NP-MRD: Showing NP-Card for 3-epi-heliangin (NP0044052)

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Record Information

Version

1.0

Created at

2021-11-12 23:47:25 UTC

Updated at

2021-11-26 17:44:52 UTC

NP-MRD ID

NP0044052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-epi-heliangin

Description

3-Epi-heliangin 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. It was first documented in 2005 (PMID: 15921421). Based on a literature review very few articles have been published on 3-epi-heliangin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100472D          

 29 31  0  0  1  0            999 V2000
    4.2575    0.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8458    1.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6391    2.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274    2.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0207    3.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    2.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6408    1.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    0.0649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2592   -0.1554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4660   -0.9541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2894   -1.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916   -0.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3903   -0.0299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8776   -1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943   -1.8905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7010   -2.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6992   -1.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925   -0.8715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0808   -0.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3012    0.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759   -0.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2858   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -1.0782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6709   -0.7338    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1371    0.6605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  2  7  2  0  0  0  0
  8  1  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  8 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 26  1  0  0  0  0
 22 27  1  6  0  0  0
 10 28  1  1  0  0  0
  9 29  1  6  0  0  0
M  END

     RDKit          3D

 52 54  0  0  0  0  0  0  0  0999 V2000
    1.2752    3.3524    1.6434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659    2.7421    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0887    3.2318   -0.3873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4681    4.0111   -1.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3349    2.6468   -0.5794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3015    1.3437    0.0374 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6934    1.1203    0.5270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4725    0.1054    0.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8434    0.0300    0.7655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0611   -0.9717   -0.7579 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1761   -1.4272   -1.5048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -2.2012   -0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8692   -1.8055    1.2247 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3037   -2.7290    2.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4438   -1.8620    1.2199 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4203   -2.7765    0.4359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1619   -0.8043    2.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427    0.4078    1.3788 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3111    0.1634    0.1764 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6428    0.4341   -0.0843 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3025    0.9459    0.8520 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.1641   -1.3521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6015   -0.4376   -2.5127 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5787    0.4703   -1.4717 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3550    0.2369   -2.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3775    1.4865    1.1826 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7478    4.2701    1.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.9465    2.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9914    0.6789   -0.7612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0423    1.9004    1.2306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6212   -0.1428   -0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1307    0.9716    1.2770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9379   -0.7730    1.5199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3406   -0.6312   -1.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6574   -2.0540   -0.9038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3729   -2.9036    0.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8949   -2.7471   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3629   -0.9776    1.7731 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0175   -3.7660    0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -2.9309    0.8546 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5928   -2.2957   -0.5717 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9982   -1.2674    2.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5717   -0.4754    2.8552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3754    0.8642    2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5581   -0.6409   -2.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7060    0.3035   -3.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1621   -1.3374   -2.8460 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198    0.9185   -0.6234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7442    0.4690   -3.6191 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2351    0.8941   -2.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7402   -0.8204   -2.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9649    1.6693    2.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  1  0
 20 22  1  0
 22 24  2  0
 24 25  1  0
 22 23  1  0
 20 21  2  0
 19 18  1  0
 18 26  1  0
 26  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 15  1  0
 15 16  1  6
 15 17  1  0
 15 14  1  0
 17 18  1  0
  2 26  1  0
 14 13  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 18 44  1  1
 26 52  1  1
  6 29  1  6
  1 27  1  0
  1 28  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  6
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  1
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
M  END


  Mrv1652311132100472D          

 29 31  0  0  1  0            999 V2000
    4.2575    0.8636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8458    1.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6391    2.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274    2.8190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0207    3.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8440    2.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6408    1.2216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4642    0.0649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2592   -0.1554    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4660   -0.9541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.2894   -1.0043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5916   -0.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3903   -0.0299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    0.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0052    1.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8776   -1.5325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0826   -1.3121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4459   -0.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4943   -1.8905    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7010   -2.6892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6992   -1.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4925   -0.8715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0808   -0.2932    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3012    0.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8759   -0.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2858   -0.0728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6938   -1.0782    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6709   -0.7338    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1371    0.6605    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  2  7  2  0  0  0  0
  8  1  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  0  0  0
 23 25  1  0  0  0  0
  8 25  1  0  0  0  0
 23 26  1  0  0  0  0
 22 26  1  0  0  0  0
 22 27  1  6  0  0  0
 10 28  1  1  0  0  0
  9 29  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@H](O)\C(C)=C\[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@@H](C[C@@]1(C)O2)OC(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7+/t13-,14-,15-,16-,17+,20-/m1/s1

