NP-MRD: Showing NP-Card for {5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate (NP0233302)

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Record Information

Version

1.0

Created at

2022-09-06 14:51:21 UTC

Updated at

2022-09-06 14:51:21 UTC

NP-MRD ID

NP0233302

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

Description

Ent-17-Acetoxy-16b-kauran-19-al belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. Ent-17-Acetoxy-16b-kauran-19-al is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, ent-17-acetoxy-16b-kauran-19-al has been detected, but not quantified in, fruits. {5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate is found in Annona glabra. It was first documented in 2000 (PMID: 11413487). This could make ent-17-acetoxy-16b-kauran-19-al a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061309182D          

 25 28  0  0  0  0            999 V2000
   -2.4912    0.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938    0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    1.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 15  1  1  0  0  0  0
 16  5  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18  7  1  0  0  0  0
 19  6  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21  3  1  0  0  0  0
 21  9  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 10  1  0  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 19  1  0  0  0  0
 23 14  2  0  0  0  0
 24 15  2  0  0  0  0
 25 13  1  0  0  0  0
 25 15  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    7.0016    0.2375    1.2496 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6088   -0.0794    0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8348   -0.5877    1.5801 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2136    0.1716   -0.4902 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0177   -0.0229   -1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8295    0.6792   -0.7019 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6475    0.3280   -1.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4338    0.5446   -0.7772 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5083    1.4375   -1.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349    1.5849   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4663    0.2712   -0.7645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6476    0.3733    0.1966 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.1914    1.7933    0.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7424   -0.5421   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5413   -0.9002    0.6613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1602    0.1172    1.5897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8173   -1.3523    1.6509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2691   -1.9092    0.4067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6180   -0.9426   -0.5627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7166   -1.7057   -1.9169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1795   -0.7461   -0.3333 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2929   -0.9717    1.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883   -0.7299    1.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    0.5670    0.6567 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9557    1.3699    0.3708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9768    1.1627    1.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3122   -0.6131    1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6954    0.3083    0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8966   -1.1338   -1.2718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181    0.2947   -2.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9777    1.7859   -0.8912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6357    0.9696   -2.5115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7558   -0.7300   -1.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086    2.4375   -1.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7186    1.1228   -2.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    2.3659   -1.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4167    1.8368    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9753    0.3054   -1.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6133    2.5170    0.6556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3708    2.0672   -0.9714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2163    1.7559    0.5544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8146   -0.8869   -1.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3534    0.7765    1.8920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0267    0.3567    2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8015   -1.8543    1.9141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2233   -1.5101    2.5794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1267   -2.4158   -0.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5656   -2.7629    0.5959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889   -1.7625   -2.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3531   -2.7387   -1.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0954   -1.2417   -2.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3977   -1.5640   -0.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1903   -2.0738    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2664   -0.3862    1.8447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0205   -0.7478    2.2734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3565   -1.6134    0.7885 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7749    1.1885    1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3354    1.4295    1.2498 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2385    2.3683   -0.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  8  7  1  6
  8 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 19  1  0
 19 20  1  6
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 12  1  0
 12 13  1  0
 12 14  1  6
 14 15  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
 24  6  1  0
 11 19  1  0
 21  8  1  0
  9  8  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  6
  7 32  1  0
  7 33  1  0
 25 58  1  0
 25 59  1  0
 24 57  1  1
 23 55  1  0
 23 56  1  0
 22 53  1  0
 22 54  1  0
 21 52  1  6
 20 49  1  0
 20 50  1  0
 20 51  1  0
 18 47  1  0
 18 48  1  0
 17 45  1  0
 17 46  1  0
 16 43  1  0
 16 44  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 14 42  1  0
 11 38  1  6
 10 36  1  0
 10 37  1  0
  9 34  1  0
  9 35  1  0
M  END


