NP-MRD: Showing NP-Card for isoobtusol (NP0029201)

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Record Information

Version

2.0

Created at

2021-06-19 20:53:30 UTC

Updated at

2021-06-29 23:56:25 UTC

NP-MRD ID

NP0029201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

isoobtusol

Provided By

JEOL Database JEOL Logo

Description

isoobtusol is found in Aplysia dactylomela, Laurencia dendroidea, Laurencia majuscula and Laurencia obtusa . isoobtusol was first documented in 2012 (PMID: 23170082). Based on a literature review very few articles have been published on Isoobtusol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192122533D          

 42 43  0  0  0  0            999 V2000
    2.8783   -2.3146   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.2909   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3323   -1.1823    0.9770 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7858    0.0826    1.7020 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1472    0.1835    2.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.3506    0.8528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3008    1.9161    0.9251 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1744    1.2386   -0.6039 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7322    1.2783   -0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    2.5304   -1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -0.1364   -1.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5513   -0.2695   -2.7091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0893   -1.3557   -3.6939 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5970   -1.3130   -4.0255 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2137   -2.4823   -4.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    0.3238   -5.1343 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688   -1.2139   -2.7571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4258   -2.7958   -1.9123 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2199   -0.1324   -1.7699 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0320   -3.0661    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712   -2.4549   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.2086    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -2.0471    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -0.0209    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2202    0.4408    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0685    2.1888    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    1.3892   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1296    0.3812    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387    2.1366    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    2.5842   -2.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    2.6378   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    3.4201   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6819   -3.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142   -0.4431   -2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3331   -2.3446   -3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -1.2619   -4.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.4364   -5.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -2.4746   -5.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4539   -3.4515   -4.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997   -0.9662   -3.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190    0.8292   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.1874   -0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  2  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 17  1  0  0  0  0
 17 19  1  0  0  0  0
  2  3  1  0  0  0  0
 11  8  1  0  0  0  0
  8  6  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  1  0  0  0  0
 14 15  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
  4  5  1  0  0  0  0
 14 16  1  6  0  0  0
  8  9  1  1  0  0  0
 11 19  1  0  0  0  0
  8 10  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  2  3  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 17 40  1  6  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
  6 26  1  1  0  0  0
  4 24  1  1  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 25  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    2.8783   -2.3146   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.2909   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3323   -1.1823    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.0826    1.7020 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1472    0.1835    2.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.3506    0.8528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3008    1.9161    0.9251 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1744    1.2386   -0.6039 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7322    1.2783   -0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    2.5304   -1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -0.1364   -1.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5513   -0.2695   -2.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -1.3557   -3.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5970   -1.3130   -4.0255 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2137   -2.4823   -4.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    0.3238   -5.1343 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688   -1.2139   -2.7571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4258   -2.7958   -1.9123 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2199   -0.1324   -1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -3.0661    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712   -2.4549   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.2086    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -2.0471    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -0.0209    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2202    0.4408    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0685    2.1888    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    1.3892   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1296    0.3812    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387    2.1366    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    2.5842   -2.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    2.6378   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    3.4201   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6819   -3.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142   -0.4431   -2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3331   -2.3446   -3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -1.2619   -4.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.4364   -5.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -2.4746   -5.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4539   -3.4515   -4.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997   -0.9662   -3.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190    0.8292   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.1874   -0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  2  1  1
 12 13  1  0
 13 14  1  0
 14 17  1  0
 17 19  1  0
  2  3  1  0
 11  8  1  0
  8  6  1  0
  6  4  1  0
  4  3  1  0
 14 15  1  0
  6  7  1  0
 11 12  1  0
  4  5  1  0
 14 16  1  6
  8  9  1  1
 11 19  1  0
  8 10  1  0
 17 18  1  0
  2  1  2  3
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 17 40  1  6
 19 41  1  0
 19 42  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
  6 26  1  1
  4 24  1  1
  3 22  1  0
  3 23  1  0
  5 25  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
  1 20  1  0
  1 21  1  0
M  END


