NP-MRD: Showing NP-Card for 10-bromo-9-hydroxy-chamigra-2,7(14)-diene (NP0031452)

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Record Information

Version

2.0

Created at

2021-06-19 22:32:02 UTC

Updated at

2021-06-30 00:00:03 UTC

NP-MRD ID

NP0031452

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-bromo-9-hydroxy-chamigra-2,7(14)-diene

Provided By

JEOL Database JEOL Logo

Description

(2S,3R,6S)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]Undec-8-en-3-ol 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. 10-bromo-9-hydroxy-chamigra-2,7(14)-diene is found in Aplysia dactylomela, L. mariannensis, Laurencia majuscula and Laurencia rigida. 10-bromo-9-hydroxy-chamigra-2,7(14)-diene was first documented in 2001 (Vairappan, C. S., et al.). Based on a literature review very few articles have been published on (2S,3R,6S)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]Undec-8-en-3-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100323D          

 40 41  0  0  0  0            999 V2000
   -0.3664   -4.0121   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -2.6755   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.8048    0.4266 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1610   -0.8616    0.0964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3771   -1.6125    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -0.0915   -1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4053    1.1347   -1.5036 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9639   -2.4523 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1639   -0.0021   -3.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.8319   -2.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -1.9226   -2.0753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0725   -2.9020   -3.2652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4289   -3.5588   -3.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4211   -3.1548   -2.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417   -3.8644   -2.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.9612   -1.4932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0453   -1.0941   -1.8413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0887   -4.4616    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -4.7138   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -2.4248    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8686   -1.2244    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778   -0.1573    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -1.0018   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.6121   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407   -0.5248   -4.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501    0.5300   -3.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    0.7579   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -2.6237   -2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -2.3165   -3.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -1.2374   -3.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -3.6880   -3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -2.3765   -4.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -4.4134   -3.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7766   -4.7306   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518   -3.1868   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9311   -4.2210   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1998   -2.3049   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.3303   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2934   -0.5373   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.3404   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0  0  0  0
 16 14  1  0  0  0  0
  4  3  1  0  0  0  0
  6  8  1  0  0  0  0
  8 11  1  0  0  0  0
 11  2  1  1  0  0  0
  2  3  1  0  0  0  0
 14 13  2  0  0  0  0
  2  1  2  3  0  0  0
 13 12  1  0  0  0  0
 14 15  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
 11 17  1  0  0  0  0
  8  9  1  6  0  0  0
 11 12  1  0  0  0  0
  8 10  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 13 33  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  4 22  1  1  0  0  0
  6 24  1  1  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
  5 23  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
M  END

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.3664   -4.0121   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -2.6755   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.8048    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.8616    0.0964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3771   -1.6125    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -0.0915   -1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4053    1.1347   -1.5036 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9639   -2.4523 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1639   -0.0021   -3.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.8319   -2.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -1.9226   -2.0753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0725   -2.9020   -3.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4289   -3.5588   -3.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4211   -3.1548   -2.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417   -3.8644   -2.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.9612   -1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453   -1.0941   -1.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -4.4616    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -4.7138   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -2.4248    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8686   -1.2244    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778   -0.1573    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -1.0018   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.6121   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407   -0.5248   -4.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501    0.5300   -3.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    0.7579   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -2.6237   -2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -2.3165   -3.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -1.2374   -3.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -3.6880   -3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -2.3765   -4.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -4.4134   -3.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7766   -4.7306   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518   -3.1868   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9311   -4.2210   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1998   -2.3049   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.3303   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2934   -0.5373   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.3404   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
  4  3  1  0
  6  8  1  0
  8 11  1  0
 11  2  1  1
  2  3  1  0
 14 13  2  0
  2  1  2  3
 13 12  1  0
 14 15  1  0
  4  6  1  0
  4  5  1  0
  6  7  1  0
 11 17  1  0
  8  9  1  6
 11 12  1  0
  8 10  1  0
 17 39  1  0
 17 40  1  0
 16 37  1  0
 16 38  1  0
 13 33  1  0
 12 31  1  0
 12 32  1  0
  4 22  1  1
  6 24  1  1
  3 20  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
  5 23  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
M  END


