NP-MRD: Showing NP-Card for (1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 (NP0246937)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 08:34:04 UTC

Updated at

2022-09-07 08:34:04 UTC

NP-MRD ID

NP0246937

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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

EUPACHNILIDE F 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. (1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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. Based on a literature review very few articles have been published on EUPACHNILIDE F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072210342D          

 32 35  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  2  0  0  0  0  0  0  0  0  0
    2.9128   -2.2394    0.0000 C   0  0  1  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
    5.0700   -2.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884   -3.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3668   -1.9415    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
  7 16  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32  2  1  1  0  0  0
  6 32  1  0  0  0  0
M  END

     RDKit          3D

 59 62  0  0  0  0  0  0  0  0999 V2000
    2.9375   -1.1838   -1.8900 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6414   -1.3573   -1.7874 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9880   -2.6671   -1.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4390   -3.8208   -1.6871 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524   -2.3696   -2.0910 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6715   -1.1615   -1.4243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8805   -0.5823   -2.0845 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4603    0.6042   -1.3635 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5015    0.1116   -0.4272 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1327   -0.0610    0.8990 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9104    0.4318    1.9238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5890    0.2901    3.3664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9815    1.0533    1.6111 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8673   -1.2386   -1.0220 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2229   -1.0376   -2.4468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9885   -1.5805   -2.0873 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7170   -3.0361   -2.3736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370    1.5293   -0.8069 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7024    2.0109   -1.9262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209    2.7639   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694    3.4775   -1.3950 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.9921    0.1967 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8109    0.6411   -0.5304 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7877    0.2463    0.4108 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9169    0.9984    0.7034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0346    2.0862    0.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9111    0.5634    1.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7375   -0.7195    2.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9866    1.2798    1.9588 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0132    0.8442    2.9587 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2699    0.7106    2.3303 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5660   -0.3534   -1.6184 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5862   -2.0209   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3442   -0.1964   -1.8563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8518   -1.4460   -0.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6163   -0.3394   -3.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0041    1.1931   -2.1651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4683    0.6986   -0.4696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325    1.2645    3.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344    0.1041    3.9221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9289   -0.5708    3.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6399   -1.8527   -0.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2762   -3.5641   -1.4808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661   -3.2207   -3.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7230   -3.5184   -2.5063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3065    2.2220   -2.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2846    3.5230   -0.1571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5045    2.6482    0.7672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2007    1.8360    0.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8295    0.1914    0.8448 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945    1.6044   -1.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6094   -0.5887    3.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8054   -1.1907    2.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6305   -1.3356    2.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0885    2.2115    1.4192 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1261    1.6622    3.6987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7216   -0.0600    3.4864 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2583    1.1427    1.4196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.1374   -2.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  2  0
 11 10  1  0
 10  9  1  0
  9 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16  7  1  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 32  1  0
 32 23  1  0
 23 22  1  0
 22 18  1  0
 18 19  1  6
 18 20  1  0
 20 21  1  0
 18  8  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 27 29  2  0
 29 30  1  0
 30 31  1  0
  8  9  1  0
 16 14  1  0
  8  7  1  0
 32  6  1  0
 12 39  1  0
 12 40  1  0
 12 41  1  0
  9 38  1  1
 14 42  1  1
 17 43  1  0
 17 44  1  0
 17 45  1  0
  7 36  1  6
  6 35  1  1
  1 33  1  0
  1 34  1  0
 32 59  1  6
 23 51  1  6
 22 49  1  0
 22 50  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
  8 37  1  6
 28 52  1  0
 28 53  1  0
 28 54  1  0
 29 55  1  0
 30 56  1  0
 30 57  1  0
 31 58  1  0
M  END


  Mrv1652309072210342D          

 32 35  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  2  0  0  0  0  0  0  0  0  0
    2.9128   -2.2394    0.0000 C   0  0  1  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
    5.0700   -2.7113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5884   -3.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3668   -1.9415    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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
  7 16  1  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  1  0  0  0
 20 21  1  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 23 32  1  0  0  0  0
 32  2  1  1  0  0  0
  6 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246937

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H27ClO9/c1-9(5-6-24)19(26)30-12-7-22(28,8-23)15-14(16-13(12)10(2)20(27)31-16)21(4)18(32-21)17(15)29-11(3)25/h5,12-18,24,28H,2,6-8H2,1,3-4H3/b9-5+/t12-,13-,14+,15+,16+,17+,18-,21+,22+/m1/s1

> <INCHI_KEY>
CXXLXCCCYXUUOP-ROZFHUFVSA-N

> <FORMULA>
C22H27ClO9

> <MOLECULAR_WEIGHT>
470.9

> <EXACT_MASS>
470.1343601

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
46.02102976146193

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,6R,7R,9R,10S,11S,12R,14S)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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>
0.42020604333333456

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.568651325497726

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.610335969618653

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5521985964827456

> <JCHEM_POLAR_SURFACE_AREA>
131.89

> <JCHEM_REFRACTIVITY>
109.75069999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,6R,7R,9R,10S,11S,12R,14S)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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                                 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      -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       9.464  -5.061   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.432  -6.259   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.018  -3.624   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.376  -2.615   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       7.459  -1.077   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.085  -1.774   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.248  -0.482   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.655  -5.507   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.527  -7.042   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.123  -5.974   0.000  0.00  0.00           C+0
HETATM   21 Cl   UNK     0       6.452  -7.478   0.000  0.00  0.00          Cl+0
HETATM   22  C   UNK     0       3.131  -5.723   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.011  -4.666   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.573  -5.216   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.330  -6.736   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.525  -7.707   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -1.109  -7.286   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.352  -8.807   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.304  -6.315   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.743  -6.865   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.986  -8.386   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.140  -3.131   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   32                                                  
CONECT    7    6    8   16                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14   16                                                       
CONECT   16   15    7   14   17                                             
CONECT   17   16                                                            
CONECT   18    8   19   20   22                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   18   23                                                       
CONECT   23   22   24   32                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   23    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇ClO₉

Average Mass

470.9000 Da

Monoisotopic Mass

470.13436 Da

IUPAC Name

(1S,2S,6R,7R,9R,10S,11S,12R,14S)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H27ClO9/c1-9(5-6-24)19(26)30-12-7-22(28,8-23)15-14(16-13(12)10(2)20(27)31-16)21(4)18(32-21)17(15)29-11(3)25/h5,12-18,24,28H,2,6-8H2,1,3-4H3/b9-5+/t12-,13-,14+,15+,16+,17+,18-,21+,22+/m1/s1

InChI Key

CXXLXCCCYXUUOP-ROZFHUFVSA-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
Guaiane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Oxane
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Tetrahydrofuran
Enoate ester
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Oxirane
Ether
Oxacycle
Primary alcohol
Alkyl chloride
Alcohol
Organooxygen compound
Alkyl halide
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organochloride
Organohalogen 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	0.42	ChemAxon
pKa (Strongest Acidic)	13.61	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	131.89 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.75 m³·mol⁻¹	ChemAxon
Polarizability	46.02 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	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

10188987

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21578013

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 (NP0246937)

MOL for NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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 NP0246937 ((1s,2s,6r,7r,9r,10s,11s,12r,14s)-11-(acetyloxy)-9-(chloromethyl)-9-hydroxy-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)