NP-MRD: Showing NP-Card for (1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate (NP0248627)

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Record Information

Version

2.0

Created at

2022-09-07 10:56:50 UTC

Updated at

2022-09-07 10:56:50 UTC

NP-MRD ID

NP0248627

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate

Description

Hypoestoxide belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group). (1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate was first documented in 2003 (PMID: 12962514). Based on a literature review a significant number of articles have been published on hypoestoxide (PMID: 26683203) (PMID: 24315792) (PMID: 18979485) (PMID: 17729410) (PMID: 17568581).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072212572D          

 27 30  0  0  1  0            999 V2000
    2.6012   -2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296   -1.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879   -1.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -1.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -0.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9862   -0.0100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1145    0.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8845    1.1013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6544    1.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261    0.5827    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0447    1.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2960    0.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8093   -0.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6810   -1.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -0.7509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3357   -1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9110   -1.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1411   -1.8622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0128   -2.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6544   -3.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261   -4.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4243   -2.8994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -1.3436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6278   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1685    0.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24  2  1  6  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
   -2.1241    0.3134   -1.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -0.5195   -1.1012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6624   -1.9754   -1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6521   -2.4311   -1.9684 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6132   -2.9257   -0.9087 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0102   -2.4860    0.3850 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4600   -2.1938    0.3426 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0623   -1.8399   -0.9644 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3272   -2.2653   -1.3506 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3635   -1.0728   -0.6856 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9723   -1.1685    0.6961 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3900    0.2419   -1.3903 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8921    1.3879   -0.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9080    2.2395   -1.1932 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8692    1.4843   -1.7471 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5880    2.4550   -0.8063 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1219    3.6447   -1.4947 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0819    2.1563    0.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9823    1.1359    0.7186 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2820    1.4474    0.5002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3550    1.5047    1.3367 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7341    1.8692    0.9219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0351    1.2120    2.4987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6937   -0.1869    0.0585 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8315   -1.3618    1.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3367   -1.0497    2.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2486   -1.8613    1.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    0.0138   -2.7566 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0286    1.3706   -1.7521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822   -3.9280   -0.8406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2076   -3.0326   -1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1332   -3.3432    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7008   -1.3576    1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698   -3.0543    0.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827   -1.4512   -1.8217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8819   -2.1824    1.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0749   -0.9610    0.6178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5772   -0.4658    1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7511    0.1562   -2.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4250    0.5045   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7585    1.9776   -0.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4662    0.8861    0.3937 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3892    2.8929   -1.9818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7435    3.3056   -2.3354 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6372    4.3425   -1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6690    4.1970   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2966    3.1224    1.0033 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9599    1.9505    1.1989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9215    0.8884    1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7579    2.4998    0.0252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3043    0.9373    0.7047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2134    2.3404    1.8080 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933   -0.1601   -0.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2081   -0.7511    3.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0068   -2.0241    2.8297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5221   -0.3874    2.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5947   -1.8616    2.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9863   -1.2655    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3674   -2.9142    0.7985 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 23  2  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
 16 17  1  6
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12 10  1  0
 10 11  1  1
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24 19  1  0
 14 16  1  0
  8 10  1  0
 25  6  1  0
 22 50  1  0
 22 51  1  0
 22 52  1  0
 19 49  1  1
 18 47  1  0
 18 48  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 14 43  1  6
 13 41  1  0
 13 42  1  0
 12 39  1  0
 12 40  1  0
 11 36  1  0
 11 37  1  0
 11 38  1  0
  8 35  1  6
  7 33  1  0
  7 34  1  0
  6 32  1  1
  5 30  1  0
  5 31  1  0
  1 28  1  0
  1 29  1  0
 24 53  1  6
 26 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
M  END


  Mrv1652309072212572D          

 27 30  0  0  1  0            999 V2000
    2.6012   -2.4549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7296   -1.6400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0879   -1.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3180   -1.4177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2163   -0.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9862   -0.0100    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1145    0.8049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8845    1.1013    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6544    1.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261    0.5827    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0447    1.2243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2960    0.8790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9376    0.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8093   -0.4546    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.6810   -1.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0394   -0.7509    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3357   -1.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9110   -1.5659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1411   -1.8622    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0128   -2.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6544   -3.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5261   -4.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4243   -2.8994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4995   -1.3436    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6278   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4468   -0.6285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1685    0.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
 24  2  1  6  0  0  0
 24 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0248627

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H32O5/c1-12-15(24)9-14-10-18-21(5,27-18)8-7-17-22(6,26-17)11-16(25-13(2)23)19(12)20(14,3)4/h14,16-19H,1,7-11H2,2-6H3/t14-,16+,17+,18-,19-,21-,22-/m0/s1

> <INCHI_KEY>
HNPAHGHFONBTLV-PKAJHXTNSA-N

> <FORMULA>
C22H32O5

> <MOLECULAR_WEIGHT>
376.493

> <EXACT_MASS>
376.22497413

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
40.36492795746279

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,5S,8R,10S,12R,13S)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0^{3,5}.0^{8,10}]heptadecan-12-yl acetate

