NP-MRD: Showing NP-Card for 2,3-epoxycalealactone A (NP0027775)

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Record Information

Version

2.0

Created at

2021-06-19 19:50:35 UTC

Updated at

2021-06-29 23:54:06 UTC

NP-MRD ID

NP0027775

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3-epoxycalealactone A

Provided By

JEOL Database JEOL Logo

Description

2,3-epoxycalealactone A is found in Calea urticifolia. 2,3-epoxycalealactone A was first documented in 2004 (Yamada, M., et al.). Based on a literature review very few articles have been published on (1R,3R,4S,6S,8S,9R,10S,11S)-8-hydroxy-3,8-dimethyl-12-methylidene-9-[(2-methylpropanoyl)oxy]-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0⁴,⁶]Tetradecan-10-yl 2-methylprop-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192121503D          

 62 64  0  0  0  0            999 V2000
    0.8790   -2.4826    4.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898   -1.6887    3.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430   -1.6026    2.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -0.8743    2.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -0.8773    3.3640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0823   -0.1577    1.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    0.6749    1.1075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3684    2.0686    0.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1818    2.7004    2.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    3.4317    2.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3721    2.6104    3.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947    1.8966    0.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0223   -2.2713    2.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0492   -1.8866    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3763    4.1232   -0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
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 23 24  1  0  0  0  0
  8  7  1  0  0  0  0
 21 22  2  0  0  0  0
  7 26  1  0  0  0  0
  9 10  2  3  0  0  0
  8 14  1  0  0  0  0
 11 12  2  0  0  0  0
 26 27  1  0  0  0  0
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 18 16  1  0  0  0  0
  6  4  1  0  0  0  0
 21 23  1  0  0  0  0
  4  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192121503D          

 62 64  0  0  0  0            999 V2000
    0.8790   -2.4826    4.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898   -1.6887    3.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2961   -0.4286   -1.7939 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1302    2.7156    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694    3.8431    3.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    3.6333    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376    1.1242   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690    3.0797   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763    4.1232   -0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498    3.9719   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2848   -0.0792    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771   -0.1374   -2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5346   -5.1530   -0.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0116   -4.5527    1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0  0  0  0
 23 24  1  0  0  0  0
  8  7  1  0  0  0  0
 21 22  2  0  0  0  0
  7 26  1  0  0  0  0
  9 10  2  3  0  0  0
  8 14  1  0  0  0  0
 11 12  2  0  0  0  0
 26 27  1  0  0  0  0
 20 21  1  0  0  0  0
 23 25  1  6  0  0  0
 18 16  1  0  0  0  0
  6  4  1  0  0  0  0
 21 23  1  0  0  0  0
  4  2  1  0  0  0  0
 20 18  1  0  0  0  0
  4  5  2  0  0  0  0
 14 13  1  0  0  0  0
 27 28  1  0  0  0  0
 13 11  1  0  0  0  0
 28 30  1  0  0  0  0
 11  9  1  0  0  0  0
 28 29  2  0  0  0  0
  2  1  2  3  0  0  0
 23 26  1  0  0  0  0
  2  3  1  0  0  0  0
 16 17  1  0  0  0  0
 30 31  1  0  0  0  0
 15 14  1  0  0  0  0
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  7  6  1  0  0  0  0
 20 19  1  0  0  0  0
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  8  9  1  0  0  0  0
 20 50  1  6  0  0  0
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  7 38  1  1  0  0  0
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  1 33  1  0  0  0  0
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 31 59  1  0  0  0  0
 32 60  1  0  0  0  0
 32 61  1  0  0  0  0
 32 62  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027775

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H30O9/c1-9(2)20(25)31-16-14-12(6)22(27)29-13(14)8-11(5)15-17(30-15)18(24)23(7,28)19(16)32-21(26)10(3)4/h10-11,13-17,19,28H,1,6,8H2,2-5,7H3/t11-,13-,14+,15+,16+,17+,19-,23-/m1/s1