  Mrv0541 05061309182D          

 25 28  0  0  0  0            999 V2000
   -2.4912    0.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7827    2.9325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7366    0.4428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550    0.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1623    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942    0.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314    2.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6222    1.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5455    0.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    2.4782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0998    1.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7382    2.0342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6778    1.4980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862    2.5891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9938    0.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599    0.6390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1409    1.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    2.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1835    1.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    2.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0032    1.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5715    1.6963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    3.4139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3150    1.7016    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1751    0.8399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  4  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 15  1  1  0  0  0  0
 16  5  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  1  0  0  0  0
 18  7  1  0  0  0  0
 19  6  1  0  0  0  0
 20  2  1  0  0  0  0
 20  8  1  0  0  0  0
 20 14  1  0  0  0  0
 20 18  1  0  0  0  0
 21  3  1  0  0  0  0
 21  9  1  0  0  0  0
 21 18  1  0  0  0  0
 21 19  1  0  0  0  0
 22 10  1  0  0  0  0
 22 11  1  0  0  0  0
 22 12  1  0  0  0  0
 22 19  1  0  0  0  0
 23 14  2  0  0  0  0
 24 15  2  0  0  0  0
 25 13  1  0  0  0  0
 25 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0233302

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O3/c1-15(24)25-13-17-12-22-10-7-18-20(2,14-23)8-4-9-21(18,3)19(22)6-5-16(17)11-22/h14,16-19H,4-13H2,1-3H3

> <INCHI_KEY>
AXCCTUATUTWPBD-UHFFFAOYSA-N

> <FORMULA>
C22H34O3

> <MOLECULAR_WEIGHT>
346.5036

> <EXACT_MASS>
346.250794954

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.416074530040376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
4.079260846666667

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.741728233266126

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
97.66389999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.650   0.529   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.061   5.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.108   0.826   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.129   1.420   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.170   0.028   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.722   0.398   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.099   4.917   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.628   2.877   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.618   1.124   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.569   4.626   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.053   2.140   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.378   3.797   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.265   2.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.934   4.833   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.722   1.758   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.045   1.193   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.263   2.606   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.105   3.741   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.076   1.981   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.616   4.037   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.606   2.284   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.933   3.166   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.904   6.373   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.321   3.176   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -2.194   1.568   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    8    9                                                       
CONECT    5    6   16                                                       
CONECT    6    5   19                                                       
CONECT    7   10   18                                                       
CONECT    8    4   20                                                       
CONECT    9    4   21                                                       
CONECT   10    7   22                                                       
CONECT   11   16   22                                                       
CONECT   12   17   22                                                       
CONECT   13   17   25                                                       
CONECT   14   20   23                                                       
CONECT   15    1   24   25                                                  
CONECT   16    5   11   17                                                  
CONECT   17   12   13   16                                                  
CONECT   18    7   20   21                                                  
CONECT   19    6   21   22                                                  
CONECT   20    2    8   14   18                                             
CONECT   21    3    9   18   19                                             
CONECT   22   10   11   12   19                                             
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

View in JSmol

Synonyms

Value	Source
{5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetic acid	Generator

Chemical Formula

C₂₂H₃₄O₃

Average Mass

346.5036 Da

Monoisotopic Mass

346.25079 Da

IUPAC Name

{5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

Traditional Name

{5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1CC23CC1CCC2C1(C)CCCC(C)(C=O)C1CC3

InChI Identifier

InChI=1S/C22H34O3/c1-15(24)25-13-17-12-22-10-7-18-20(2,14-23)8-4-9-21(18,3)19(22)6-5-16(17)11-22/h14,16-19H,4-13H2,1-3H3

InChI Key

AXCCTUATUTWPBD-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
Annona glabra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Kaurane diterpenoids

Alternative Parents

Not Available

Substituents

Not Available

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	3.96	ALOGPS
logP	4.08	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.66 m³·mol⁻¹	ChemAxon
Polarizability	40.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036722

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015659

KNApSAcK ID

Not Available

Chemspider ID

467185

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

536366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
LOTUS database [Link]

Showing NP-Card for {5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate (NP0233302)

MOL for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D MOL for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D SDF for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D-SDF for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

PDB for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D PDB for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

SMILES for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

INCHI for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

Structure for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)

3D Structure for NP0233302 ({5-formyl-5,9-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-14-yl}methyl acetate)