NP-MRD: Showing NP-Card for oculiferane (NP0042891)

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Record Information

Version

2.0

Created at

2021-06-21 00:26:32 UTC

Updated at

2021-06-30 00:18:16 UTC

NP-MRD ID

NP0042891

Secondary Accession Numbers

None

Natural Product Identification

Common Name

oculiferane

Provided By

JEOL Database JEOL Logo

Description

1-(1,2,2-Trimethyl-3beta-bromocyclopentane-1beta-yl)-3alpha-chloro-4beta-bromo-4-methylcyclohexane-1beta-ol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. oculiferane is found in Aplysia oculifera. oculiferane was first documented in 2014 (Hegazy, M.-E. F., et al.). Based on a literature review very few articles have been published on 1-(1,2,2-Trimethyl-3beta-bromocyclopentane-1beta-yl)-3alpha-chloro-4beta-bromo-4-methylcyclohexane-1beta-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102263D          

 44 45  0  0  0  0            999 V2000
   -0.3595    2.9768    1.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    2.0032    1.1620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0481    0.6065    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    2.0023    1.9417 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9904    1.0147    3.6135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    1.4748    0.9819 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4567    1.7063   -0.4248 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1015    2.4778   -0.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4494    4.0001   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.1618   -1.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0962    0.7527   -1.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402    2.8179   -1.4524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1320    2.5369   -2.6701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4757    2.9434   -4.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4634    4.4708   -4.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.2384   -5.4378 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.2716   -4.1206 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8067    2.7624   -5.6034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    2.5720   -2.9050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2904    3.1074    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    2.6086    2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800    3.9687    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.2733    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.1574    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.6117    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2310    3.0165    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.4073    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    2.0029    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1835    2.2497   -1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    0.7263   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    4.2770    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    4.6242   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9975    4.3033   -1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.2848   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    2.4162   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    3.8999   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    3.0579   -2.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    1.4661   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    4.9509   -3.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    4.7826   -5.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    4.8913   -4.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101    1.1854   -4.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    2.0267   -3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    3.6387   -2.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
 10  8  1  0  0  0  0
 13 12  1  0  0  0  0
  2  1  1  1  0  0  0
 12 10  1  0  0  0  0
 17 18  1  0  0  0  0
  8  2  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  6  0  0  0
 19 17  1  0  0  0  0
  2  3  1  0  0  0  0
 19 10  1  0  0  0  0
  4  5  1  0  0  0  0
 17 14  1  0  0  0  0
 10 11  1  6  0  0  0
 14 13  1  0  0  0  0
  8  9  1  1  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 17 42  1  6  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
 12 35  1  0  0  0  0
 12 36  1  0  0  0  0
  4 26  1  1  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 11 34  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
M  END

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.3595    2.9768    1.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    2.0032    1.1620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0481    0.6065    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    2.0023    1.9417 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9904    1.0147    3.6135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    1.4748    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567    1.7063   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015    2.4778   -0.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4494    4.0001   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.1618   -1.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0962    0.7527   -1.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402    2.8179   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1320    2.5369   -2.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757    2.9434   -4.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4634    4.4708   -4.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.2384   -5.4378 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.2716   -4.1206 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8067    2.7624   -5.6034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    2.5720   -2.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    3.1074    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    2.6086    2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800    3.9687    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.2733    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.1574    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.6117    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2310    3.0165    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.4073    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    2.0029    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1835    2.2497   -1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    0.7263   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    4.2770    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    4.6242   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9975    4.3033   -1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.2848   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    2.4162   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    3.8999   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    3.0579   -2.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    1.4661   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    4.9509   -3.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    4.7826   -5.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    4.8913   -4.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101    1.1854   -4.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    2.0267   -3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    3.6387   -2.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
 10  8  1  0
 13 12  1  0
  2  1  1  1
 12 10  1  0
 17 18  1  0
  8  2  1  0
 14 15  1  0
 14 16  1  6
 19 17  1  0
  2  3  1  0
 19 10  1  0
  4  5  1  0
 17 14  1  0
 10 11  1  6
 14 13  1  0
  8  9  1  1
 19 43  1  0
 19 44  1  0
 17 42  1  6
 13 37  1  0
 13 38  1  0
 12 35  1  0
 12 36  1  0
  4 26  1  1
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 11 34  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
M  END


