
C30H36Br2O2

> <MOLECULAR_WEIGHT>
588.424

> <EXACT_MASS>
586.108206

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
58.00811339057541

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,5'-dibromo-3-[(1S,2R,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1S,2S,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol

> <JCHEM_LOGP>
9.450205449999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.83045424483287

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.982135199728758

> <JCHEM_PKA_STRONGEST_BASIC>
-5.956971542680994

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
146.95359999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5,5'-dibromo-3-[(1S,2R,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1S,2S,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.186   7.520   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.520   8.290   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.520   9.830   0.000  0.00  0.00           C+0
HETATM    4 Br   UNK     0       4.186  10.600   0.000  0.00  0.00          Br+0
HETATM    5  C   UNK     0       6.853  10.600   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.187   9.830   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.521  10.600   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.147   9.193   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.616  11.846   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.521  13.092   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.985  12.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.319  11.846   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.985  11.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.612   9.669   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.187   8.290   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.521   7.520   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.853   7.520   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.853   5.980   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.187   5.210   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.521   5.980   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.187   3.670   0.000  0.00  0.00           C+0
HETATM   22 Br   UNK     0       9.521   2.900   0.000  0.00  0.00          Br+0
HETATM   23  C   UNK     0       6.853   2.900   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.520   3.670   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.186   2.900   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.560   4.307   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.091   1.654   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.186   0.408   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.721   0.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.388   1.654   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.721   2.424   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.095   3.831   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.520   5.210   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.186   5.980   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   13                                                       
CONECT   13   12   11    7   14                                             
CONECT   14   13                                                            
CONECT   15    6   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15    2   18                                                  
CONECT   18   17   19   33                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   33                                                  
CONECT   25   24   26   27   31                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29   31                                                       
CONECT   31   30   29   25   32                                             
CONECT   32   31                                                            
CONECT   33   24   18   34                                                  
CONECT   34   33                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆Br₂O₂

Average Mass

588.4240 Da

Monoisotopic Mass

586.10821 Da

IUPAC Name

5,5'-dibromo-3-[(1S,2R,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1S,2S,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol

Traditional Name

5,5'-dibromo-3-[(1S,2R,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1S,2S,5R)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol

CAS Registry Number

Not Available

SMILES

CC1=C(C(O)=C(C=C1Br)[C@]1(C)CC[C@@H]2C[C@]12C)C1=C(O)C(=CC(Br)=C1C)[C@@]1(C)CC[C@@H]2C[C@]12C

InChI Identifier

InChI=1S/C30H36Br2O2/c1-15-21(31)11-19(27(3)9-7-17-13-29(17,27)5)25(33)23(15)24-16(2)22(32)12-20(26(24)34)28(4)10-8-18-14-30(18,28)6/h11-12,17-18,33-34H,7-10,13-14H2,1-6H3/t17-,18-,27-,28+,29+,30+/m1/s1

InChI Key

WNXJPDLXUDICTR-NATJNTQESA-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 dendroidea	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Cyclolaurane sesquiterpenoid
Polybrominated biphenyl
Brominated biphenyl
Cyclohexylphenol
Biphenyl
4-halophenol
M-cresol
4-bromophenol
Toluene
Halobenzene
Bromobenzene
Phenol
Benzenoid
Aryl bromide
Monocyclic benzene moiety
Aryl halide
Organooxygen compound
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	9.45	ChemAxon
pKa (Strongest Acidic)	8.98	ChemAxon
pKa (Strongest Basic)	-6	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	2	ChemAxon
Refractivity	146.95 m³·mol⁻¹	ChemAxon
Polarizability	58.01 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163022028

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol (NP0205295)

MOL for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

3D MOL for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

3D SDF for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

3D-SDF for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

PDB for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

3D PDB for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

SMILES for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

INCHI for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

Structure for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)

3D Structure for NP0205295 (5,5'-dibromo-3-[(1s,2r,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-3'-[(1s,2s,5r)-1,2-dimethylbicyclo[3.1.0]hexan-2-yl]-6,6'-dimethyl-[1,1'-biphenyl]-2,2'-diol)