NP-MRD: Showing NP-Card for 5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate (NP0219083)

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Record Information

Version

2.0

Created at

2022-09-05 19:57:48 UTC

Updated at

2022-09-05 19:57:48 UTC

NP-MRD ID

NP0219083

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate

Description

5,6,11-Trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]Hexadec-8-en-14-yl hexadeca-2,4,6-trienoate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate is found in Hippomane mancinella. 5,6,11-Trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]Hexadec-8-en-14-yl hexadeca-2,4,6-trienoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121514142D          

 44 48  0  0  0  0            999 V2000
  -11.0282   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3137   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5993   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8848   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1703   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4559   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7414   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0269   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3124   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5980   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8835   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1690   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7401   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4033   -6.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111   -5.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4033   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -5.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6408   -5.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -6.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -5.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6408   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9422   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1258   -2.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7306   -2.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450   -2.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9436   -1.5189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4122   -3.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267   -2.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4739   -4.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -3.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691   -4.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159   -5.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0350   -5.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961   -6.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944   -4.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9430   -4.2743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -3.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8310   -4.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 14 13  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 33 39  1  0  0  0  0
 39 40  2  0  0  0  0
 25 41  1  0  0  0  0
 19 41  1  0  0  0  0
 41 42  1  0  0  0  0
 19 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END

     RDKit          3D

 96100  0  0  0  0  0  0  0  0999 V2000
   10.6403    0.5868    3.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6559    0.5167    2.0385 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0485   -0.1180    0.8306 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5589   -1.5327    1.0715 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9721   -2.1110   -0.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7952   -1.3635   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6533   -1.3410    0.3021 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4682   -0.5914   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3331   -0.5902    0.7235 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1442    0.1057    0.1940 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9597   -0.4088    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032   -1.8193    0.2914 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5004   -2.3575    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3122   -3.1453    0.0225 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5023    0.4821   -1.4811 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2511    1.3377   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5293    1.4868    0.5002 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1057    1.4606    1.9679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5192    0.3457    0.3285 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8712   -0.7634    0.9160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6967    0.6328    1.1533 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.4402   -0.4931    1.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5399    0.0199    2.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6229   -0.7287    3.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5632    1.4739    2.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1105    2.3629    2.7240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7264    1.5968    0.7902 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3152    2.9179    0.6989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7313    1.2294   -0.2776 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2767   -0.0218    0.0470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9105    1.0212   -1.5406 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0174    2.1931   -2.4302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1088    2.2645   -3.4784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0575   -0.0929   -2.3476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2011   -0.1109   -1.3368 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.9139   -0.3039   -3.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0061    1.5283    1.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2002    0.2382   -0.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
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 28 80  1  0
 28 81  1  0
 32 82  1  0
 33 83  1  6
 34 84  1  0
 36 85  1  0
 36 86  1  0
 37 87  1  0
 39 88  1  1
 40 89  1  1
 41 90  1  1
 43 91  1  0
 43 92  1  0
 43 93  1  0
 44 94  1  0
 44 95  1  0
 44 96  1  0
M  END


  Mrv0541 04121514142D          

 44 48  0  0  0  0            999 V2000
  -11.0282   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3137   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5993   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8848   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1703   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4559   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7414   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0269   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3124   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5980   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8835   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1690   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4546   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7401   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0256   -6.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111   -5.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4033   -6.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3111   -5.0700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4033   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -5.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6408   -5.3720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -6.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533   -4.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -5.4008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6408   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9422   -3.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1258   -2.3707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7306   -2.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2450   -2.2869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9436   -1.5189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4122   -3.3966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1267   -2.9841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4739   -4.2193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -3.7752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691   -4.7805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2159   -5.5290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0350   -5.4305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5961   -6.0353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1944   -4.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9430   -4.2743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8158   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0092   -3.9430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3578   -3.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8310   -4.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  4  0  0  0
 10 11  2  0  0  0  0
 12 11  1  4  0  0  0
 12 13  2  0  0  0  0
 14 13  1  4  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 33 39  1  0  0  0  0
 39 40  2  0  0  0  0
 25 41  1  0  0  0  0
 19 41  1  0  0  0  0
 41 42  1  0  0  0  0
 19 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219083

