NP-MRD: Showing NP-Card for (1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate (NP0158172)

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Record Information

Version

2.0

Created at

2022-09-02 15:42:44 UTC

Updated at

2022-09-02 15:42:44 UTC

NP-MRD ID

NP0158172

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate

Description

Calealactone B belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. (1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate was first documented in 2004 (PMID: 15541738). Based on a literature review a small amount of articles have been published on Calealactone B (PMID: 32630070) (PMID: 30399497) (PMID: 29076166).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022217422D          

 30 32  0  0  1  0            999 V2000
    6.8812    4.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0861    4.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4978    4.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8794    3.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4677    2.7981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0844    3.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8776    2.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4660    1.7791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2894    1.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328    2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    1.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3903    0.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    0.5370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592    0.9804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4642    0.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759    1.3385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6692    0.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808    1.1182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2858    0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925    1.6965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6992    2.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    3.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943    2.7155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1393    3.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    3.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826    2.1371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2893    2.9358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010    3.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    4.3129    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    2.7098    1.9318   -2.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3409    1.6285   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7538    2.0379   -0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6192    0.8784   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2105    0.5869    0.9515 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3009    0.4798   -0.2749 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5793   -0.2630    0.7293 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4835    0.6627    1.2154 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1932    1.1529    2.5821 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3369    0.4897    3.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6272    2.5380    2.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547    3.3492    3.5741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2672    2.7946    1.3733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5684    1.9515    0.4789 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1308    1.9184   -0.9119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5718    1.8911   -1.0744 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9440    2.9147   -2.1797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3741    0.7111   -1.3223 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7162   -0.1374   -0.1689 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1014   -0.6015   -1.3323 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7962   -1.2556   -1.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1262   -1.2530   -2.2956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932   -1.9298   -0.0943 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1096   -3.4177   -0.5404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0635   -2.0080    0.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2016   -1.5720    0.2176 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6764   -2.6135    1.0992 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6022   -3.5501    0.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -4.5877    1.7161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0941   -3.5461   -0.3846 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6882    1.6325   -2.3901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2328    2.4885   -3.0059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8236    2.3756    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9764    2.8494   -1.6205 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4565    1.1741   -1.0864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3222   -0.3850    1.5480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4768    0.1930    1.3254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -0.5505    3.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156    0.9297    4.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4864    2.3670    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5096    1.2501   -1.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7687    2.9352   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0119    2.3960   -0.1532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9161    3.3739   -1.9757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0573    2.3353   -3.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1171    3.6170   -2.3412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201    1.0213   -1.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8258   -1.3241   -1.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1599   -3.7161   -0.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8051   -4.0471    0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4672   -3.5114   -1.4296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4982   -2.2310    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816   -1.7700   -0.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2310   -4.6845    2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1418   -5.5610    1.1691 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0159   -4.3396    2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11  9  1  0
  9 10  2  3
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  4  1  0
  4  5  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
  7 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 26 23  1  0
 23 24  1  0
 23 25  1  1
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  1  0
 19 18  1  0
 18 16  1  0
  8 14  1  0
 18 20  1  0
 17 44  1  0
 17 45  1  0
 17 46  1  0
 16 43  1  1
 15 41  1  0
 15 42  1  0
 14 40  1  6
 10 38  1  0
 10 39  1  0
  8 37  1  1
  7 36  1  1
  3 33  1  0
  3 34  1  0
  3 35  1  0
  1 31  1  0
  1 32  1  0
 26 53  1  6
 29 54  1  0
 29 55  1  0
 29 56  1  0
 24 49  1  0
 24 50  1  0
 24 51  1  0
 25 52  1  0
 20 48  1  6
 18 47  1  6
M  END


  Mrv1652309022217422D          

 30 32  0  0  1  0            999 V2000
    6.8812    4.3955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0861    4.1751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4978    4.7535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8794    3.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4677    2.7981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0844    3.1561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8776    2.3575    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4660    1.7791    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.2894    1.8293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7328    2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916    1.0617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3903    0.8549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    0.5370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592    0.9804    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4642    0.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759    1.3385    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6692    0.5398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0808    1.1182    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2858    0.8978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925    1.6965    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6992    2.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109    3.0736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943    2.7155    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1393    3.4602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1660    3.1945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826    2.1371    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2893    2.9358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7010    3.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9077    4.3129    0.0000 O   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  6  0  0  0
 23 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0158172

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1C[C@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)C(C)=C)[C@@H](OC(C)=O)[C@@](C)(O)C(=O)[C@H]2O[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C21H26O9/c1-8(2)19(24)30-15-13-10(4)20(25)28-12(13)7-9(3)14-16(29-14)17(23)21(6,26)18(15)27-11(5)22/h9,12-16,18,26H,1,4,7H2,2-3,5-6H3/t9-,12-,13+,14+,15+,16+,18-,21+/m1/s1

