NP-MRD: Showing NP-Card for (1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate (NP0240503)

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Record Information

Version

2.0

Created at

2022-09-07 00:20:49 UTC

Updated at

2022-09-07 00:20:49 UTC

NP-MRD ID

NP0240503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate

Description

(1S,2R,4R,6R,7Z,9Z,11R,14S)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]Tetradeca-7,9-dien-2-yl (2E)-2-(hydroxymethyl)but-2-enoate 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. (1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate is found in Liatris acidota. Based on a literature review very few articles have been published on (1S,2R,4R,6R,7Z,9Z,11R,14S)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]Tetradeca-7,9-dien-2-yl (2E)-2-(hydroxymethyl)but-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072202202D          

 28 30  0  0  1  0            999 V2000
    2.0294    2.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213    1.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6535    2.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736    2.9983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2133    0.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    0.1853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -0.5907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9736   -0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6562   -1.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9675   -0.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4683   -1.1733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9361   -1.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7064   -2.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0549   -3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2303   -3.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006   -3.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5477   -2.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678   -1.8891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4432   -1.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8148   -0.6335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2435   -0.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3470   -0.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0671    0.7731    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -1.0968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 28 24  1  1  0  0  0
 20 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  END

     RDKit          3D

 53 55  0  0  0  0  0  0  0  0999 V2000
    5.4936    1.5406   -0.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0833    1.0108   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3917    0.8993    0.6800 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0532    1.3132    1.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2921    2.3366    2.4939 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0282    0.3953    0.7073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4037    0.3048    1.8200 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.0068   -0.4142 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0030   -0.4983   -0.3931 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2053   -2.0089   -0.5731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9682   -2.8361    0.0752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5873   -4.0425    0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6672   -1.8588    0.7145 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -2.4046   -0.4646 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5610   -2.4643   -0.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1567   -1.4890    0.3294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020   -0.3100    0.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9660    0.0029    2.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7940    0.5830    0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3084    0.5354   -0.9569 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5768    1.8687   -1.4578 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4471    2.4768   -1.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3680    3.5828   -2.4355 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055    1.6279   -1.4708 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2250    2.1728   -0.3113 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6744    1.6500   -2.6033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838    3.3271   -2.8463 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8962    0.2237   -1.2402 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8109    1.6663   -1.4631 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5355    2.5390    0.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1853    0.8255    0.0663 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6158    0.7116   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1023    1.5666    1.8001 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0296    0.4743    2.6973 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8269    3.0191    2.9371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2996   -0.4232    0.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0926   -2.3233   -0.0323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1651   -2.2578   -1.6439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4883   -4.9585    0.2458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3712   -4.2268    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555   -3.8083    1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9398   -2.1237   -1.5516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0982   -3.3178   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2738   -1.5814    0.4153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2290   -0.4806    3.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0075   -0.3545    2.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464    1.0700    2.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4524    1.4396    1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0451   -0.0168   -1.6000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4355    2.5477    0.2980 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5418    0.9990   -2.5003 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1445    1.2816   -3.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8524   -0.2002   -2.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 24 28  1  0
 28  9  1  0
 14 11  1  0
 28 20  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  0
  4 33  1  0
  4 34  1  0
  5 35  1  0
  9 36  1  1
 10 37  1  0
 10 38  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
 14 42  1  6
 15 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  6
 25 50  1  0
 26 51  1  0
 26 52  1  0
 28 53  1  6
M  END


  Mrv1652309072202202D          

 28 30  0  0  1  0            999 V2000
    2.0294    2.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3093    1.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1213    1.5918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6535    2.2223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3736    2.9983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4013    0.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2133    0.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8691    0.1853    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1490   -0.5907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9736   -0.5643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6562   -1.0277    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9675   -0.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4683   -1.1733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9361   -1.8037    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.7064   -2.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0549   -3.1021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2303   -3.1285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0006   -3.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5477   -2.6652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2678   -1.8891    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4432   -1.9155    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1633   -1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -0.9098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8148   -0.6335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2435   -0.0383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3470   -0.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0671    0.7731    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.4975   -1.0968    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 28 24  1  1  0  0  0
 20 28  1  0  0  0  0
  9 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0240503