  Mrv1652306202100323D          

 40 41  0  0  0  0            999 V2000
   -0.3664   -4.0121   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -2.6755   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.8048    0.4266 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1610   -0.8616    0.0964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3771   -1.6125    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -0.0915   -1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4053    1.1347   -1.5036 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9639   -2.4523 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1639   -0.0021   -3.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.8319   -2.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -1.9226   -2.0753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0725   -2.9020   -3.2652 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4289   -3.5588   -3.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4211   -3.1548   -2.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417   -3.8644   -2.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.9612   -1.4932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0453   -1.0941   -1.8413 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0887   -4.4616    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -4.7138   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -2.4248    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8686   -1.2244    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778   -0.1573    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -1.0018   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.6121   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407   -0.5248   -4.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501    0.5300   -3.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    0.7579   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -2.6237   -2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -2.3165   -3.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -1.2374   -3.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -3.6880   -3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -2.3765   -4.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -4.4134   -3.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7766   -4.7306   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518   -3.1868   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9311   -4.2210   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1998   -2.3049   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.3303   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2934   -0.5373   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.3404   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0  0  0  0
 16 14  1  0  0  0  0
  4  3  1  0  0  0  0
  6  8  1  0  0  0  0
  8 11  1  0  0  0  0
 11  2  1  1  0  0  0
  2  3  1  0  0  0  0
 14 13  2  0  0  0  0
  2  1  2  3  0  0  0
 13 12  1  0  0  0  0
 14 15  1  0  0  0  0
  4  6  1  0  0  0  0
  4  5  1  0  0  0  0
  6  7  1  0  0  0  0
 11 17  1  0  0  0  0
  8  9  1  6  0  0  0
 11 12  1  0  0  0  0
  8 10  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 13 33  1  0  0  0  0
 12 31  1  0  0  0  0
 12 32  1  0  0  0  0
  4 22  1  1  0  0  0
  6 24  1  1  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
  5 23  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
  9 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
 10 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031452

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H23BrO/c1-10-5-7-15(8-6-10)11(2)9-12(17)13(16)14(15,3)4/h5,12-13,17H,2,6-9H2,1,3-4H3/t12-,13-,15-/m1/s1

> <INCHI_KEY>
APALGGYWOOAWLG-UMVBOHGHSA-N

> <FORMULA>
C15H23BrO

> <MOLECULAR_WEIGHT>
299.252

> <EXACT_MASS>
298.093228

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
29.903063130310603

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3R,6S)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]undec-8-en-3-ol

> <ALOGPS_LOGP>
4.17

> <JCHEM_LOGP>
3.76670986

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.064318024758315

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2080672959707117

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
76.29039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,6S)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]undec-8-en-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
   -0.3664   -4.0121   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -2.6755   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.8048    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.8616    0.0964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3771   -1.6125    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -0.0915   -1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4053    1.1347   -1.5036 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9639   -2.4523 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1639   -0.0021   -3.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.8319   -2.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -1.9226   -2.0753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0725   -2.9020   -3.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4289   -3.5588   -3.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4211   -3.1548   -2.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417   -3.8644   -2.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.9612   -1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453   -1.0941   -1.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -4.4616    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -4.7138   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -2.4248    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8686   -1.2244    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778   -0.1573    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -1.0018   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.6121   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407   -0.5248   -4.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501    0.5300   -3.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    0.7579   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -2.6237   -2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -2.3165   -3.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -1.2374   -3.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -3.6880   -3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -2.3765   -4.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -4.4134   -3.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7766   -4.7306   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518   -3.1868   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9311   -4.2210   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1998   -2.3049   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.3303   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2934   -0.5373   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.3404   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
  4  3  1  0
  6  8  1  0
  8 11  1  0
 11  2  1  1
  2  3  1  0
 14 13  2  0
  2  1  2  3
 13 12  1  0
 14 15  1  0
  4  6  1  0
  4  5  1  0
  6  7  1  0
 11 17  1  0
  8  9  1  6
 11 12  1  0
  8 10  1  0
 17 39  1  0
 17 40  1  0
 16 37  1  0
 16 38  1  0
 13 33  1  0
 12 31  1  0
 12 32  1  0
  4 22  1  1
  6 24  1  1
  3 20  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
  5 23  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  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      -0.366  -4.012  -0.593  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.380  -2.676  -0.757  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.006  -1.805   0.427  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.161  -0.862   0.096  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.377  -1.613   0.040  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.881  -0.092  -1.201  0.00  0.00           C+0
HETATM    7 Br   UNK     0       2.405   1.135  -1.504  0.00  0.00          Br+0
HETATM    8  C   UNK     0       0.513  -0.964  -2.452  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.164  -0.002  -3.625  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.708  -1.832  -2.931  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.740  -1.923  -2.075  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.073  -2.902  -3.265  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.429  -3.559  -3.208  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.421  -3.155  -2.397  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.742  -3.864  -2.333  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.264  -1.961  -1.493  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.045  -1.094  -1.841  0.00  0.00           C+0
HETATM   18  H   UNK     0      -0.089  -4.462   0.357  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.624  -4.714  -1.377  0.00  0.00           H+0
HETATM   20  H   UNK     0       0.290  -2.425   1.287  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.869  -1.224   0.742  0.00  0.00           H+0
HETATM   22  H   UNK     0       1.278  -0.157   0.930  0.00  0.00           H+0
HETATM   23  H   UNK     0       3.075  -1.002  -0.260  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.063   0.612  -1.006  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.241  -0.525  -4.494  0.00  0.00           H+0
HETATM   26  H   UNK     0       1.050   0.530  -3.987  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.564   0.758  -3.323  0.00  0.00           H+0
HETATM   28  H   UNK     0       1.964  -2.624  -2.222  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.486  -2.317  -3.889  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.611  -1.237  -3.100  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.311  -3.688  -3.338  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.044  -2.377  -4.224  0.00  0.00           H+0
HETATM   33  H   UNK     0      -2.575  -4.413  -3.865  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.777  -4.731  -3.002  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.552  -3.187  -2.622  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.931  -4.221  -1.316  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.200  -2.305  -0.454  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.159  -1.330  -1.562  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.293  -0.537  -2.754  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.923  -0.340  -1.057  0.00  0.00           H+0
CONECT    1    2   18   19                                                  
CONECT    2   11    3    1                                                  
CONECT    3    4    2   20   21                                             
CONECT    4    3    6    5   22                                             
CONECT    5    4   23                                                       
CONECT    6    8    4    7   24                                             
CONECT    7    6                                                            
CONECT    8    6   11    9   10                                             
CONECT    9    8   25   26   27                                             
CONECT   10    8   28   29   30                                             
CONECT   11    8    2   17   12                                             
CONECT   12   13   11   31   32                                             
CONECT   13   14   12   33                                                  
CONECT   14   16   13   15                                                  
CONECT   15   14   34   35   36                                             
CONECT   16   17   14   37   38                                             
CONECT   17   16   11   39   40                                             
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    5                                                            
CONECT   24    6                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   10                                                            
CONECT   31   12                                                            
CONECT   32   12                                                            
CONECT   33   13                                                            
CONECT   34   15                                                            
CONECT   35   15                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   82    0
END

