NP-MRD: Showing NP-Card for (-)-alpha-bromocuparene (NP0025122)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-19 17:19:17 UTC

Updated at

2021-06-29 23:49:51 UTC

NP-MRD ID

NP0025122

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-alpha-bromocuparene

Provided By

JEOL Database JEOL Logo

Description

Bromocuparene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (-)-alpha-bromocuparene is found in Aplysia punctata, Laurencia dendroidea and Laurencia microcladia. (-)-alpha-bromocuparene was first documented in 2018 (PMID: 29561818). Based on a literature review very few articles have been published on Bromocuparene.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119193D          

 37 38  0  0  0  0            999 V2000
    0.7120   -4.5795    3.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -3.4431    2.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.2275    3.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -1.1539    2.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -1.2519    1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.0794    0.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -0.6422   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2923    1.0043    0.6231 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5077    2.0599    1.4141 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0430    1.6470    1.3191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1210    3.1966    1.4013 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0673    0.7869    0.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0735    1.6428   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -0.0330    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5816   -2.4837    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504   -3.5582    1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -4.5650    4.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803   -5.5427    3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -4.5106    4.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -2.1014    4.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -0.2406    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    0.1505   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -1.2236   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -1.2901   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    0.5996    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    1.5083   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352    2.1000    2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0516    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    1.0648    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    2.3063   -1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    2.2684   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836    1.0082   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    0.6141   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.7580   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5245   -0.5731    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -2.6315   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -4.4856    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8  6  1  0  0  0  0
 12 10  1  0  0  0  0
 12 13  1  6  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  2 16  1  0  0  0  0
 16 15  2  0  0  0  0
 10 29  1  1  0  0  0
  6 12  1  0  0  0  0
 12 14  1  0  0  0  0
 15  5  1  0  0  0  0
  6  7  1  6  0  0  0
  4  3  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 15 36  1  0  0  0  0
  4 21  1  0  0  0  0
  3 20  1  0  0  0  0
 16 37  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  8 25  1  0  0  0  0
  8 26  1  0  0  0  0
 13 30  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    0.7120   -4.5795    3.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -3.4431    2.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.2275    3.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -1.1539    2.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -1.2519    1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.0794    0.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -0.6422   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2923    1.0043    0.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077    2.0599    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    1.6470    1.3191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1210    3.1966    1.4013 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0673    0.7869    0.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0735    1.6428   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -0.0330    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5816   -2.4837    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504   -3.5582    1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -4.5650    4.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803   -5.5427    3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -4.5106    4.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -2.1014    4.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -0.2406    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    0.1505   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -1.2236   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -1.2901   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    0.5996    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    1.5083   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352    2.1000    2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0516    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    1.0648    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    2.3063   -1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    2.2684   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836    1.0082   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    0.6141   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.7580   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5245   -0.5731    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -2.6315   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -4.4856    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
 12 10  1  0
 12 13  1  6
  3  2  2  0
  5  4  2  0
  2 16  1  0
 16 15  2  0
 10 29  1  1
  6 12  1  0
 12 14  1  0
 15  5  1  0
  6  7  1  6
  4  3  1  0
  2  1  1  0
 10 11  1  0
  6  5  1  0
 15 36  1  0
  4 21  1  0
  3 20  1  0
 16 37  1  0
  9 27  1  0
  9 28  1  0
  8 25  1  0
  8 26  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
M  END


  Mrv1652306192119193D          

 37 38  0  0  0  0            999 V2000
    0.7120   -4.5795    3.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -3.4431    2.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.2275    3.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -1.1539    2.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -1.2519    1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.0794    0.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -0.6422   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2923    1.0043    0.6231 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5077    2.0599    1.4141 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0430    1.6470    1.3191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1210    3.1966    1.4013 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0673    0.7869    0.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0735    1.6428   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -0.0330    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5816   -2.4837    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504   -3.5582    1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -4.5650    4.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803   -5.5427    3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -4.5106    4.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -2.1014    4.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -0.2406    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    0.1505   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -1.2236   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -1.2901   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    0.5996    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    1.5083   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352    2.1000    2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0516    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    1.0648    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    2.3063   -1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    2.2684   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836    1.0082   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    0.6141   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.7580   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5245   -0.5731    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -2.6315   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -4.4856    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
  9  8  1  0  0  0  0
  8  6  1  0  0  0  0
 12 10  1  0  0  0  0
 12 13  1  6  0  0  0
  3  2  2  0  0  0  0
  5  4  2  0  0  0  0
  2 16  1  0  0  0  0
 16 15  2  0  0  0  0
 10 29  1  1  0  0  0
  6 12  1  0  0  0  0
 12 14  1  0  0  0  0
 15  5  1  0  0  0  0
  6  7  1  6  0  0  0
  4  3  1  0  0  0  0
  2  1  1  0  0  0  0
 10 11  1  0  0  0  0
  6  5  1  0  0  0  0
 15 36  1  0  0  0  0
  4 21  1  0  0  0  0
  3 20  1  0  0  0  0
 16 37  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  8 25  1  0  0  0  0
  8 26  1  0  0  0  0
 13 30  1  0  0  0  0
 13 31  1  0  0  0  0
 13 32  1  0  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
  7 22  1  0  0  0  0
  7 23  1  0  0  0  0
  7 24  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025122