  Mrv1652306212102263D          

 44 45  0  0  0  0            999 V2000
   -0.3595    2.9768    1.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    2.0032    1.1620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0481    0.6065    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    2.0023    1.9417 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9904    1.0147    3.6135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    1.4748    0.9819 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4567    1.7063   -0.4248 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1015    2.4778   -0.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4494    4.0001   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.1618   -1.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0962    0.7527   -1.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402    2.8179   -1.4524 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1320    2.5369   -2.6701 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4757    2.9434   -4.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4634    4.4708   -4.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.2384   -5.4378 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.2716   -4.1206 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8067    2.7624   -5.6034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    2.5720   -2.9050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2904    3.1074    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    2.6086    2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800    3.9687    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.2733    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.1574    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.6117    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2310    3.0165    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.4073    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    2.0029    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1835    2.2497   -1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    0.7263   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    4.2770    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    4.6242   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9975    4.3033   -1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.2848   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    2.4162   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    3.8999   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    3.0579   -2.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    1.4661   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    4.9509   -3.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    4.7826   -5.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    4.8913   -4.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101    1.1854   -4.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    2.0267   -3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    3.6387   -2.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
 10  8  1  0  0  0  0
 13 12  1  0  0  0  0
  2  1  1  1  0  0  0
 12 10  1  0  0  0  0
 17 18  1  0  0  0  0
  8  2  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  6  0  0  0
 19 17  1  0  0  0  0
  2  3  1  0  0  0  0
 19 10  1  0  0  0  0
  4  5  1  0  0  0  0
 17 14  1  0  0  0  0
 10 11  1  6  0  0  0
 14 13  1  0  0  0  0
  8  9  1  1  0  0  0
 19 43  1  0  0  0  0
 19 44  1  0  0  0  0
 17 42  1  6  0  0  0
 13 37  1  0  0  0  0
 13 38  1  0  0  0  0
 12 35  1  0  0  0  0
 12 36  1  0  0  0  0
  4 26  1  1  0  0  0
  6 27  1  0  0  0  0
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  7 30  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
  3 23  1  0  0  0  0
  3 24  1  0  0  0  0
  3 25  1  0  0  0  0
 11 34  1  0  0  0  0
  9 31  1  0  0  0  0
  9 32  1  0  0  0  0
  9 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042891

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1(C([H])([H])C([H])([H])[C@@](Br)(C([H])([H])[H])[C@@]([H])(Cl)C1([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/C15H25Br2ClO/c1-12(2)10(16)5-6-14(12,4)15(19)8-7-13(3,17)11(18)9-15/h10-11,19H,5-9H2,1-4H3/t10-,11-,13-,14+,15+/m0/s1

> <INCHI_KEY>
RITYTGBWLLRFSG-XSXPHNMFSA-N

> <FORMULA>
C15H25Br2ClO

> <MOLECULAR_WEIGHT>
416.62

> <EXACT_MASS>
413.996069

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.62824133058909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
4.789359401

> <ALOGPS_LOGS>
-6.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.297664027661348