  Mrv1652306192122533D          

 42 43  0  0  0  0            999 V2000
    2.8783   -2.3146   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.2909   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3323   -1.1823    0.9770 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7858    0.0826    1.7020 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1472    0.1835    2.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.3506    0.8528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3008    1.9161    0.9251 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1744    1.2386   -0.6039 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7322    1.2783   -0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    2.5304   -1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -0.1364   -1.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5513   -0.2695   -2.7091 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0893   -1.3557   -3.6939 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5970   -1.3130   -4.0255 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2137   -2.4823   -4.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    0.3238   -5.1343 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688   -1.2139   -2.7571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4258   -2.7958   -1.9123 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2199   -0.1324   -1.7699 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0320   -3.0661    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712   -2.4549   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.2086    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -2.0471    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -0.0209    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2202    0.4408    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0685    2.1888    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    1.3892   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1296    0.3812    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387    2.1366    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    2.5842   -2.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    2.6378   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    3.4201   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6819   -3.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142   -0.4431   -2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3331   -2.3446   -3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -1.2619   -4.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.4364   -5.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -2.4746   -5.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4539   -3.4515   -4.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997   -0.9662   -3.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190    0.8292   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.1874   -0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  2  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 17  1  0  0  0  0
 17 19  1  0  0  0  0
  2  3  1  0  0  0  0
 11  8  1  0  0  0  0
  8  6  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  1  0  0  0  0
 14 15  1  0  0  0  0
  6  7  1  0  0  0  0
 11 12  1  0  0  0  0
  4  5  1  0  0  0  0
 14 16  1  6  0  0  0
  8  9  1  1  0  0  0
 11 19  1  0  0  0  0
  8 10  1  0  0  0  0
 17 18  1  0  0  0  0
  2  1  2  3  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 13 35  1  0  0  0  0
 13 36  1  0  0  0  0
 17 40  1  6  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 15 37  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
  6 26  1  1  0  0  0
  4 24  1  1  0  0  0
  3 22  1  0  0  0  0
  3 23  1  0  0  0  0
  5 25  1  0  0  0  0
  9 27  1  0  0  0  0
  9 28  1  0  0  0  0
  9 29  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  1 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C([H])([H])C(=C([H])[H])[C@]2(C([H])([H])C([H])([H])[C@@](Br)(C([H])([H])[H])[C@@]([H])(Cl)C2([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])Br

> <INCHI_IDENTIFIER>
InChI=1S/C15H23Br2ClO/c1-9-7-10(19)12(16)13(2,3)15(9)6-5-14(4,17)11(18)8-15/h10-12,19H,1,5-8H2,2-4H3/t10-,11-,12-,14-,15+/m0/s1

> <INCHI_KEY>
JPQFUHCOKXIWBB-ZCRGAIPPSA-N

> <FORMULA>
C15H23Br2ClO

> <MOLECULAR_WEIGHT>
414.61

> <EXACT_MASS>
411.980419

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
35.03686953142856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-ol

> <ALOGPS_LOGP>
5.44

> <JCHEM_LOGP>
4.598903753999999

> <ALOGPS_LOGS>
-6.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.064348045473913

