NP-MRD: Showing NP-Card for (-)-beta-macrocarpene (NP0031004)

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Record Information

Version

2.0

Created at

2021-06-19 22:12:41 UTC

Updated at

2021-06-29 23:59:19 UTC

NP-MRD ID

NP0031004

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-beta-macrocarpene

Provided By

JEOL Database JEOL Logo

Description

(S)-beta-macrocarpene is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. (-)-beta-macrocarpene is found in Cupressus macrocarpa. (-)-beta-macrocarpene was first documented in 2008 (PMID: 18524777). Based on a literature review a small amount of articles have been published on (S)-beta-macrocarpene (PMID: 33385084) (PMID: 26471326).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100123D          

 39 40  0  0  0  0            999 V2000
   -1.8569   -2.2293   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780   -1.2985   -0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517   -1.4651   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.5804   -0.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8560    0.3255    0.9717 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8447    1.3801    1.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    1.2776    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855    2.2771    3.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4699    3.5735    2.4285 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4364    3.3342    0.9050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4270    4.6909    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848    2.5540    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    2.5532    0.5444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4687    0.9308    0.4829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4766   -0.1658    0.1231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5051   -2.6887   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -3.0356   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -1.6822   -2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506   -2.2810   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    0.0094   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384   -1.2130    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056   -0.3240    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.4235    3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752    1.8088    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    2.5189    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230    4.2145    2.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763    4.1207    2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    4.5567   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    5.2673    0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    5.2963    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    3.0830    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353    1.5504    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6925    2.4359   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    2.2134   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    3.2327    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    1.5554   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    1.5832    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    0.2929   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -0.5796    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  6  7  2  0  0  0  0
  5 14  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2 15  1  0  0  0  0
 15 14  1  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
 10 11  1  6  0  0  0
  5  4  1  0  0  0  0
 10 12  1  0  0  0  0
  8  9  1  0  0  0  0
  5 22  1  1  0  0  0
  6 13  1  0  0  0  0
  8 24  1  0  0  0  0
  8 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
  7 23  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  3 19  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
M  END

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.8569   -2.2293   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780   -1.2985   -0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517   -1.4651   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.5804   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8560    0.3255    0.9717 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8447    1.3801    1.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    1.2776    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855    2.2771    3.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699    3.5735    2.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364    3.3342    0.9050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4270    4.6909    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848    2.5540    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    2.5532    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687    0.9308    0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4766   -0.1658    0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051   -2.6887   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -3.0356   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -1.6822   -2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506   -2.2810   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    0.0094   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384   -1.2130    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056   -0.3240    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.4235    3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752    1.8088    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    2.5189    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230    4.2145    2.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763    4.1207    2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    4.5567   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    5.2673    0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    5.2963    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    3.0830    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353    1.5504    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6925    2.4359   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    2.2134   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    3.2327    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    1.5554   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    1.5832    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    0.2929   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -0.5796    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  9 10  1  0
 10 13  1  0
  6  7  2  0
  5 14  1  0
  4  3  1  0
  3  2  2  0
  2 15  1  0
 15 14  1  0
  2  1  1  0
  6  5  1  0
 10 11  1  6
  5  4  1  0
 10 12  1  0
  8  9  1  0
  5 22  1  1
  6 13  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 13 34  1  0
 13 35  1  0
  7 23  1  0
  4 20  1  0
  4 21  1  0
  3 19  1  0
 15 38  1  0
 15 39  1  0
 14 36  1  0
 14 37  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
M  END


  Mrv1652306202100123D          

 39 40  0  0  0  0            999 V2000
   -1.8569   -2.2293   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780   -1.2985   -0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517   -1.4651   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.5804   -0.1178 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8560    0.3255    0.9717 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8447    1.3801    1.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    1.2776    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855    2.2771    3.2365 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4699    3.5735    2.4285 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4364    3.3342    0.9050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4270    4.6909    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848    2.5540    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    2.5532    0.5444 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4687    0.9308    0.4829 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4766   -0.1658    0.1231 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5051   -2.6887   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -3.0356   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -1.6822   -2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506   -2.2810   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    0.0094   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384   -1.2130    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056   -0.3240    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.4235    3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752    1.8088    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    2.5189    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230    4.2145    2.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763    4.1207    2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    4.5567   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    5.2673    0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    5.2963    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    3.0830    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353    1.5504    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6925    2.4359   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    2.2134   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    3.2327    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    1.5554   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    1.5832    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    0.2929   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -0.5796    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  6  7  2  0  0  0  0
  5 14  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  2  0  0  0  0
  2 15  1  0  0  0  0
 15 14  1  0  0  0  0
  2  1  1  0  0  0  0
  6  5  1  0  0  0  0
 10 11  1  6  0  0  0
  5  4  1  0  0  0  0
 10 12  1  0  0  0  0
  8  9  1  0  0  0  0
  5 22  1  1  0  0  0
  6 13  1  0  0  0  0
  8 24  1  0  0  0  0
  8 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 13 34  1  0  0  0  0
 13 35  1  0  0  0  0
  7 23  1  0  0  0  0
  4 20  1  0  0  0  0
  4 21  1  0  0  0  0
  3 19  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 14 36  1  0  0  0  0
 14 37  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
 12 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031004