> <JCHEM_LOGP>
2.7697438960000005

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9017378931019793

> <JCHEM_POLAR_SURFACE_AREA>
68.43

> <JCHEM_REFRACTIVITY>
100.1696

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5S,8R,10S,12R,13S)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0^{3,5}.0^{8,10}]heptadecan-12-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       4.856  -4.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.095  -3.061   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.898  -2.093   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.460  -2.646   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.137  -0.572   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.574  -0.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.814   1.503   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.251   2.056   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.688   2.609   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.449   1.088   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.417   2.285   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.886   1.641   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.084   0.673   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.844  -0.849   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.605  -2.370   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.407  -1.402   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.960  -2.839   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.167  -2.923   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.730  -3.476   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.491  -4.997   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.688  -5.965   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.449  -7.487   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.125  -5.412   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.532  -2.508   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.772  -0.987   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.301  -1.173   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.781   0.176   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   10                                                       
CONECT   10    9    8   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15   14   17   18                                             
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19    2   25                                                  
CONECT   25   24    6   26   27                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₂O₅

Average Mass

376.4930 Da

Monoisotopic Mass

376.22497 Da

IUPAC Name

(1R,3S,5S,8R,10S,12R,13S)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0^{3,5}.0^{8,10}]heptadecan-12-yl acetate

Traditional Name

(1R,3S,5S,8R,10S,12R,13S)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0^{3,5}.0^{8,10}]heptadecan-12-yl acetate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H32O5/c1-12-15(24)9-14-10-18-21(5,27-18)8-7-17-22(6,26-17)11-16(25-13(2)23)19(12)20(14,3)4/h14,16-19H,1,7-11H2,2-6H3/t14-,16+,17+,18-,19-,21-,22-/m0/s1

InChI Key

HNPAHGHFONBTLV-PKAJHXTNSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carboxylic acid esters. These are carboxylic acid derivatives in which the carbon atom from the carbonyl group is attached to an alkyl or an aryl moiety through an oxygen atom (forming an ester group).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

Carboxylic acid esters

Alternative Parents

Substituents

Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.77	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.43 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.17 m³·mol⁻¹	ChemAxon
Polarizability	40.36 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00050802

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

139263050

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kim C, Ojo-Amaize E, Spencer B, Rockenstein E, Mante M, Desplats P, Wrasidlo W, Adame A, Nchekwube E, Oyemade O, Okogun J, Chan M, Cottam H, Masliah E: Hypoestoxide reduces neuroinflammation and alpha-synuclein accumulation in a mouse model of Parkinson's disease. J Neuroinflammation. 2015 Dec 18;12:236. doi: 10.1186/s12974-015-0455-9. [PubMed:26683203 ]
Stone AV, Loeser RF, Vanderman KS, Long DL, Clark SC, Ferguson CM: Pro-inflammatory stimulation of meniscus cells increases production of matrix metalloproteinases and additional catabolic factors involved in osteoarthritis pathogenesis. Osteoarthritis Cartilage. 2014 Feb;22(2):264-74. doi: 10.1016/j.joca.2013.11.002. Epub 2013 Dec 4. [PubMed:24315792 ]
McGrath NA, Lee CA, Araki H, Brichacek M, Njardarson JT: An efficient substrate-controlled approach towards hypoestoxide, a member of a family of diterpenoid natural products with an inside-out [9.3.1]bicyclic core. Angew Chem Int Ed Engl. 2008;47(49):9450-3. doi: 10.1002/anie.200804237. [PubMed:18979485 ]
Ojo-Amaize EA, Cottam HB, Oyemade OA, Okogun JI, Nchekwube EJ: Hypoestoxide inhibits tumor growth in the mouse CT26 colon tumor model. World J Gastroenterol. 2007 Sep 14;13(34):4586-8. doi: 10.3748/wjg.v13.i34.4586. [PubMed:17729410 ]
Ojo-Amaize EA, Nchekwube EJ, Cottam HB, Oyemade OA, Adesomoju AA, Okogun JI: Plasmodium berghei: antiparasitic effects of orally administered hypoestoxide in mice. Exp Parasitol. 2007 Oct;117(2):218-21. doi: 10.1016/j.exppara.2007.04.012. Epub 2007 May 10. [PubMed:17568581 ]
Donnelly LE, Rogers DF: Therapy for chronic obstructive pulmonary disease in the 21st century. Drugs. 2003;63(19):1973-98. doi: 10.2165/00003495-200363190-00002. [PubMed:12962514 ]
LOTUS database [Link]

Showing NP-Card for (1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate (NP0248627)

MOL for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

3D MOL for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

3D SDF for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

3D-SDF for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

PDB for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

3D PDB for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

SMILES for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

INCHI for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

Structure for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)

3D Structure for NP0248627 ((1r,3s,5s,8r,10s,12r,13s)-5,10,17,17-tetramethyl-14-methylidene-15-oxo-4,9-dioxatetracyclo[11.3.1.0³,⁵.0⁸,¹⁰]heptadecan-12-yl acetate)