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2080541649097096

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
87.64649999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.63e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
    2.8783   -2.3146   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.2909   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3323   -1.1823    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.0826    1.7020 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1472    0.1835    2.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.3506    0.8528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3008    1.9161    0.9251 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1744    1.2386   -0.6039 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7322    1.2783   -0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    2.5304   -1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -0.1364   -1.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5513   -0.2695   -2.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -1.3557   -3.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5970   -1.3130   -4.0255 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2137   -2.4823   -4.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    0.3238   -5.1343 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688   -1.2139   -2.7571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4258   -2.7958   -1.9123 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2199   -0.1324   -1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -3.0661    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712   -2.4549   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.2086    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -2.0471    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -0.0209    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2202    0.4408    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0685    2.1888    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    1.3892   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1296    0.3812    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387    2.1366    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    2.5842   -2.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    2.6378   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    3.4201   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6819   -3.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142   -0.4431   -2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3331   -2.3446   -3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -1.2619   -4.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.4364   -5.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -2.4746   -5.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4539   -3.4515   -4.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997   -0.9662   -3.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190    0.8292   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.1874   -0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  2  1  1
 12 13  1  0
 13 14  1  0
 14 17  1  0
 17 19  1  0
  2  3  1  0
 11  8  1  0
  8  6  1  0
  6  4  1  0
  4  3  1  0
 14 15  1  0
  6  7  1  0
 11 12  1  0
  4  5  1  0
 14 16  1  6
  8  9  1  1
 11 19  1  0
  8 10  1  0
 17 18  1  0
  2  1  2  3
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 17 40  1  6
 19 41  1  0
 19 42  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
  6 26  1  1
  4 24  1  1
  3 22  1  0
  3 23  1  0
  5 25  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
  1 20  1  0
  1 21  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       2.878  -2.315  -0.555  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.023  -1.291  -0.371  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.332  -1.182   0.977  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.786   0.083   1.702  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.147   0.184   2.977  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.594   1.351   0.853  0.00  0.00           C+0
HETATM    7 Br   UNK     0      -0.301   1.916   0.925  0.00  0.00          Br+0
HETATM    8  C   UNK     0       2.174   1.239  -0.604  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.732   1.278  -0.438  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.847   2.530  -1.404  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.739  -0.136  -1.371  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.551  -0.270  -2.709  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.089  -1.356  -3.694  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.597  -1.313  -4.026  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.214  -2.482  -4.947  0.00  0.00           C+0
HETATM   16 Br   UNK     0       0.254   0.324  -5.134  0.00  0.00          Br+0
HETATM   17  C   UNK     0      -0.269  -1.214  -2.757  0.00  0.00           C+0
HETATM   18 Cl   UNK     0      -0.426  -2.796  -1.912  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       0.220  -0.132  -1.770  0.00  0.00           C+0
HETATM   20  H   UNK     0       3.032  -3.066   0.216  0.00  0.00           H+0
HETATM   21  H   UNK     0       3.471  -2.455  -1.450  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.243  -1.209   0.869  0.00  0.00           H+0
HETATM   23  H   UNK     0       1.557  -2.047   1.616  0.00  0.00           H+0
HETATM   24  H   UNK     0       2.854  -0.021   1.926  0.00  0.00           H+0
HETATM   25  H   UNK     0       0.220   0.441   2.816  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.068   2.189   1.380  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.242   1.389  -1.401  0.00  0.00           H+0
HETATM   28  H   UNK     0       4.130   0.381   0.044  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.039   2.137   0.172  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.401   2.584  -2.346  0.00  0.00           H+0
HETATM   31  H   UNK     0       0.789   2.638  -1.647  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.132   3.420  -0.828  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.521   0.682  -3.249  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.614  -0.443  -2.503  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.333  -2.345  -3.293  0.00  0.00           H+0
HETATM   36  H   UNK     0       2.687  -1.262  -4.611  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.754  -2.436  -5.900  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.858  -2.475  -5.177  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.454  -3.451  -4.498  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.300  -0.966  -3.038  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.019   0.829  -2.233  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.424  -0.187  -0.890  0.00  0.00           H+0
CONECT    1    2   20   21                                                  
CONECT    2   11    3    1                                                  
CONECT    3    2    4   22   23                                             
CONECT    4    6    3    5   24                                             
CONECT    5    4   25                                                       
CONECT    6    8    4    7   26                                             
CONECT    7    6                                                            
CONECT    8   11    6    9   10                                             
CONECT    9    8   27   28   29                                             
CONECT   10    8   30   31   32                                             
CONECT   11    2    8   12   19                                             
CONECT   12   13   11   33   34                                             
CONECT   13   12   14   35   36                                             
CONECT   14   13   17   15   16                                             
CONECT   15   14   37   38   39                                             
CONECT   16   14                                                            
CONECT   17   14   19   18   40                                             
CONECT   18   17                                                            
CONECT   19   17   11   41   42                                             
CONECT   20    1                                                            
CONECT   21    1                                                            
CONECT   22    3                                                            
CONECT   23    3                                                            
CONECT   24    4                                                            
CONECT   25    5                                                            
CONECT   26    6                                                            
CONECT   27    9                                                            
CONECT   28    9                                                            
CONECT   29    9                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   13                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   17                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   86    0
END

