NP-MRD: Showing NP-Card for chandonanone F (NP0043101)

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Record Information

Version

1.0

Created at

2021-06-21 00:35:52 UTC

Updated at

2021-06-30 00:18:35 UTC

NP-MRD ID

NP0043101

Secondary Accession Numbers

None

Natural Product Identification

Common Name

chandonanone F

Provided By

JEOL Database JEOL Logo

Description

CHEMBL3109418 belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. chandonanone F is found in Chandonanthu and Plicanthus hirtellus. It was first documented in 2002 (PMID: 29437326). Based on a literature review a significant number of articles have been published on CHEMBL3109418 (PMID: 27466641) (PMID: 27253005) (PMID: 26389468) (PMID: 26389426).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102353D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306212102353D          

 62 64  0  0  0  0            999 V2000
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   -0.7323    0.4613    2.4498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3115    1.1415    3.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -1.0530    2.5411 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9227   -1.5662    2.8657 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0506    0.9999    1.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804    2.2763    1.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    2.8593    2.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319    2.8309    3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377   -3.0742    2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2550   -1.6782    1.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779   -1.8016    3.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.1211    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -2.7095    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937   -1.9646   -0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381   -0.2871   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8593   -4.5290   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9874   -3.8673   -1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -4.1513   -2.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444   -2.7123   -4.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3868   -1.4304   -4.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9084   -3.1106   -4.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1602   -0.4058   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    3.7969   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345    2.5589   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271    2.8908   -2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905    2.8207   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    1.0777   -0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1760    3.0319    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429    2.5204    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    2.9456    2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    0.1575    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    1.0279    3.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263    1.4010    4.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.2832    3.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.7007    3.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -1.4517    3.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8281   -1.5263    1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -2.6629    2.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586   -1.2812    3.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 27  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  1  0  0  0  0
 21 20  1  0  0  0  0
  5  4  1  6  0  0  0
 20 19  1  0  0  0  0
 13 14  2  0  0  0  0
 19 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  0  0  0  0
 17 15  1  0  0  0  0
 17 18  1  6  0  0  0
  8  7  1  0  0  0  0
  5  6  1  0  0  0  0
 26 24  1  0  0  0  0
 15 45  1  1  0  0  0
 24 22  1  0  0  0  0
  4  2  1  0  0  0  0
 22 21  1  0  0  0  0
  2  1  1  0  0  0  0
  8  9  1  0  0  0  0
  2  3  2  0  0  0  0
 20 28  1  0  0  0  0
 15 13  1  0  0  0  0
 20 51  1  6  0  0  0
 13  9  1  0  0  0  0
 22 54  1  6  0  0  0
  7  5  1  0  0  0  0
 22 23  1  0  0  0  0
  9 10  2  3  0  0  0
 24 25  1  1  0  0  0
  7 35  1  0  0  0  0
  7 36  1  0  0  0  0
 27 61  1  0  0  0  0
 27 62  1  0  0  0  0
 26 59  1  0  0  0  0
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 21 52  1  0  0  0  0
 21 53  1  0  0  0  0
 19 49  1  0  0  0  0
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  8 37  1  0  0  0  0
  8 38  1  0  0  0  0
 11 39  1  0  0  0  0
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 11 41  1  0  0  0  0
 12 42  1  0  0  0  0
 12 43  1  0  0  0  0
 12 44  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
  6 32  1  0  0  0  0
  6 33  1  0  0  0  0
  6 34  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 23 55  1  0  0  0  0
 23 56  1  0  0  0  0
 23 57  1  0  0  0  0
 25 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043101

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12O[C@]([H])(C([H])([H])[C@]1([H])C([H])([H])[H])C([H])([H])[C@@]1(O[C@@]1([H])C(=O)C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@](OC(=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])C2([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O6/c1-13(2)17-7-8-20(5,26-15(4)23)9-10-22(25)14(3)11-16(27-22)12-21(6)19(28-21)18(17)24/h14,16,19,25H,7-12H2,1-6H3/t14-,16+,19-,20+,21-,22+/m0/s1

> <INCHI_KEY>
RVAPVOIDEZXMQO-RAXJWKBNSA-N

> <FORMULA>
C22H34O6

> <MOLECULAR_WEIGHT>
394.508

> <EXACT_MASS>
394.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.55526989521188

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3S,5R,10R,13R,14S)-13-hydroxy-3,10,14-trimethyl-6-oxo-7-(propan-2-ylidene)-4,16-dioxatricyclo[11.2.1.0^{3,5}]hexadecan-10-yl acetate