> <INCHI_KEY>
BRBRVKOYZAMSBL-PXFMFDQNSA-N

> <FORMULA>
C21H26O9

> <MOLECULAR_WEIGHT>
422.43

> <EXACT_MASS>
422.157682417

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
41.125944272570536

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,4S,6S,8R,9R,10S,11S)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradecan-10-yl 2-methylprop-2-enoate

> <ALOGPS_LOGP>
0.91

> <JCHEM_LOGP>
2.019746230999999

> <ALOGPS_LOGS>
-2.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.434428559231844

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.139251959575407

> <JCHEM_PKA_STRONGEST_BASIC>
-4.05008732990438

> <JCHEM_POLAR_SURFACE_AREA>
128.73000000000002

> <JCHEM_REFRACTIVITY>
99.89730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3R,4S,6S,8R,9R,10S,11S)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradecan-10-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      12.845   8.205   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.361   7.794   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.263   8.873   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.975   6.303   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      12.073   5.223   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.491   5.891   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.105   4.401   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.203   3.321   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.740   3.415   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.568   4.713   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.304   1.982   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      13.795   1.596   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      11.116   1.002   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.817   1.830   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.333   1.419   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.235   2.498   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.849   1.008   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.751   2.087   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.267   1.676   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       4.653   3.167   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.039   4.658   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.940   5.737   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       6.523   5.069   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.860   6.459   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       7.777   5.963   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.621   3.989   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       8.007   5.480   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.909   6.560   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.424   6.149   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.294   8.051   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18   20                                                       
CONECT   20   19   18   21                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23    7   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₆O₉

Average Mass

422.4300 Da

Monoisotopic Mass

422.15768 Da

IUPAC Name

(1R,3R,4S,6S,8R,9R,10S,11S)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradecan-10-yl 2-methylprop-2-enoate

Traditional Name

(1R,3R,4S,6S,8R,9R,10S,11S)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0^{4,6}]tetradecan-10-yl 2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

C[C@@H]1C[C@H]2OC(=O)C(=C)[C@@H]2[C@H](OC(=O)C(C)=C)[C@@H](OC(C)=O)[C@@](C)(O)C(=O)[C@H]2O[C@@H]12

InChI Identifier

InChI=1S/C21H26O9/c1-8(2)19(24)30-15-13-10(4)20(25)28-12(13)7-9(3)14-16(29-14)17(23)21(6,26)18(15)27-11(5)22/h9,12-16,18,26H,1,4,7H2,2-3,5-6H3/t9-,12-,13+,14+,15+,16+,18-,21+/m1/s1

InChI Key

BRBRVKOYZAMSBL-PXFMFDQNSA-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 germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Tricarboxylic acid or derivatives
Acyloin
Cyclitol or derivatives
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Ketone
Lactone
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen 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	0.91	ALOGPS
logP	2.02	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	12.14	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	128.73 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	99.9 m³·mol⁻¹	ChemAxon
Polarizability	41.13 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

C00035816

Chemspider ID

8399525

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11464346

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Caldas LA, Rodrigues MT, Batista ANL, Batista JM Jr, Lago JHG, Ferreira MJP, Rubio IGS, Sartorelli P: Sesquiterpene Lactones from Calea pinnatifida: Absolute Configuration and Structural Requirements for Antitumor Activity. Molecules. 2020 Jun 30;25(13):3005. doi: 10.3390/molecules25133005. [PubMed:32630070 ]
Gogineni V, Nael MA, Leon F, Nunez MJ, Cutler SJ: Computationally aided stereochemical assignment of undescribed bisabolenes from Calea urticifolia. Phytochemistry. 2019 Jan;157:145-150. doi: 10.1016/j.phytochem.2018.10.022. Epub 2018 Nov 3. [PubMed:30399497 ]
Sanchez-Mendoza ME, Lopez-Lorenzo Y, Matus-Meza AS, Arrieta J: Gastroprotective effect of calealactone B: Lack of involvement of prostaglandins, nitric oxide and sulfhydryls. Drug Dev Res. 2018 Feb;79(1):11-15. doi: 10.1002/ddr.21415. Epub 2017 Oct 26. [PubMed:29076166 ]
Yamada M, Matsuura N, Suzuki H, Kurosaka C, Hasegawa N, Ubukata M, Tanaka T, Iinuma M: Germacranolides from Calea urticifolia. Phytochemistry. 2004 Dec;65(23):3107-11. doi: 10.1016/j.phytochem.2004.08.040. [PubMed:15541738 ]
LOTUS database [Link]

Showing NP-Card for (1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate (NP0158172)

MOL for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

3D MOL for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

3D SDF for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

3D-SDF for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

PDB for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

3D PDB for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

SMILES for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

INCHI for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

Structure for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)

3D Structure for NP0158172 ((1r,3r,4s,6s,8r,9r,10s,11s)-9-(acetyloxy)-8-hydroxy-3,8-dimethyl-12-methylidene-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]tetradecan-10-yl 2-methylprop-2-enoate)