RDKit          3D

42 43  0  0  0  0  0  0  0  0999 V2000
    2.8783   -2.3146   -0.5551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0235   -1.2909   -0.3709 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3323   -1.1823    0.9770 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.0826    1.7020 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1472    0.1835    2.9767 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5941    1.3506    0.8528 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3008    1.9161    0.9251 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.1744    1.2386   -0.6039 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7322    1.2783   -0.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8471    2.5304   -1.4039 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7390   -0.1364   -1.3714 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5513   -0.2695   -2.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0893   -1.3557   -3.6939 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5970   -1.3130   -4.0255 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2137   -2.4823   -4.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2544    0.3238   -5.1343 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.2688   -1.2139   -2.7571 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4258   -2.7958   -1.9123 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.2199   -0.1324   -1.7699 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0320   -3.0661    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4712   -2.4549   -1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2432   -1.2086    0.8694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5571   -2.0471    1.6156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8543   -0.0209    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2202    0.4408    2.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0685    2.1888    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417    1.3892   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1296    0.3812    0.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0387    2.1366    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4012    2.5842   -2.3458 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    2.6378   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1318    3.4201   -0.8281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5211    0.6819   -3.2486 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6142   -0.4431   -2.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3331   -2.3446   -3.2925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867   -1.2619   -4.6109 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7543   -2.4364   -5.9004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582   -2.4746   -5.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4539   -3.4515   -4.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2997   -0.9662   -3.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0190    0.8292   -2.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4243   -0.1874   -0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  2  1  1
 12 13  1  0
 13 14  1  0
 14 17  1  0
 17 19  1  0
  2  3  1  0
 11  8  1  0
  8  6  1  0
  6  4  1  0
  4  3  1  0
 14 15  1  0
  6  7  1  0
 11 12  1  0
  4  5  1  0
 14 16  1  6
  8  9  1  1
 11 19  1  0
  8 10  1  0
 17 18  1  0
  2  1  2  3
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 17 40  1  6
 19 41  1  0
 19 42  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
  6 26  1  1
  4 24  1  1
  3 22  1  0
  3 23  1  0
  5 25  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
  1 20  1  0
  1 21  1  0
M  END

View in JSmol

Synonyms

Value	Source
Iso-obtusol	MeSH

Chemical Formula

C₁₅H₂₃Br₂ClO

Average Mass

414.6100 Da

Monoisotopic Mass

411.98042 Da

IUPAC Name

(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-ol

Traditional Name

(2R,3S,6R,8S,9S)-2,9-dibromo-8-chloro-1,1,9-trimethyl-5-methylidenespiro[5.5]undecan-3-ol

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C(=C([H])[H])[C@]2(C([H])([H])C([H])([H])[C@@](Br)(C([H])([H])[H])[C@@]([H])(Cl)C2([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@@]1([H])Br

InChI Identifier

InChI=1S/C15H23Br2ClO/c1-9-7-10(19)12(16)13(2,3)15(9)6-5-14(4,17)11(18)8-15/h10-12,19H,1,5-8H2,2-4H3/t10-,11-,12-,14-,15+/m0/s1

InChI Key

JPQFUHCOKXIWBB-ZCRGAIPPSA-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 dactylomela	JEOL database	Wessels, M., et al, J. Nat. Prod. 63, 920 (2000)
Laurencia dendroidea	LOTUS Database	35616633
Laurencia majuscula	-	KNApSAcK
Laurencia obtusa	-	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chamigranes. These are sesquiterpenoids characterized by a 1,1,5,9-tetramethylspiro[5,5]undecane skeleton, formally obtained by linking the C1-C6 and C6-C11 of farnesane together. They are predominantly isolated from algae.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Chamigranes

Alternative Parents

Substituents

Chamigrane sesquiterpenoid
Cyclic alcohol
Bromohydrin
Secondary alcohol
Halohydrin
Alcohol
Organobromide
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Alkyl halide
Alkyl chloride
Alkyl bromide
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.44	ALOGPS
logP	4.6	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	14.06	ChemAxon
pKa (Strongest Basic)	-3.2	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	0	ChemAxon
Refractivity	87.65 m³·mol⁻¹	ChemAxon
Polarizability	35.04 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

10191589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14108771

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lang KL, Silva IT, Zimmermann LA, Lhullier C, Manalich Arana MV, Palermo JA, Falkenberg M, Simoes CM, Schenkel EP, Duran FJ: Cytotoxic activity of semi-synthetic derivatives of elatol and isoobtusol. Mar Drugs. 2012 Oct;10(10):2254-64. doi: 10.3390/md10102254. Epub 2012 Oct 18. [PubMed:23170082 ]
Wessels, M., et al. (2000). Wessels, M., et al, J. Nat. Prod. 63, 920 (2000). J. Nat. Prod..

Showing NP-Card for isoobtusol (NP0029201)

MOL for NP0029201 (isoobtusol)

3D MOL for NP0029201 (isoobtusol)

3D SDF for NP0029201 (isoobtusol)

3D-SDF for NP0029201 (isoobtusol)

PDB for NP0029201 (isoobtusol)

3D PDB for NP0029201 (isoobtusol)

SMILES for NP0029201 (isoobtusol)

INCHI for NP0029201 (isoobtusol)

Structure for NP0029201 (isoobtusol)

3D Structure for NP0029201 (isoobtusol)