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
3.105050862999999

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.854408426369798

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.847821767612029

> <JCHEM_PKA_STRONGEST_BASIC>
-3.992916307113847

> <JCHEM_POLAR_SURFACE_AREA>
85.36000000000001

> <JCHEM_REFRACTIVITY>
104.7196

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3S,5R,10R,13R,14S)-13-hydroxy-3,10,14-trimethyl-6-oxo-7-(propan-2-ylidene)-4,16-dioxatricyclo[11.2.1.0^{3,5}]hexadecan-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    3.1122    2.3131    2.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.9237    2.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107    0.5427    4.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1117   -1.2238    1.9200 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3634   -1.9932    2.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577   -1.6353    0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8354   -1.2924   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -1.3529   -1.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -2.4398   -2.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6810   -3.8160   -2.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -2.4111   -4.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -0.0211   -2.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    0.6514   -3.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    0.4060   -2.1123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0662    1.4707   -2.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173    1.7748   -1.5099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2941    2.8070   -1.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0417    1.9501   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    2.1347    0.8133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0762    2.2135    1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    0.8073    2.1773 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1409    0.7347    3.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7323    0.4613    2.4498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3115    1.1415    3.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -1.0530    2.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227   -1.5662    2.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506    0.9999    1.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804    2.2763    1.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    2.8593    2.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319    2.8309    3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377   -3.0742    2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2550   -1.6782    1.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779   -1.8016    3.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.1211    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -2.7095    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937   -1.9646   -0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381   -0.2871   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8593   -4.5290   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9874   -3.8673   -1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -4.1513   -2.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444   -2.7123   -4.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3868   -1.4304   -4.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9084   -3.1106   -4.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1602   -0.4058   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    3.7969   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345    2.5589   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271    2.8908   -2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905    2.8207   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    1.0777   -0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1760    3.0319    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429    2.5204    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    2.9456    2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    0.1575    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    1.0279    3.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263    1.4010    4.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.2832    3.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.7007    3.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -1.4517    3.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8281   -1.5263    1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -2.6629    2.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586   -1.2812    3.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 27  1  0
 10 11  1  0
 10 12  1  0
 26 27  1  0
 24 28  1  0
 21 20  1  0
  5  4  1  6
 20 19  1  0
 13 14  2  0
 19 17  1  0
 15 16  1  0
 17 16  1  0
 17 15  1  0
 17 18  1  6
  8  7  1  0
  5  6  1  0
 26 24  1  0
 15 45  1  1
 24 22  1  0
  4  2  1  0
 22 21  1  0
  2  1  1  0
  8  9  1  0
  2  3  2  0
 20 28  1  0
 15 13  1  0
 20 51  1  6
 13  9  1  0
 22 54  1  6
  7  5  1  0
 22 23  1  0
  9 10  2  3
 24 25  1  1
  7 35  1  0
  7 36  1  0
 27 61  1  0
 27 62  1  0
 26 59  1  0
 26 60  1  0
 21 52  1  0
 21 53  1  0
 19 49  1  0
 19 50  1  0
  8 37  1  0
  8 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
  6 32  1  0
  6 33  1  0
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  1 29  1  0
  1 30  1  0
  1 31  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 25 58  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       3.112   2.313   2.559  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.717   0.924   2.955  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.611   0.543   4.112  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.450   0.185   1.853  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.112  -1.224   1.920  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.363  -1.993   2.384  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.758  -1.635   0.466  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.835  -1.292  -0.576  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.298  -1.353  -1.984  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.243  -2.440  -2.788  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.681  -3.816  -2.353  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.743  -2.411  -4.214  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.875  -0.021  -2.519  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.622   0.651  -3.219  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.511   0.406  -2.112  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.066   1.471  -2.888  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.217   1.775  -1.510  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.294   2.807  -1.354  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.042   1.950  -0.687  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.780   2.135   0.813  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.076   2.213   1.615  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.204   0.807   2.177  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.141   0.735   3.373  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.732   0.461   2.450  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.312   1.141   3.621  0.00  0.00           O+0
HETATM   26  C   UNK     0      -0.497  -1.053   2.541  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.923  -1.566   2.866  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.051   1.000   1.315  0.00  0.00           O+0
HETATM   29  H   UNK     0       3.880   2.276   1.782  0.00  0.00           H+0
HETATM   30  H   UNK     0       2.235   2.859   2.204  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.532   2.831   3.426  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.238  -3.074   2.261  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.255  -1.678   1.831  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.578  -1.802   3.441  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.839  -1.121   0.173  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.536  -2.709   0.426  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.694  -1.965  -0.466  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.238  -0.287  -0.401  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.859  -4.529  -2.481  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.987  -3.867  -1.306  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.527  -4.151  -2.963  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.544  -2.712  -4.897  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.387  -1.430  -4.539  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.908  -3.111  -4.332  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.160  -0.406  -1.855  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.859   3.797  -1.180  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.935   2.559  -0.502  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.927   2.891  -2.242  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.591   2.821  -1.067  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.691   1.078  -0.836  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.176   3.032   0.985  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.943   2.520   1.021  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.961   2.946   2.425  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.592   0.158   1.381  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.155   1.028   3.080  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.826   1.401   4.183  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.190  -0.283   3.772  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.479   0.701   3.976  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.146  -1.452   3.332  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.828  -1.526   1.609  0.00  0.00           H+0
HETATM   61  H   UNK     0       0.842  -2.663   2.900  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.159  -1.281   3.895  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2                                                       
CONECT    5   27    4    6    7                                             
CONECT    6    5   32   33   34                                             
CONECT    7    8    5   35   36                                             
CONECT    8    7    9   37   38                                             
CONECT    9    8   13   10                                                  
CONECT   10   11   12    9                                                  
CONECT   11   10   39   40   41                                             
CONECT   12   10   42   43   44                                             
CONECT   13   14   15    9                                                  
CONECT   14   13                                                            
CONECT   15   16   17   45   13                                             
CONECT   16   15   17                                                       
CONECT   17   19   16   15   18                                             
CONECT   18   17   46   47   48                                             
CONECT   19   20   17   49   50                                             
CONECT   20   21   19   28   51                                             
CONECT   21   20   22   52   53                                             
CONECT   22   24   21   54   23                                             
CONECT   23   22   55   56   57                                             
CONECT   24   28   26   22   25                                             
CONECT   25   24   58                                                       
CONECT   26   27   24   59   60                                             
CONECT   27    5   26   61   62                                             
CONECT   28   24   20                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33    6                                                            
CONECT   34    6                                                            
CONECT   35    7                                                            
CONECT   36    7                                                            
CONECT   37    8                                                            
CONECT   38    8                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   12                                                            
CONECT   43   12                                                            
CONECT   44   12                                                            
CONECT   45   15                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   20                                                            
CONECT   52   21                                                            
CONECT   53   21                                                            
CONECT   54   22                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   23                                                            
CONECT   58   25                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  128    0
END