> <INCHI_KEY>
KNCNIIMORRCROK-FXCGHDBCSA-N

> <FORMULA>
C23H30O9

> <MOLECULAR_WEIGHT>
450.484

> <EXACT_MASS>
450.188982546

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
44.99969274753778

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.95

> <JCHEM_LOGP>
3.263268356333333

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.434426017399087

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.139222858844015

> <JCHEM_PKA_STRONGEST_BASIC>
-4.050100058800102

> <JCHEM_POLAR_SURFACE_AREA>
128.73000000000002

> <JCHEM_REFRACTIVITY>
109.09870000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.42e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
    0.8790   -2.4826    4.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3684    2.0686    0.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1818    2.7004    2.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    3.4317    2.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348    2.4238    2.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3721    2.6104    3.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2037    3.2518   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    3.6128   -1.9721 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6526    4.7857   -2.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2961   -0.4286   -1.7939 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.0196   -1.3954    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1221   -4.1521   -0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0223   -2.2713    2.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1690    3.0797   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7498    3.9719   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060    5.1006   -3.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    5.6486   -2.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    4.5101   -3.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    2.0214   -3.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3612    0.5704   -3.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6969    1.5878    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2848   -0.0792    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5942   -5.0498    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356   -4.3608   -1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -3.3556   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5346   -5.1530   -0.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -5.7512    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116   -4.5527    1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 23 24  1  0
  8  7  1  0
 21 22  2  0
  7 26  1  0
  9 10  2  3
  8 14  1  0
 11 12  2  0
 26 27  1  0
 20 21  1  0
 23 25  1  6
 18 16  1  0
  6  4  1  0
 21 23  1  0
  4  2  1  0
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  4  5  2  0
 14 13  1  0
 27 28  1  0
 13 11  1  0
 28 30  1  0
 11  9  1  0
 28 29  2  0
  2  1  2  3
 23 26  1  0
  2  3  1  0
 16 17  1  0
 30 31  1  0
 15 14  1  0
 30 32  1  0
  7  6  1  0
 20 19  1  0
 18 19  1  0
  8  9  1  0
 20 50  1  6
 18 49  1  6
 16 45  1  1
 15 43  1  0
 15 44  1  0
 26 55  1  6
  7 38  1  1
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 17 46  1  0
 17 47  1  0
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 25 54  1  0
 30 56  1  1
  1 33  1  0
  1 34  1  0
  3 35  1  0
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  3 37  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 32 61  1  0
 32 62  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0       0.879  -2.483   4.240  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.990  -1.689   3.161  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.243  -1.603   2.346  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.195  -0.874   2.772  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.263  -0.877   3.364  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.082  -0.158   1.654  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.981   0.675   1.107  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.368   2.069   0.794  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.182   2.700   2.033  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.460   3.432   2.951  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.635   2.424   2.094  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.372   2.610   3.042  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.995   1.897   0.891  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.908   2.014  -0.050  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.204   3.252  -0.918  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.144   3.613  -1.972  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.653   4.786  -2.821  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.184   2.443  -2.864  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.346   2.644  -3.680  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.424   1.577  -2.723  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.430   1.774  -1.638  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.907   2.881  -1.400  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.810   0.529  -0.826  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.964   0.826   0.138  0.00  0.00           C+0
HETATM   25  O   UNK     0      -3.296  -0.429  -1.794  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.579  -0.093  -0.110  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.020  -1.395   0.386  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.297  -2.486   0.007  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.295  -2.452  -0.694  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.916  -3.740   0.592  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.122  -4.152  -0.242  0.00  0.00           C+0
HETATM   32  C   UNK     0      -0.886  -4.864   0.667  0.00  0.00           C+0
HETATM   33  H   UNK     0       1.706  -3.100   4.575  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.038  -2.533   4.822  0.00  0.00           H+0
HETATM   35  H   UNK     0       2.646  -0.586   2.365  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.022  -2.271   2.728  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.049  -1.887   1.307  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.764   0.806   1.863  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.130   2.716   0.362  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.069   3.843   3.807  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.524   3.633   2.878  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.938   1.124  -0.685  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.169   3.080  -1.415  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.376   4.123  -0.272  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.750   3.972  -1.455  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.106   5.101  -3.545  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.893   5.649  -2.191  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.552   4.510  -3.383  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.688   2.021  -3.352  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.361   0.570  -3.125  0.00  0.00           H+0
HETATM   51  H   UNK     0      -3.697   1.588   0.878  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.843   1.193  -0.406  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.285  -0.079   0.665  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.177  -0.137  -2.095  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.788  -0.251  -0.849  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.233  -3.513   1.617  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.594  -5.050   0.170  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.836  -4.361  -1.279  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.874  -3.356  -0.264  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.535  -5.153  -0.330  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.313  -5.751   1.146  0.00  0.00           H+0
HETATM   62  H   UNK     0      -0.012  -4.553   1.248  0.00  0.00           H+0
CONECT    1    2   33   34                                                  
CONECT    2    4    1    3                                                  
CONECT    3    2   35   36   37                                             
CONECT    4    6    2    5                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    8   26    6   38                                             
CONECT    8    7   14    9   39                                             