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(Br)C1(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H21Br/c1-11-5-7-12(8-6-11)15(4)10-9-13(16)14(15,2)3/h5-8,13H,9-10H2,1-4H3/t13-,15+/m1/s1

> <INCHI_KEY>
KORKIDZADLJCNH-HIFRSBDPSA-N

> <FORMULA>
C15H21Br

> <MOLECULAR_WEIGHT>
281.237

> <EXACT_MASS>
280.082664

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.691256554463024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-[(1S,3R)-3-bromo-1,2,2-trimethylcyclopentyl]-4-methylbenzene

> <ALOGPS_LOGP>
5.95

> <JCHEM_LOGP>
5.353477171333333

> <ALOGPS_LOGS>
-6.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
73.7386

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.14e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-[(1S,3R)-3-bromo-1,2,2-trimethylcyclopentyl]-4-methylbenzene

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    0.7120   -4.5795    3.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -3.4431    2.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.2275    3.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -1.1539    2.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -1.2519    1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.0794    0.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -0.6422   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2923    1.0043    0.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077    2.0599    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    1.6470    1.3191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1210    3.1966    1.4013 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0673    0.7869    0.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0735    1.6428   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -0.0330    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5816   -2.4837    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504   -3.5582    1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -4.5650    4.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803   -5.5427    3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -4.5106    4.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -2.1014    4.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -0.2406    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    0.1505   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -1.2236   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -1.2901   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    0.5996    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    1.5083   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352    2.1000    2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0516    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    1.0648    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    2.3063   -1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    2.2684   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836    1.0082   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    0.6141   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.7580   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5245   -0.5731    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -2.6315   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -4.4856    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
 12 10  1  0
 12 13  1  6
  3  2  2  0
  5  4  2  0
  2 16  1  0
 16 15  2  0
 10 29  1  1
  6 12  1  0
 12 14  1  0
 15  5  1  0
  6  7  1  6
  4  3  1  0
  2  1  1  0
 10 11  1  0
  6  5  1  0
 15 36  1  0
  4 21  1  0
  3 20  1  0
 16 37  1  0
  9 27  1  0
  9 28  1  0
  8 25  1  0
  8 26  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.712  -4.580   3.946  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.882  -3.443   2.983  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.420  -2.228   3.405  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.550  -1.154   2.514  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.139  -1.252   1.173  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.266  -0.079   0.161  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.771  -0.642  -1.191  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.292   1.004   0.623  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.508   2.060   1.414  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.043   1.647   1.319  0.00  0.00           C+0
HETATM   11 Br   UNK     0      -1.121   3.197   1.401  0.00  0.00          Br+0
HETATM   12  C   UNK     0      -0.067   0.787   0.040  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.074   1.643  -1.255  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.370  -0.033   0.035  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.582  -2.484   0.775  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.450  -3.558   1.663  0.00  0.00           C+0
HETATM   17  H   UNK     0       1.496  -4.565   4.710  0.00  0.00           H+0
HETATM   18  H   UNK     0       0.780  -5.543   3.429  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.263  -4.511   4.438  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.746  -2.101   4.435  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.980  -0.241   2.914  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.082   0.151  -1.881  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.001  -1.224  -1.709  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.644  -1.290  -1.047  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.134   0.600   1.195  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.745   1.508  -0.241  0.00  0.00           H+0
HETATM   27  H   UNK     0       1.835   2.100   2.459  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.698   3.052   0.987  0.00  0.00           H+0
HETATM   29  H   UNK     0      -0.233   1.065   2.206  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.794   2.306  -1.325  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.970   2.268  -1.326  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.084   1.008  -2.148  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.244   0.614  -0.098  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.377  -0.758  -0.786  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.525  -0.573   0.974  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.220  -2.632  -0.240  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.005  -4.486   1.309  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    3   16    1                                                  
CONECT    3    2    4   20                                                  
CONECT    4    5    3   21                                                  
CONECT    5    4   15    6                                                  
CONECT    6    8   12    7    5                                             
CONECT    7    6   22   23   24                                             
CONECT    8    9    6   25   26                                             
CONECT    9   10    8   27   28                                             
CONECT   10    9   12   29   11                                             
CONECT   11   10                                                            
CONECT   12   10   13    6   14                                             
CONECT   13   12   30   31   32                                             
CONECT   14   12   33   34   35                                             
CONECT   15   16    5   36                                                  
CONECT   16    2   15   37                                                  
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    3                                                            
CONECT   21    4                                                            
CONECT   22    7                                                            
CONECT   23    7                                                            
CONECT   24    7                                                            
CONECT   25    8                                                            
CONECT   26    8                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29   10                                                            
CONECT   30   13                                                            
CONECT   31   13                                                            
CONECT   32   13                                                            
CONECT   33   14                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