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H25ClO7/c1-4-12(9-22)17(23)26-14-8-19(3)15(28-19)6-5-11(2)7-13-16(14)20(25,10-21)18(24)27-13/h4-7,13-16,22,25H,8-10H2,1-3H3/b6-5-,11-7-,12-4+/t13-,14-,15-,16-,19-,20+/m1/s1

> <INCHI_KEY>
BIFNFWDORRWVPK-HARQWDQXSA-N

> <FORMULA>
C20H25ClO7

> <MOLECULAR_WEIGHT>
412.86

> <EXACT_MASS>
412.1288808

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
40.69060192594643

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,4R,6R,7Z,9Z,11R,14S)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradeca-7,9-dien-2-yl (2E)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_LOGP>
1.6694012366666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.886423565304657

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.29990670220675

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8485306422682326

> <JCHEM_POLAR_SURFACE_AREA>
105.59000000000002

> <JCHEM_REFRACTIVITY>
102.8626

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4R,6R,7Z,9Z,11R,14S)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradeca-7,9-dien-2-yl (2E)-2-(hydroxymethyl)but-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       3.788   4.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.311   3.243   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.826   2.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.820   4.148   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       6.297   5.597   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.349   1.523   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       7.865   1.251   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       5.356   0.346   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.878  -1.103   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.417  -1.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.692  -1.918   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.273  -0.492   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.207  -2.190   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.214  -3.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.785  -4.846   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.569  -5.791   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.030  -5.840   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.601  -7.319   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.756  -4.975   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.233  -3.526   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.694  -3.576   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.171  -2.127   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.692  -1.698   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.388  -1.182   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.321  -0.072   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.381  -0.006   0.000  0.00  0.00           C+0
HETATM   27 Cl   UNK     0       3.859   1.443   0.000  0.00  0.00          Cl+0
HETATM   28  C   UNK     0       4.662  -2.047   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   11   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26   28                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   24   20    9                                                  
MASTER        0    0    0    0    0    0    0    0   28    0   60    0
END

View in JSmol

Synonyms

Value	Source
(1S,2R,4R,6R,7Z,9Z,11R,14S)-14-(Chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0,]tetradeca-7,9-dien-2-yl (2E)-2-(hydroxymethyl)but-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₅ClO₇

Average Mass

412.8600 Da

Monoisotopic Mass

412.12888 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C\C=C(/CO)C(=O)O[C@@H]1C[C@@]2(C)O[C@@H]2\C=C/C(/C)=C\[C@H]2OC(=O)[C@](O)(CCl)[C@@H]12

InChI Identifier

InChI=1S/C20H25ClO7/c1-4-12(9-22)17(23)26-14-8-19(3)15(28-19)6-5-11(2)7-13-16(14)20(25,10-21)18(24)27-13/h4-7,13-16,22,25H,8-10H2,1-3H3/b6-5-,11-7-,12-4+/t13-,14-,15-,16-,19-,20+/m1/s1

InChI Key

BIFNFWDORRWVPK-HARQWDQXSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Liatris acidota	LOTUS Database	35616633

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
Beta-hydroxy acid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Alkyl chloride
Organochloride
Organooxygen compound
Alkyl halide
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organohalogen compound
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

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

162891483

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate (NP0240503)

MOL for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D MOL for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D SDF for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D-SDF for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

PDB for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D PDB for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

SMILES for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

INCHI for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

Structure for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)

3D Structure for NP0240503 ((1s,2r,4r,6r,7z,9z,11r,14s)-14-(chloromethyl)-14-hydroxy-4,9-dimethyl-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradeca-7,9-dien-2-yl (2e)-2-(hydroxymethyl)but-2-enoate)