NP-MRD: Showing NP-Card for (1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol (NP0241098)

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Record Information

Version

2.0

Created at

2022-09-07 01:05:01 UTC

Updated at

2022-09-07 01:05:01 UTC

NP-MRD ID

NP0241098

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol

Description

(1R,3S,5S)-1-[(1S,4S)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]Hexan-3-ol 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. (1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol is found in Laurencia obtusa. Based on a literature review very few articles have been published on (1R,3S,5S)-1-[(1S,4S)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]Hexan-3-ol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -3.6075   -0.3017    0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621    0.4372   -0.1819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1714    1.8053   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2872    0.6523    0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2234   -0.2912    0.0912 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0168   -0.2607    0.9273 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0908    0.3671    2.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6079    1.1288    1.1024 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0303    1.0671    0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9777   -0.0928   -0.3531 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3460   -0.5753   -0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3575    0.3710   -1.4880 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1680   -1.0900    0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8157   -1.6524   -0.0861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6839   -1.5949   -1.3510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3834   -0.2788   -1.4874 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5740    0.8510   -2.8377 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.7827   -1.3322    0.2171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3343   -0.3988    1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5987    0.1938    0.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4633    2.2866   -1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1830    1.7089   -0.9391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1465    2.4161    0.4199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9245    1.6882    0.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4948    0.5494    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0760    0.0652   -0.9382 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2099    0.7492    2.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8688   -0.0289    2.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0520    2.0090    0.7694 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6616    0.7698    1.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3703    1.9893    0.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9651    0.3437   -0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2709   -1.1000   -1.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8249   -1.2070    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0773    1.3199   -1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7703   -1.3834    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8911   -1.9777   -0.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0838   -2.4567   -0.2693 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641   -1.9603    0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3879   -2.4605   -1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389   -1.8192   -2.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4223   -0.5065   -1.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  0
 10 12  1  6
 10  9  1  0
  9  8  1  0
  8  7  1  0
  6  7  1  1
  6 13  1  0
  6  5  1  0
  5 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16  2  1  0
  2  1  1  0
  2  3  1  0
  2  4  1  0
 13 10  1  0
  4  5  1  0
  6  8  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
  9 30  1  0
  9 31  1  0
  8 29  1  6
  7 27  1  0
  7 28  1  0
 13 36  1  0
 13 37  1  0
  5 26  1  6
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  6
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
M  END


  Mrv1652309072203052D          

 17 19  0  0  1  0            999 V2000
   -1.6187   -1.8987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347   -2.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5078   -2.9535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5992   -1.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2213   -1.5201    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5569   -0.7665    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1576   -0.3540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.0585    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3415    0.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8264   -0.3540    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4395    0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4395   -0.9060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3415   -1.0214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3707   -2.9413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4498   -3.0275    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7854   -3.7812    0.0000 Br  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  1  0  0  0
  6  7  1  1  0  0  0
  8  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  6  0  0  0
 10 13  1  0  0  0  0
  6 13  1  0  0  0  0
  5 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
 16 17  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0241098

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]1(O)C[C@@H]2C[C@@]2(C1)[C@H]1CC[C@H](Br)C(C)(C)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H25BrO/c1-13(2)6-10(4-5-12(13)16)15-8-11(15)7-14(3,17)9-15/h10-12,17H,4-9H2,1-3H3/t10-,11+,12-,14-,15+/m0/s1

> <INCHI_KEY>
DFPDSQVEWPQCNC-CUZKYEQNSA-N

> <FORMULA>
C15H25BrO

> <MOLECULAR_WEIGHT>
301.268

> <EXACT_MASS>
300.108878

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
30.883147785775584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,5S)-1-[(1S,4S)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol

> <JCHEM_LOGP>
3.5804023330000003

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.891337339739284

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0967290475980374

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
74.20589999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5S)-1-[(1S,4S)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.022  -3.544   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.745  -4.405   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.815  -5.513   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.118  -2.999   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.413  -2.838   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.039  -1.431   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.294  -0.661   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.039   0.109   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.504   0.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.409  -0.661   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.554   0.370   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.554  -1.691   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.504  -1.907   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.318  -4.083   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.692  -5.490   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.840  -5.651   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0      -1.466  -7.058   0.000  0.00  0.00          Br+0
CONECT    1    2                                                            
CONECT    2    1    3    4   16                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7    8   13                                             
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    6                                                       
CONECT   14    5   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₅BrO

Average Mass

301.2680 Da

Monoisotopic Mass

300.10888 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@]1(O)C[C@@H]2C[C@@]2(C1)[C@H]1CC[C@H](Br)C(C)(C)C1

InChI Identifier

InChI=1S/C15H25BrO/c1-13(2)6-10(4-5-12(13)16)15-8-11(15)7-14(3,17)9-15/h10-12,17H,4-9H2,1-3H3/t10-,11+,12-,14-,15+/m0/s1

InChI Key

DFPDSQVEWPQCNC-CUZKYEQNSA-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 obtusa	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
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Alkyl bromide
Alcohol
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

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

163038557

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol (NP0241098)

MOL for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

3D MOL for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

3D SDF for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

3D-SDF for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

PDB for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

3D PDB for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

SMILES for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

INCHI for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

Structure for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)

3D Structure for NP0241098 ((1r,3s,5s)-1-[(1s,4s)-4-bromo-3,3-dimethylcyclohexyl]-3-methylbicyclo[3.1.0]hexan-3-ol)