RDKit          3D

62 64  0  0  0  0  0  0  0  0999 V2000
    3.1122    2.3131    2.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7175    0.9237    2.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107    0.5427    4.1117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4495    0.1851    1.8526 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1117   -1.2238    1.9200 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3634   -1.9932    2.3837 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7577   -1.6353    0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8354   -1.2924   -0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2983   -1.3529   -1.9845 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432   -2.4398   -2.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6810   -3.8160   -2.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -2.4111   -4.2143 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8750   -0.0211   -2.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6222    0.6514   -3.2191 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5111    0.4060   -2.1123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0662    1.4707   -2.8880 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2173    1.7748   -1.5099 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2941    2.8070   -1.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0417    1.9501   -0.6872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7803    2.1347    0.8133 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0762    2.2135    1.6153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2036    0.8073    2.1773 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1409    0.7347    3.3733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7323    0.4613    2.4498 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3115    1.1415    3.6209 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4972   -1.0530    2.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9227   -1.5662    2.8657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0506    0.9999    1.3145 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8804    2.2763    1.7820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    2.8593    2.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5319    2.8309    3.4261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2377   -3.0742    2.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2550   -1.6782    1.8309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5779   -1.8016    3.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385   -1.1211    0.1734 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5358   -2.7095    0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6937   -1.9646   -0.4662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381   -0.2871   -0.4008 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8593   -4.5290   -2.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9874   -3.8673   -1.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5266   -4.1513   -2.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5444   -2.7123   -4.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3868   -1.4304   -4.5390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9084   -3.1106   -4.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1602   -0.4058   -1.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8591    3.7969   -1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9345    2.5589   -0.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9271    2.8908   -2.2422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905    2.8207   -1.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6911    1.0777   -0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1760    3.0319    0.9850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9429    2.5204    1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612    2.9456    2.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5924    0.1575    1.3812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    1.0279    3.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8263    1.4010    4.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1897   -0.2832    3.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4794    0.7007    3.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1456   -1.4517    3.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8281   -1.5263    1.6085 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8418   -2.6629    2.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1586   -1.2812    3.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
  5 27  1  0
 10 11  1  0
 10 12  1  0
 26 27  1  0
 24 28  1  0
 21 20  1  0
  5  4  1  6
 20 19  1  0
 13 14  2  0
 19 17  1  0
 15 16  1  0
 17 16  1  0
 17 15  1  0
 17 18  1  6
  8  7  1  0
  5  6  1  0
 26 24  1  0
 15 45  1  1
 24 22  1  0
  4  2  1  0
 22 21  1  0
  2  1  1  0
  8  9  1  0
  2  3  2  0
 20 28  1  0
 15 13  1  0
 20 51  1  6
 13  9  1  0
 22 54  1  6
  7  5  1  0
 22 23  1  0
  9 10  2  3
 24 25  1  1
  7 35  1  0
  7 36  1  0
 27 61  1  0
 27 62  1  0
 26 59  1  0
 26 60  1  0
 21 52  1  0
 21 53  1  0
 19 49  1  0
 19 50  1  0
  8 37  1  0
  8 38  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 12 44  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
  6 32  1  0
  6 33  1  0
  6 34  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
 23 55  1  0
 23 56  1  0
 23 57  1  0
 25 58  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₃₄O₆