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1060017543009257

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
87.99199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.10e-04 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 44 45  0  0  0  0  0  0  0  0999 V2000
   -0.3595    2.9768    1.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    2.0032    1.1620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0481    0.6065    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    2.0023    1.9417 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9904    1.0147    3.6135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    1.4748    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567    1.7063   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015    2.4778   -0.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4494    4.0001   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.1618   -1.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0962    0.7527   -1.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402    2.8179   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1320    2.5369   -2.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757    2.9434   -4.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4634    4.4708   -4.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.2384   -5.4378 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.2716   -4.1206 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8067    2.7624   -5.6034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    2.5720   -2.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    3.1074    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    2.6086    2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800    3.9687    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.2733    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.1574    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.6117    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2310    3.0165    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.4073    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    2.0029    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1835    2.2497   -1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    0.7263   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    4.2770    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    4.6242   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9975    4.3033   -1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.2848   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    2.4162   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    3.8999   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    3.0579   -2.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    1.4661   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    4.9509   -3.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    4.7826   -5.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    4.8913   -4.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101    1.1854   -4.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    2.0267   -3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    3.6387   -2.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
 10  8  1  0
 13 12  1  0
  2  1  1  1
 12 10  1  0
 17 18  1  0
  8  2  1  0
 14 15  1  0
 14 16  1  6
 19 17  1  0
  2  3  1  0
 19 10  1  0
  4  5  1  0
 17 14  1  0
 10 11  1  6
 14 13  1  0
  8  9  1  1
 19 43  1  0
 19 44  1  0
 17 42  1  6
 13 37  1  0
 13 38  1  0
 12 35  1  0
 12 36  1  0
  4 26  1  1
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 11 34  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.360   2.977   1.861  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.613   2.003   1.162  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.048   0.607   1.150  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.958   2.002   1.942  0.00  0.00           C+0
HETATM    5 Br   UNK     0       1.990   1.015   3.614  0.00  0.00          Br+0
HETATM    6  C   UNK     0       3.009   1.475   0.982  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.457   1.706  -0.425  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.101   2.478  -0.296  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.449   4.000  -0.280  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.156   2.162  -1.555  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.096   0.753  -1.654  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.240   2.818  -1.452  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.132   2.537  -2.670  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.476   2.943  -4.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.463   4.471  -4.158  0.00  0.00           C+0
HETATM   16 Br   UNK     0      -2.661   2.238  -5.438  0.00  0.00          Br+0
HETATM   17  C   UNK     0      -0.091   2.272  -4.121  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       0.807   2.762  -5.603  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       0.805   2.572  -2.905  0.00  0.00           C+0
HETATM   20  H   UNK     0      -1.290   3.107   1.308  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.634   2.609   2.857  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.080   3.969   2.007  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.321   0.273   2.156  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.607  -0.157   0.720  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.989   0.612   0.592  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.231   3.017   2.253  0.00  0.00           H+0
HETATM   27  H   UNK     0       3.217   0.407   1.122  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.959   2.003   1.120  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.184   2.250  -1.040  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.333   0.726  -0.894  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.097   4.277   0.556  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.555   4.624  -0.211  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.998   4.303  -1.177  0.00  0.00           H+0
HETATM   34  H   UNK     0       0.716   0.285  -1.911  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.782   2.416  -0.592  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.160   3.900  -1.314  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.089   3.058  -2.536  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.378   1.466  -2.681  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.801   4.951  -3.431  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.139   4.783  -5.157  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.465   4.891  -4.010  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.210   1.185  -4.211  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.748   2.027  -3.037  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.048   3.639  -2.907  0.00  0.00           H+0
CONECT    1    2   20   21   22                                             
CONECT    2    4    1    8    3                                             
CONECT    3    2   23   24   25                                             
CONECT    4    2    6    5   26                                             
CONECT    5    4                                                            
CONECT    6    4    7   27   28                                             
CONECT    7    6    8   29   30                                             
CONECT    8    7   10    2    9                                             
CONECT    9    8   31   32   33                                             
CONECT   10    8   12   19   11                                             
CONECT   11   10   34                                                       
CONECT   12   13   10   35   36                                             
CONECT   13   12   14   37   38                                             
CONECT   14   15   16   17   13                                             
CONECT   15   14   39   40   41                                             
CONECT   16   14                                                            
CONECT   17   18   19   14   42                                             
CONECT   18   17                                                            
CONECT   19   17   10   43   44                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    1                                                            
CONECT   23    3                                                            
CONECT   24    3                                                            
CONECT   25    3                                                            
CONECT   26    4                                                            
CONECT   27    6                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    7                                                            
CONECT   31    9                                                            
CONECT   32    9                                                            
CONECT   33    9                                                            
CONECT   34   11                                                            
CONECT   35   12                                                            
CONECT   36   12                                                            
CONECT   37   13                                                            
CONECT   38   13                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   15                                                            
CONECT   42   17                                                            
CONECT   43   19                                                            
CONECT   44   19                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   90    0
END