CONECT    9   10   11    8                                                  
CONECT   10    9   40   41                                                  
CONECT   11   12   13    9                                                  
CONECT   12   11                                                            
CONECT   13   14   11                                                       
CONECT   14    8   13   15   42                                             
CONECT   15   16   14   43   44                                             
CONECT   16   15   18   17   45                                             
CONECT   17   16   46   47   48                                             
CONECT   18   16   20   19   49                                             
CONECT   19   20   18                                                       
CONECT   20   21   18   19   50                                             
CONECT   21   22   20   23                                                  
CONECT   22   21                                                            
CONECT   23   24   25   21   26                                             
CONECT   24   23   51   52   53                                             
CONECT   25   23   54                                                       
CONECT   26    7   27   23   55                                             
CONECT   27   26   28                                                       
CONECT   28   27   30   29                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   56                                             
CONECT   31   30   57   58   59                                             
CONECT   32   30   60   61   62                                             
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    3                                                            
CONECT   38    7                                                            
CONECT   39    8                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   17                                                            
CONECT   49   18                                                            
CONECT   50   20                                                            
CONECT   51   24                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   25                                                            
CONECT   55   26                                                            
CONECT   56   30                                                            
CONECT   57   31                                                            
CONECT   58   31                                                            
CONECT   59   31                                                            
CONECT   60   32                                                            
CONECT   61   32                                                            
CONECT   62   32                                                            
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
    0.8790   -2.4826    4.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9898   -1.6887    3.1613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2430   -1.6026    2.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1948   -0.8743    2.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2631   -0.8773    3.3640 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0823   -0.1577    1.6538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9806    0.6749    1.1075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3684    2.0686    0.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1818    2.7004    2.0327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4600    3.4317    2.9507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6348    2.4238    2.0943 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3721    2.6104    3.0421 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9947    1.8966    0.8914 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9083    2.0143   -0.0499 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2037    3.2518   -0.9179 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1438    3.6128   -1.9721 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6526    4.7857   -2.8207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837    2.4435   -2.8641 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3463    2.6445   -3.6802 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4242    1.5765   -2.7226 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4303    1.7741   -1.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066    2.8808   -1.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8097    0.5291   -0.8258 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9639    0.8262    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2961   -0.4286   -1.7939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5791   -0.0929   -0.1101 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0196   -1.3954    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967   -2.4856    0.0066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2947   -2.4523   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9155   -3.7401    0.5921 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1221   -4.1521   -0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862   -4.8642    0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7064   -3.0998    4.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0375   -2.5331    4.8225 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6463   -0.5855    2.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0223   -2.2713    2.7278 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0492   -1.8866    1.3068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7641    0.8055    1.8634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1302    2.7156    0.3620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694    3.8431    3.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5236    3.6333    2.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9376    1.1242   -0.6853 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690    3.0797   -1.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3763    4.1232   -0.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498    3.9719   -1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060    5.1006   -3.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8934    5.6486   -2.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5518    4.5101   -3.3828 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6877    2.0214   -3.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3612    0.5704   -3.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6969    1.5878    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8427    1.1929   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2848   -0.0792    0.6648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1771   -0.1374   -2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7877   -0.2513   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2330   -3.5128    1.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5942   -5.0498    0.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8356   -4.3608   -1.2787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8739   -3.3556   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5346   -5.1530   -0.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3133   -5.7512    1.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0116   -4.5527    1.2482 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 15  1  0
 23 24  1  0
  8  7  1  0
 21 22  2  0
  7 26  1  0
  9 10  2  3
  8 14  1  0
 11 12  2  0
 26 27  1  0
 20 21  1  0
 23 25  1  6
 18 16  1  0
  6  4  1  0
 21 23  1  0
  4  2  1  0
 20 18  1  0
  4  5  2  0
 14 13  1  0
 27 28  1  0
 13 11  1  0
 28 30  1  0
 11  9  1  0
 28 29  2  0
  2  1  2  3
 23 26  1  0
  2  3  1  0
 16 17  1  0
 30 31  1  0
 15 14  1  0
 30 32  1  0
  7  6  1  0
 20 19  1  0
 18 19  1  0
  8  9  1  0
 20 50  1  6
 18 49  1  6
 16 45  1  1
 15 43  1  0
 15 44  1  0
 26 55  1  6
  7 38  1  1
  8 39  1  6
 14 42  1  6
 17 46  1  0
 17 47  1  0
 17 48  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 10 40  1  0
 10 41  1  0
 25 54  1  0
 30 56  1  1
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
 31 57  1  0
 31 58  1  0
 31 59  1  0
 32 60  1  0
 32 61  1  0
 32 62  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R,3R,4S,6S,8S,9R,10S,11S)-8-Hydroxy-3,8-dimethyl-12-methylidene-9-[(2-methylpropanoyl)oxy]-7,13-dioxo-5,14-dioxatricyclo[9.3.0.0,]tetradecan-10-yl 2-methylprop-2-enoic acid	Generator