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(C2=C([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C2([H])[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-12-6-8-13(9-7-12)14-5-4-10-15(2,3)11-14/h5-6,13H,4,7-11H2,1-3H3/t13-/m1/s1

> <INCHI_KEY>
BKRLNEMLMVJATK-CYBMUJFWSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.61212462784158

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S)-4',5,5-trimethyl-[1,1'-bi(cyclohexane)]-1,3'-diene

> <ALOGPS_LOGP>
6.20

> <JCHEM_LOGP>
4.61892529

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
68.5773

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-β-macrocarpene

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.8569   -2.2293   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780   -1.2985   -0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517   -1.4651   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.5804   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8560    0.3255    0.9717 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8447    1.3801    1.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    1.2776    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855    2.2771    3.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699    3.5735    2.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364    3.3342    0.9050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4270    4.6909    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848    2.5540    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    2.5532    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687    0.9308    0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4766   -0.1658    0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051   -2.6887   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -3.0356   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -1.6822   -2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506   -2.2810   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    0.0094   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384   -1.2130    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056   -0.3240    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.4235    3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752    1.8088    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    2.5189    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230    4.2145    2.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763    4.1207    2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    4.5567   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    5.2673    0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    5.2963    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    3.0830    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353    1.5504    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6925    2.4359   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    2.2134   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    3.2327    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    1.5554   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    1.5832    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    0.2929   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -0.5796    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
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 12 32  1  0
 12 33  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.857  -2.229  -1.331  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.878  -1.299  -0.675  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.452  -1.465  -0.789  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.466  -0.580  -0.118  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.856   0.326   0.972  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.845   1.380   1.457  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.420   1.278   2.671  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.385   2.277   3.236  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.470   3.574   2.429  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.436   3.334   0.905  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.427   4.691   0.178  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.685   2.554   0.445  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.147   2.553   0.544  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.469   0.931   0.483  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.477  -0.166   0.123  0.00  0.00           C+0
HETATM   16  H   UNK     0      -2.505  -2.689  -0.577  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.357  -3.036  -1.877  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.483  -1.682  -2.042  0.00  0.00           H+0
HETATM   19  H   UNK     0       0.851  -2.281  -1.388  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.962   0.009  -0.897  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.238  -1.213   0.337  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.606  -0.324   1.825  0.00  0.00           H+0
HETATM   23  H   UNK     0       2.199   0.424   3.307  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.375   1.809   3.294  0.00  0.00           H+0
HETATM   25  H   UNK     0       3.092   2.519   4.265  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.623   4.215   2.711  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.376   4.121   2.716  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.379   4.557  -0.909  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.331   5.267   0.405  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.564   5.296   0.476  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.602   3.083   0.727  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.735   1.550   0.878  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.692   2.436  -0.645  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.221   2.213  -0.495  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.285   3.233   0.588  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.296   1.555  -0.404  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.903   1.583   1.250  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.298   0.293  -0.440  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.908  -0.580   1.043  0.00  0.00           H+0
CONECT    1    2   16   17   18                                             
CONECT    2    3   15    1                                                  
CONECT    3    4    2   19                                                  
CONECT    4    3    5   20   21                                             
CONECT    5   14    6    4   22                                             
CONECT    6    7    5   13                                                  
CONECT    7    8    6   23                                                  
CONECT    8    7    9   24   25                                             
CONECT    9   10    8   26   27                                             
CONECT   10    9   13   11   12                                             
CONECT   11   10   28   29   30                                             
CONECT   12   10   31   32   33                                             
CONECT   13   10    6   34   35                                             
CONECT   14    5   15   36   37                                             
CONECT   15    2   14   38   39                                             
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    3                                                            
CONECT   20    4                                                            
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    7                                                            
CONECT   24    8                                                            
CONECT   25    8                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28   11                                                            
CONECT   29   11                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   12                                                            
CONECT   34   13                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

