NP-MRD: Showing NP-Card for (2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate (NP0306635)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 23:14:14 UTC

Updated at

2022-09-10 23:14:15 UTC

NP-MRD ID

NP0306635

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate

Description

EUPACHINILIDE E belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. (2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate is found in Eupatorium chinense. (2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate was first documented in 2004 (PMID: 15387644). Based on a literature review very few articles have been published on EUPACHINILIDE E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201142D          

 29 32  0  0  1  0            999 V2000
   -0.2958   -1.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4982   -1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833   -0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246    0.2929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6077   -0.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320   -1.2187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6182   -1.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128   -2.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367   -2.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2550   -2.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513   -1.4008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9957   -0.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -0.9505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8117   -0.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940   -2.9502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4250   -3.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801   -3.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566   -4.0063    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -3.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774   -2.4995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3068   -2.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -3.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8170   -4.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5940   -3.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242   -4.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -3.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -3.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -4.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -1.6774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 15 19  1  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  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 29  1  0  0  0  0
 29  2  1  1  0  0  0
  6 29  1  0  0  0  0
M  END

     RDKit          3D

 54 57  0  0  0  0  0  0  0  0999 V2000
    1.0033   -1.2629   -3.3821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1093   -0.8946   -2.8039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4182   -1.5696   -3.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968   -2.3704   -3.9408 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2807   -1.1652   -2.0148 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5201   -0.4881   -1.0455 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4551    0.1821   -1.8612 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6931    0.6672   -1.0647 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3788   -0.2894   -0.3005 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7276   -0.5720   -0.3908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4150    0.0783   -1.2169 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3698   -1.6115    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183   -1.8512    0.2784 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -2.2430    1.2933 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0954   -3.3000    2.1835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4381   -3.4916    1.9884 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3494    1.8924   -0.2354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4418    1.7085    0.9739 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7621    3.0443    1.3860 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5090    1.2860    2.1134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3981    1.0439    3.6266 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.6924    0.9707    1.0065 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8806    1.7953    1.5447 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6421    1.0425    2.4149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7138    2.1602    0.3541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0068    2.8171   -0.6099 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0863    1.4948   -0.8814 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9672    1.0851   -2.0078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3213    0.4140   -0.1924 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9770   -0.8302   -3.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9657   -2.1181   -4.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0418   -1.2452   -0.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8751    1.0676   -2.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4393    1.0847   -1.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2195   -1.1639   -0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4333   -1.6045    1.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0627   -2.8732   -0.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5162   -1.9728    1.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5255   -4.2391    1.9804 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387   -2.9893    3.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8496   -4.0157    2.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0005    2.6523   -0.9497 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3659    2.2759    0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0908    3.5349    1.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2360    2.1106    2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0479    0.3726    1.8942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5794    0.1346    1.7613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5013    2.6813    2.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1729    1.6482    2.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8115    2.1925    0.4186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3738    0.9564   -2.9424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4665    0.1171   -1.8201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6808    1.9096   -2.2419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1589   -0.2592    0.2084 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8 17  1  0
 17 18  1  0
 18 19  1  1
 18 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  6
 27 29  1  0
 29  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2  7  1  0
  7  8  1  0
 29 22  1  0
  7  6  1  0
 27 25  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
  8 34  1  6
 17 42  1  0
 17 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  1
 23 48  1  1
 24 49  1  0
 25 50  1  1
 28 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  1
  6 32  1  1
  1 30  1  0
  1 31  1  0
  7 33  1  6
M  END


  Mrv1652309112201142D          

 29 32  0  0  1  0            999 V2000
   -0.2958   -1.3913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4982   -1.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7833   -0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3246    0.2929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6077   -0.4248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320   -1.2187    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6182   -1.4688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128   -2.2394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367   -2.1974    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2550   -2.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9513   -1.4008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9957   -0.5770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2601   -0.9505    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8117   -0.2580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4940   -2.9502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4250   -3.7723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2801   -3.2004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566   -4.0063    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.6771   -3.0660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0774   -2.4995    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3068   -2.7941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1766   -3.6087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8170   -4.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5940   -3.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7242   -4.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2345   -3.3833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -3.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1353   -4.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1463   -1.6774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 15 19  1  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  0  0  0  0
 24 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 20 29  1  0  0  0  0
 29  2  1  1  0  0  0
  6 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C(=C/CO)C(=O)O[C@@H]1C[C@](O)(CCl)C2[C@H](O)[C@H]3O[C@@]3(C)C2[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H25ClO8/c1-8(4-5-22)17(24)27-10-6-20(26,7-21)12-13(19(3)16(29-19)14(12)23)15-11(10)9(2)18(25)28-15/h4,10-16,22-23,26H,2,5-7H2,1,3H3/b8-4+/t10-,11-,12?,13?,14+,15+,16-,19+,20+/m1/s1