RDKit          3D

37 38  0  0  0  0  0  0  0  0999 V2000
    0.7120   -4.5795    3.9459 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8819   -3.4431    2.9834 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4201   -2.2275    3.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5499   -1.1539    2.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386   -1.2519    1.1733 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -0.0794    0.1610 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7710   -0.6422   -1.1912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2923    1.0043    0.6231 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5077    2.0599    1.4141 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    1.6470    1.3191 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1210    3.1966    1.4013 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0673    0.7869    0.0402 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0735    1.6428   -1.2553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3697   -0.0330    0.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5816   -2.4837    0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4504   -3.5582    1.6629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4964   -4.5650    4.7099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803   -5.5427    3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -4.5106    4.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7465   -2.1014    4.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9797   -0.2406    2.9136 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0815    0.1505   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0013   -1.2236   -1.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6442   -1.2901   -1.0467 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1341    0.5996    1.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453    1.5083   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8352    2.1000    2.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983    3.0516    0.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333    1.0648    2.2056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7939    2.3063   -1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9696    2.2684   -1.3262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0836    1.0082   -2.1483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2443    0.6141   -0.0981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -0.7580   -0.7857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5245   -0.5731    0.9744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2203   -2.6315   -0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0052   -4.4856    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
 12 10  1  0
 12 13  1  6
  3  2  2  0
  5  4  2  0
  2 16  1  0
 16 15  2  0
 10 29  1  1
  6 12  1  0
 12 14  1  0
 15  5  1  0
  6  7  1  6
  4  3  1  0
  2  1  1  0
 10 11  1  0
  6  5  1  0
 15 36  1  0
  4 21  1  0
  3 20  1  0
 16 37  1  0
  9 27  1  0
  9 28  1  0
  8 25  1  0
  8 26  1  0
 13 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 14 35  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₁Br

Average Mass

281.2370 Da

Monoisotopic Mass

280.08266 Da

IUPAC Name

1-[(1S,3R)-3-bromo-1,2,2-trimethylcyclopentyl]-4-methylbenzene

Traditional Name

1-[(1S,3R)-3-bromo-1,2,2-trimethylcyclopentyl]-4-methylbenzene

CAS Registry Number

Not Available

SMILES

[H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]([H])(Br)C1(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C15H21Br/c1-11-5-7-12(8-6-11)15(4)10-9-13(16)14(15,2)3/h5-8,13H,9-10H2,1-4H3/t13-,15+/m1/s1

InChI Key

KORKIDZADLJCNH-HIFRSBDPSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aplysia punctata	LOTUS Database	35616633
Laurencia dendroidea	LOTUS Database	35616633
Laurencia microcladia	JEOL database	Kladi, M., et al, Tetrahedron 63, 7606 (2007)

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

Cuparane sesquiterpenoid
Sesquiterpenoid
Toluene
Benzenoid
Monocyclic benzene moiety
Hydrocarbon derivative
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic 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	5.95	ALOGPS
logP	5.35	ChemAxon
logS	-6.4	ALOGPS
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	73.74 m³·mol⁻¹	ChemAxon
Polarizability	28.69 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

C00012504

Chemspider ID

10470572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23425342

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Esselin H, Tomi F, Bighelli A, Sutour S: New Metabolites Isolated from a Laurencia obtusa Population Collected in Corsica. Molecules. 2018 Mar 21;23(4). pii: molecules23040720. doi: 10.3390/molecules23040720. [PubMed:29561818 ]
Kladi, M., et al. (2007). Kladi, M., et al, Tetrahedron 63, 7606 (2007). Tetrahedron.

Showing NP-Card for (-)-alpha-bromocuparene (NP0025122)

MOL for NP0025122 ((-)-alpha-bromocuparene)

3D MOL for NP0025122 ((-)-alpha-bromocuparene)

3D SDF for NP0025122 ((-)-alpha-bromocuparene)

3D-SDF for NP0025122 ((-)-alpha-bromocuparene)

PDB for NP0025122 ((-)-alpha-bromocuparene)

3D PDB for NP0025122 ((-)-alpha-bromocuparene)

SMILES for NP0025122 ((-)-alpha-bromocuparene)

INCHI for NP0025122 ((-)-alpha-bromocuparene)

Structure for NP0025122 ((-)-alpha-bromocuparene)

3D Structure for NP0025122 ((-)-alpha-bromocuparene)