RDKit          3D

39 40  0  0  0  0  0  0  0  0999 V2000
   -1.8569   -2.2293   -1.3305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780   -1.2985   -0.6750 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4517   -1.4651   -0.7893 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -0.5804   -0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8560    0.3255    0.9717 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8447    1.3801    1.4569 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4203    1.2776    2.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3855    2.2771    3.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4699    3.5735    2.4285 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364    3.3342    0.9050 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4270    4.6909    0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6848    2.5540    0.4451 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1468    2.5532    0.5444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4687    0.9308    0.4829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4766   -0.1658    0.1231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5051   -2.6887   -0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3565   -3.0356   -1.8768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4833   -1.6822   -2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506   -2.2810   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9617    0.0094   -0.8973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2384   -1.2130    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056   -0.3240    1.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.4235    3.3074 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3752    1.8088    3.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0925    2.5189    4.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6230    4.2145    2.7110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3763    4.1207    2.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3788    4.5567   -0.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3308    5.2673    0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5638    5.2963    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6024    3.0830    0.7267 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7353    1.5504    0.8784 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6925    2.4359   -0.6447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2212    2.2134   -0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2850    3.2327    0.5882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2962    1.5554   -0.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9029    1.5832    1.2504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    0.2929   -0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -0.5796    1.0428 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  9 10  1  0
 10 13  1  0
  6  7  2  0
  5 14  1  0
  4  3  1  0
  3  2  2  0
  2 15  1  0
 15 14  1  0
  2  1  1  0
  6  5  1  0
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  5  4  1  0
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  8  9  1  0
  5 22  1  1
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  8 25  1  0
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  7 23  1  0
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  1 16  1  0
  1 17  1  0
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 12 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
(-)-beta-Macrocarpene	ChEBI
(1's)-4',5,5-Trimethyl-1,1'-bi(cyclohexane)-1,3'-diene	Kegg
(-)-b-Macrocarpene	Generator
(-)-Β-macrocarpene	Generator
(S)-b-Macrocarpene	Generator
(S)-Β-macrocarpene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1'S)-4',5,5-trimethyl-[1,1'-bi(cyclohexane)]-1,3'-diene

Traditional Name

(-)-β-macrocarpene

CAS Registry Number

Not Available

SMILES

[H]C1=C(C([H])([H])[H])C([H])([H])C([H])([H])[C@]([H])(C2=C([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C2([H])[H])C1([H])[H]

InChI Identifier

InChI=1S/C15H24/c1-12-6-8-13(9-7-12)14-5-4-10-15(2,3)11-14/h5-6,13H,4,7-11H2,1-3H3/t13-/m1/s1

InChI Key

BKRLNEMLMVJATK-CYBMUJFWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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
Hesperocyparis macrocarpa	JEOL database	Cool, L. G., Phytochemistry 66, 249 (2005)

Chemical Taxonomy

Classification

Not classified

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	6.2	ALOGPS
logP	4.62	ChemAxon
logS	-4.4	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	68.58 m³·mol⁻¹	ChemAxon
Polarizability	26.61 Å³	ChemAxon
Number of Rings	2	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

26332204

KEGG Compound ID

C19752

BioCyc ID

CPD-12759

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

61344

Good Scents ID

Not Available

References

General References

Kollner TG, Schnee C, Li S, Svatos A, Schneider B, Gershenzon J, Degenhardt J: Protonation of a neutral (S)-beta-bisabolene intermediate is involved in (S)-beta-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11. J Biol Chem. 2008 Jul 25;283(30):20779-88. doi: 10.1074/jbc.M802682200. Epub 2008 Jun 3. [PubMed:18524777 ]
Ossipov V, Koivuniemi A, Mizina P, Salminen JP: UPLC-PDA-Q Exactive Orbitrap-MS profiling of the lipophilic compounds product isolated from Eucalyptus viminalis plants. Heliyon. 2020 Dec 23;6(12):e05768. doi: 10.1016/j.heliyon.2020.e05768. eCollection 2020 Dec. [PubMed:33385084 ]
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Showing NP-Card for (-)-beta-macrocarpene (NP0031004)

MOL for NP0031004 ((-)-beta-macrocarpene)

3D MOL for NP0031004 ((-)-beta-macrocarpene)

3D SDF for NP0031004 ((-)-beta-macrocarpene)

3D-SDF for NP0031004 ((-)-beta-macrocarpene)

PDB for NP0031004 ((-)-beta-macrocarpene)

3D PDB for NP0031004 ((-)-beta-macrocarpene)

SMILES for NP0031004 ((-)-beta-macrocarpene)

INCHI for NP0031004 ((-)-beta-macrocarpene)

Structure for NP0031004 ((-)-beta-macrocarpene)

3D Structure for NP0031004 ((-)-beta-macrocarpene)