> <INCHI_KEY>
JNLCQVGOEVZPLZ-IANPJELBSA-N

> <FORMULA>
C20H25ClO8

> <MOLECULAR_WEIGHT>
428.86

> <EXACT_MASS>
428.1237955

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
41.79493688820335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,6R,7R,9R,11S,12R,14S)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-4-hydroxy-2-methylbut-2-enoate

> <JCHEM_LOGP>
-0.02091936699999901

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.075945812313282

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.374519297620328

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5521985964827207

> <JCHEM_POLAR_SURFACE_AREA>
125.82000000000001

> <JCHEM_REFRACTIVITY>
100.59919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,6R,7R,9R,11S,12R,14S)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-4-hydroxy-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.552  -2.597   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.930  -2.178   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.462  -0.733   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.606   0.547   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       3.001  -0.793   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       3.420  -2.275   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.887  -2.742   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.437  -4.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.975  -4.102   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       7.943  -5.300   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       7.376  -2.615   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.459  -1.077   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.085  -1.774   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.248  -0.482   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.655  -5.507   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.527  -7.042   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.123  -5.974   0.000  0.00  0.00           C+0
HETATM   18 Cl   UNK     0       6.452  -7.478   0.000  0.00  0.00          Cl+0
HETATM   19  C   UNK     0       3.131  -5.723   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.011  -4.666   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.573  -5.216   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       0.330  -6.736   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.525  -7.707   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.109  -7.286   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.352  -8.807   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.304  -6.315   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.743  -6.865   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.986  -8.386   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.140  -3.131   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   29                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   29                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11   13                                                       
CONECT   13   12    7   11   14                                             
CONECT   14   13                                                            
CONECT   15    8   16   17   19                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17                                                            
CONECT   19   15   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27                                                            
CONECT   29   20    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₅ClO₈

Average Mass

428.8600 Da

Monoisotopic Mass

428.12380 Da

IUPAC Name

(2S,6R,7R,9R,11S,12R,14S)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-4-hydroxy-2-methylbut-2-enoate

Traditional Name

(2S,6R,7R,9R,11S,12R,14S)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecan-7-yl (2E)-4-hydroxy-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C(=C/CO)C(=O)O[C@@H]1C[C@](O)(CCl)C2[C@H](O)[C@H]3O[C@@]3(C)C2[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C20H25ClO8/c1-8(4-5-22)17(24)27-10-6-20(26,7-21)12-13(19(3)16(29-19)14(12)23)15-11(10)9(2)18(25)28-15/h4,10-16,22-23,26H,2,5-7H2,1,3H3/b8-4+/t10-,11-,12?,13?,14+,15+,16-,19+,20+/m1/s1

InChI Key

JNLCQVGOEVZPLZ-IANPJELBSA-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
Eupatorium chinense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
Guaiane sesquiterpenoid
Fatty acid ester
Fatty acyl
Oxane
Gamma butyrolactone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Lactone
Halohydrin
Chlorohydrin
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Alkyl halide
Alkyl chloride
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	-0.021	ChemAxon
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.6 m³·mol⁻¹	ChemAxon
Polarizability	41.79 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023188

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

101731296

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Huo J, Yang SP, Ding J, Yue JM: Cytotoxic sesquiterpene lactones from Eupatorium lindleyanum. J Nat Prod. 2004 Sep;67(9):1470-5. doi: 10.1021/np040023h. [PubMed:15387644 ]
LOTUS database [Link]

Showing NP-Card for (2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate (NP0306635)

MOL for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D MOL for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D SDF for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D-SDF for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

PDB for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D PDB for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

SMILES for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

INCHI for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

Structure for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D Structure for NP0306635 ((2s,6r,7r,9r,11s,12r,14s)-9-(chloromethyl)-9,11-dihydroxy-14-methyl-5-methylidene-4-oxo-3,13-dioxatetracyclo[8.4.0.0²,⁶.0¹²,¹⁴]tetradecan-7-yl (2e)-4-hydroxy-2-methylbut-2-enoate)