RDKit          3D

40 41  0  0  0  0  0  0  0  0999 V2000
   -0.3664   -4.0121   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3799   -2.6755   -0.7569 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0061   -1.8048    0.4266 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1610   -0.8616    0.0964 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3771   -1.6125    0.0395 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811   -0.0915   -1.2012 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4053    1.1347   -1.5036 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.5129   -0.9639   -2.4523 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1639   -0.0021   -3.6247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7084   -1.8319   -2.9312 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7402   -1.9226   -2.0753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0725   -2.9020   -3.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4289   -3.5588   -3.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4211   -3.1548   -2.3973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7417   -3.8644   -2.3335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2643   -1.9612   -1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453   -1.0941   -1.8413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887   -4.4616    0.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6235   -4.7138   -1.3769 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2903   -2.4248    1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8686   -1.2244    0.7419 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778   -0.1573    0.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0750   -1.0018   -0.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0629    0.6121   -1.0064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407   -0.5248   -4.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0501    0.5300   -3.9875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5641    0.7579   -3.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9636   -2.6237   -2.2223 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -2.3165   -3.8885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6109   -1.2374   -3.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3114   -3.6880   -3.3382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0435   -2.3765   -4.2241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5746   -4.4134   -3.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7766   -4.7306   -3.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5518   -3.1868   -2.6218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9311   -4.2210   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1998   -2.3049   -0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -1.3303   -1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2934   -0.5373   -2.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9230   -0.3404   -1.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 14  1  0
  4  3  1  0
  6  8  1  0
  8 11  1  0
 11  2  1  1
  2  3  1  0
 14 13  2  0
  2  1  2  3
 13 12  1  0
 14 15  1  0
  4  6  1  0
  4  5  1  0
  6  7  1  0
 11 17  1  0
  8  9  1  6
 11 12  1  0
  8 10  1  0
 17 39  1  0
 17 40  1  0
 16 37  1  0
 16 38  1  0
 13 33  1  0
 12 31  1  0
 12 32  1  0
  4 22  1  1
  6 24  1  1
  3 20  1  0
  3 21  1  0
  1 18  1  0
  1 19  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
  5 23  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₃BrO

Average Mass

299.2520 Da

Monoisotopic Mass

298.09323 Da

IUPAC Name

(2S,3R,6S)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]undec-8-en-3-ol

Traditional Name

(2S,3R,6S)-2-bromo-1,1,9-trimethyl-5-methylidenespiro[5.5]undec-8-en-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])=C(C([H])([H])[H])C([H])([H])C2([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]1([H])Br

InChI Identifier

InChI=1S/C15H23BrO/c1-10-5-7-15(8-6-10)11(2)9-12(17)13(16)14(15,3)4/h5,12-13,17H,2,6-9H2,1,3-4H3/t12-,13-,15-/m1/s1

InChI Key

APALGGYWOOAWLG-UMVBOHGHSA-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	Animalia	KNApSAcK
L. mariannensis	JEOL database	Vairappan, C. S., et al, Phytochemistry 58, 517 (2001)
Laurencia majuscula	LOTUS Database	35616633
Laurencia rigida	-	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
Secondary alcohol
Halohydrin
Bromohydrin
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen compound
Alkyl halide
Alkyl bromide
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	4.17	ALOGPS
logP	3.77	ChemAxon
logS	-4.6	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	76.29 m³·mol⁻¹	ChemAxon
Polarizability	29.9 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

552599

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

636905

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Vairappan, C. S., et al. (2001). Vairappan, C. S., et al, Phytochemistry 58, 517 (2001) . Phytochem..

Showing NP-Card for 10-bromo-9-hydroxy-chamigra-2,7(14)-diene (NP0031452)

MOL for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

3D MOL for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

3D SDF for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

3D-SDF for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

PDB for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

3D PDB for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

SMILES for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

INCHI for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

Structure for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )

3D Structure for NP0031452 (10-bromo-9-hydroxy-chamigra-2,7(14)-diene )