Average Mass

394.5080 Da

Monoisotopic Mass

394.23554 Da

IUPAC Name

(1R,3S,5R,10R,13R,14S)-13-hydroxy-3,10,14-trimethyl-6-oxo-7-(propan-2-ylidene)-4,16-dioxatricyclo[11.2.1.0^{3,5}]hexadecan-10-yl acetate

Traditional Name

(1R,3S,5R,10R,13R,14S)-13-hydroxy-3,10,14-trimethyl-6-oxo-7-(propan-2-ylidene)-4,16-dioxatricyclo[11.2.1.0^{3,5}]hexadecan-10-yl acetate

CAS Registry Number

Not Available

SMILES

[H]O[C@]12O[C@]([H])(C([H])([H])[C@]1([H])C([H])([H])[H])C([H])([H])[C@@]1(O[C@@]1([H])C(=O)C(=C(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@](OC(=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])C2([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H34O6/c1-13(2)17-7-8-20(5,26-15(4)23)9-10-22(25)14(3)11-16(27-22)12-21(6)19(28-21)18(17)24/h14,16,19,25H,7-12H2,1-6H3/t14-,16+,19-,20+,21-,22+/m0/s1

InChI Key

RVAPVOIDEZXMQO-RAXJWKBNSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, acetone-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, acetone-d6, 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
Chandonanthu	JEOL database	Li, R.-J., et al, J. Nat. Prod. 77, 339 (2014)
Plicanthus hirtellus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	2.1	ALOGPS
logP	3.11	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	11.85	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	104.72 m³·mol⁻¹	ChemAxon
Polarizability	42.56 Å³	ChemAxon
Number of Rings	3	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

Not Available

Chemspider ID

31130419

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

76317495

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Authors unspecified: Childhood Cancer Genomics (PDQ(R)): Health Professional Version. 2002. [PubMed:27466641 ]
Authors unspecified: Thyroid Cancer Screening (PDQ(R)): Patient Version. 2002. [PubMed:29437326 ]
Authors unspecified: Childhood Vascular Tumors Treatment (PDQ(R)): Patient Version. 2002. [PubMed:27253005 ]
Authors unspecified: Stomach (Gastric) Cancer Prevention (PDQ(R)): Patient Version. 2002. [PubMed:26389468 ]
Authors unspecified: Childhood Central Nervous System Atypical Teratoid/Rhabdoid Tumor Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389426 ]
Li, R.-J., et al. (2014). Li, R.-J., et al, J. Nat. Prod. 77, 339 (2014). J. Nat. Prod..

Showing NP-Card for chandonanone F (NP0043101)

MOL for NP0043101 (chandonanone F)

3D MOL for NP0043101 (chandonanone F)

3D SDF for NP0043101 (chandonanone F)

3D-SDF for NP0043101 (chandonanone F)

PDB for NP0043101 (chandonanone F)

3D PDB for NP0043101 (chandonanone F)

SMILES for NP0043101 (chandonanone F)

INCHI for NP0043101 (chandonanone F)

Structure for NP0043101 (chandonanone F)

3D Structure for NP0043101 (chandonanone F)