Chemical Formula

C₂₃H₃₀O₉

Average Mass

450.4840 Da

Monoisotopic Mass

450.18898 Da

IUPAC Name

(1R,3R,4S,6S,8S,9R,10S,11S)-8-hydroxy-3,8-dimethyl-12-methylidene-9-[(2-methylpropanoyl)oxy]-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,8S,9R,10S,11S)-8-hydroxy-3,8-dimethyl-12-methylidene-9-[(2-methylpropanoyl)oxy]-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

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

InChI Identifier

InChI=1S/C23H30O9/c1-9(2)20(25)31-16-14-12(6)22(27)29-13(14)8-11(5)15-17(30-15)18(24)23(7,28)19(16)32-21(26)10(3)4/h10-11,13-17,19,28H,1,6,8H2,2-5,7H3/t11-,13-,14+,15+,16+,17+,19-,23-/m1/s1

InChI Key

KNCNIIMORRCROK-FXCGHDBCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Calea urticifolia	JEOL database	Yamada, M., et al, Phytochemistry 65, 3107 (2004)

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
Gamma butyrolactone
Cyclitol or derivatives
Acyloin
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	0.95	ALOGPS
logP	3.26	ChemAxon
logS	-3.1	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	6	ChemAxon
Refractivity	109.1 m³·mol⁻¹	ChemAxon
Polarizability	45 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59733837

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yamada, M., et al. (2004). Yamada, M., et al, Phytochemistry 65, 3107 (2004). Phytochem..

Showing NP-Card for 2,3-epoxycalealactone A (NP0027775)

MOL for NP0027775 (2,3-epoxycalealactone A)

3D MOL for NP0027775 (2,3-epoxycalealactone A)

3D SDF for NP0027775 (2,3-epoxycalealactone A)

3D-SDF for NP0027775 (2,3-epoxycalealactone A)

PDB for NP0027775 (2,3-epoxycalealactone A)

3D PDB for NP0027775 (2,3-epoxycalealactone A)

SMILES for NP0027775 (2,3-epoxycalealactone A)

INCHI for NP0027775 (2,3-epoxycalealactone A)

Structure for NP0027775 (2,3-epoxycalealactone A)

3D Structure for NP0027775 (2,3-epoxycalealactone A)