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCC=CC=CC=CC(=O)OC12CC(C)C3(O)C4C=C(C)C(=O)C4(O)C(O)C4(CO)OC4C3C1C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C36H52O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(38)43-34-21-24(3)35(41)25-20-23(2)29(39)36(25,42)31(40)33(22-37)30(44-33)27(35)28(34)32(34,4)5/h14-20,24-25,27-28,30-31,37,40-42H,6-13,21-22H2,1-5H3

> <INCHI_KEY>
NEZVVESVXBEHTR-UHFFFAOYSA-N

> <FORMULA>
C36H52O8

> <MOLECULAR_WEIGHT>
612.804

> <EXACT_MASS>
612.366218634

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
70.34207286162967

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
5.292379269333334

> <ALOGPS_LOGS>
-5.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.243593796947774

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.644878485546364

> <JCHEM_PKA_STRONGEST_BASIC>
-3.149657119662537

> <JCHEM_POLAR_SURFACE_AREA>
136.82000000000002

> <JCHEM_REFRACTIVITY>
170.91680000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0     -20.586 -11.774   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -19.252 -11.004   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -17.919 -11.774   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.585 -11.004   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -15.251 -11.774   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -13.918 -11.004   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -12.584 -11.774   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.250 -11.004   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.917 -11.774   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.583 -11.004   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.249 -11.774   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.916 -11.004   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.582 -11.774   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.248 -11.004   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.914 -11.774   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.581 -11.004   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.753 -11.774   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -0.581  -9.464   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.753  -8.694   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.523 -10.028   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.063 -10.028   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.833 -11.361   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.833  -8.694   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.501 -10.081   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.063  -7.360   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.625  -5.927   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.968  -4.425   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.097  -5.473   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       6.057  -4.269   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.495  -2.835   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.369  -6.340   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       7.703  -5.570   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.485  -7.876   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.782  -7.047   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.356  -8.924   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.003 -10.321   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.532 -10.137   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.579 -11.266   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.830  -8.626   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.227  -7.979   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.523  -7.360   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -0.017  -7.360   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -0.668  -5.965   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      -1.551  -7.495   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   41   42                                             
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   35                                             
CONECT   24   23                                                            
CONECT   25   23   26   41                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   28                                                       
CONECT   28   27   26   29   31                                             
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35   39                                             
CONECT   34   33                                                            
CONECT   35   33   23   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   33   40                                                  
CONECT   40   39                                                            
CONECT   41   25   19   42                                                  
CONECT   42   41   19   43   44                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
5,6,11-Trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0,.0,.0,]hexadec-8-en-14-yl hexadeca-2,4,6-trienoic acid	Generator
5,6,11-Trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoic acid	Generator

Chemical Formula

C₃₆H₅₂O₈

Average Mass

612.8040 Da

Monoisotopic Mass

612.36622 Da

IUPAC Name

5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate

Traditional Name

5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCC=CC=CC=CC(=O)OC12CC(C)C3(O)C4C=C(C)C(=O)C4(O)C(O)C4(CO)OC4C3C1C2(C)C

InChI Identifier

InChI=1S/C36H52O8/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-26(38)43-34-21-24(3)35(41)25-20-23(2)29(39)36(25,42)31(40)33(22-37)30(44-33)27(35)28(34)32(34,4)5/h14-20,24-25,27-28,30-31,37,40-42H,6-13,21-22H2,1-5H3

InChI Key

NEZVVESVXBEHTR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Hippomane mancinella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Carane monoterpenoid
Fatty acid ester
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Ketone
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Polyol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Alcohol
Organooxygen compound
Carbonyl group
Primary alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	5.45	ALOGPS
logP	5.29	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	11.64	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.82 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	170.92 m³·mol⁻¹	ChemAxon
Polarizability	70.34 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5088572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate (NP0219083)

MOL for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

3D MOL for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

3D SDF for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

3D-SDF for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

PDB for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

3D PDB for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

SMILES for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

INCHI for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

Structure for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)

3D Structure for NP0219083 (5,6,11-trihydroxy-4-(hydroxymethyl)-8,12,15,15-tetramethyl-7-oxo-3-oxapentacyclo[9.5.0.0²,⁴.0⁶,¹⁰.0¹⁴,¹⁶]hexadec-8-en-14-yl hexadeca-2,4,6-trienoate)