RDKit          3D

44 45  0  0  0  0  0  0  0  0999 V2000
   -0.3595    2.9768    1.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6128    2.0032    1.1620 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0481    0.6065    1.1497 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9577    2.0023    1.9417 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9904    1.0147    3.6135 Br  0  0  0  0  0  0  0  0  0  0  0  0
    3.0090    1.4748    0.9819 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4567    1.7063   -0.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1015    2.4778   -0.2957 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4494    4.0001   -0.2800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1556    2.1618   -1.5554 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0962    0.7527   -1.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2402    2.8179   -1.4524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1320    2.5369   -2.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757    2.9434   -4.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4634    4.4708   -4.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6613    2.2384   -5.4378 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.0908    2.2716   -4.1206 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8067    2.7624   -5.6034 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.8047    2.5720   -2.9050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    3.1074    1.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6338    2.6086    2.8566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0800    3.9687    2.0069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3209    0.2733    2.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.1574    0.7196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9890    0.6117    0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2310    3.0165    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2166    0.4073    1.1218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595    2.0029    1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1835    2.2497   -1.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3334    0.7263   -0.8940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    4.2770    0.5563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    4.6242   -0.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9975    4.3033   -1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    0.2848   -1.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7816    2.4162   -0.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1596    3.8999   -1.3141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    3.0579   -2.5364 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3779    1.4661   -2.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010    4.9509   -3.4312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1389    4.7826   -5.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    4.8913   -4.0097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2101    1.1854   -4.2114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7478    2.0267   -3.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    3.6387   -2.9070 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
 10  8  1  0
 13 12  1  0
  2  1  1  1
 12 10  1  0
 17 18  1  0
  8  2  1  0
 14 15  1  0
 14 16  1  6
 19 17  1  0
  2  3  1  0
 19 10  1  0
  4  5  1  0
 17 14  1  0
 10 11  1  6
 14 13  1  0
  8  9  1  1
 19 43  1  0
 19 44  1  0
 17 42  1  6
 13 37  1  0
 13 38  1  0
 12 35  1  0
 12 36  1  0
  4 26  1  1
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
 11 34  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
M  END

View in JSmol

Synonyms

Value	Source
1-(1,2,2-Trimethyl-3b-bromocyclopentane-1b-yl)-3a-chloro-4b-bromo-4-methylcyclohexane-1b-ol	Generator
1-(1,2,2-Trimethyl-3β-bromocyclopentane-1β-yl)-3α-chloro-4β-bromo-4-methylcyclohexane-1β-ol	Generator

Chemical Formula

C₁₅H₂₅Br₂ClO

Average Mass

416.6200 Da

Monoisotopic Mass

413.99607 Da

IUPAC Name

(1R,3S,4S)-4-bromo-1-[(1R,3S)-3-bromo-1,2,2-trimethylcyclopentyl]-3-chloro-4-methylcyclohexan-1-ol

Traditional Name

(1R,3S,4S)-4-bromo-1-[(1R,3S)-3-bromo-1,2,2-trimethylcyclopentyl]-3-chloro-4-methylcyclohexan-1-ol

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1(C([H])([H])C([H])([H])[C@@](Br)(C([H])([H])[H])[C@@]([H])(Cl)C1([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/C15H25Br2ClO/c1-12(2)10(16)5-6-14(12,4)15(19)8-7-13(3,17)11(18)9-15/h10-11,19H,5-9H2,1-4H3/t10-,11-,13-,14+,15+/m0/s1

InChI Key

RITYTGBWLLRFSG-XSXPHNMFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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 oculifera	JEOL database	Hegazy, M.-E. F., et al. J. Tetrahedron Lett. 55, 1711 (2014)

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
Cyclohexyl halide
Cyclohexanol
Cyclic alcohol
Tertiary alcohol
Alcohol
Organooxygen compound
Organochloride
Organobromide
Organohalogen compound
Hydrocarbon derivative
Organic oxygen compound
Alkyl halide
Alkyl chloride
Alkyl bromide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	5.19	ALOGPS
logP	4.79	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	87.99 m³·mol⁻¹	ChemAxon
Polarizability	36.63 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

32033860

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76900357

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hegazy, M.-E. F., et al. (2014). Hegazy, M.-E. F., et al. J. Tetrahedron Lett. 55, 1711 (2014). J. Tetrahedron Lett..

Showing NP-Card for oculiferane (NP0042891)

MOL for NP0042891 (oculiferane)

3D MOL for NP0042891 (oculiferane)

3D SDF for NP0042891 (oculiferane)

3D-SDF for NP0042891 (oculiferane)

PDB for NP0042891 (oculiferane)

3D PDB for NP0042891 (oculiferane)

SMILES for NP0042891 (oculiferane)

INCHI for NP0042891 (oculiferane)

Structure for NP0042891 (oculiferane)

3D Structure for NP0042891 (oculiferane)