> <INCHI_KEY>
DZTWAOVNNLDWNH-DRCJWTCISA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.422

> <EXACT_MASS>
362.172938557

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
37.75035245070579

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4R,6R,8R,9E,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
2.406761494000001

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.524404543248814

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006825452782963

> <JCHEM_POLAR_SURFACE_AREA>
85.36

> <JCHEM_REFRACTIVITY>
95.53570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6R,8R,9E,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  O   UNK     0       7.947   1.612   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.046   2.692   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.660   4.182   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.758   5.262   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.372   6.753   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.176   4.594   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.530   2.280   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.333   0.121   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.817  -0.290   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.203  -1.781   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      11.740  -1.875   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      12.304  -0.442   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      13.795  -0.056   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.116   0.538   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.210   2.075   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.105  -2.861   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.621  -2.449   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.432  -1.470   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.523  -3.529   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.909  -5.020   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.039  -3.118   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.653  -1.627   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.751  -0.547   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.162   0.937   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.235  -0.958   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.267  -0.136   0.000  0.00  0.00           O+0
HETATM   27  H   UNK     0       3.162  -2.013   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.719  -1.370   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       9.589   1.233   0.000  0.00  0.00           H+0
CONECT    1    2    8                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    2                                                            
CONECT    8    1    9   25                                                  
CONECT    9    8   10   14   29                                             
CONECT   10    9   11   16   28                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    9   15                                                  
CONECT   15   14                                                            
CONECT   16   10   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   26   27                                             
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23    8                                                       
CONECT   26   23   22                                                       
CONECT   27   22                                                            
CONECT   28   10                                                            
CONECT   29    9                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
10-Epoxy-6betah,7alphah-helianga-4Z,11(13)-dien-6,12-olide	ChEBI
8beta-Tigloyloxy-3alpha-hydroxy-1alpha,10-epoxy-6betah,7alphah-helianga-4Z,11(13)-dien-6,12-olide	ChEBI
8b-Tigloyloxy-3a-hydroxy-1a,10-epoxy-6betah,7alphah-helianga-4Z,11(13)-dien-6,12-olide	Generator
8Β-tigloyloxy-3α-hydroxy-1α,10-epoxy-6betah,7alphah-helianga-4Z,11(13)-dien-6,12-olide	Generator

Chemical Formula

C₂₀H₂₆O₆

Average Mass

362.4220 Da

Monoisotopic Mass

362.17294 Da

IUPAC Name

(1R,2R,4R,6R,8R,9E,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

Traditional Name

(1R,2R,4R,6R,8R,9E,11R)-8-hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@H](O)\C(C)=C\[C@@]3([H])OC(=O)C(=C)[C@]3([H])[C@@H](C[C@@]1(C)O2)OC(=O)C(\C)=C\C

InChI Identifier

InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7+/t13-,14-,15-,16-,17+,20-/m1/s1

InChI Key

DZTWAOVNNLDWNH-DRCJWTCISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, 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

Eupatorium kiirunense

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

epoxide (CHEBI:65881 )
enoate ester (CHEBI:65881 )
sesquiterpene lactone (CHEBI:65881 )

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	1.45	ALOGPS
logP	2.41	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.54 m³·mol⁻¹	ChemAxon
Polarizability	37.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00042125

Chemspider ID

9828172

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11653434

PDB ID

Not Available

ChEBI ID

65881

Good Scents ID

Not Available

References

General References

Shen YC, Lo KL, Kuo YH, Khalil AT: Cytotoxic sesquiterpene lactones from Eupatorium kiirunense, a coastal plant of Taiwan. J Nat Prod. 2005 May;68(5):745-50. doi: 10.1021/np040214k. [PubMed:15921421 ]

Showing NP-Card for 3-epi-heliangin (NP0044052)

MOL for NP0044052 (3-epi-heliangin)

3D MOL for NP0044052 (3-epi-heliangin)

3D SDF for NP0044052 (3-epi-heliangin)

3D-SDF for NP0044052 (3-epi-heliangin)

PDB for NP0044052 (3-epi-heliangin)

3D PDB for NP0044052 (3-epi-heliangin)

SMILES for NP0044052 (3-epi-heliangin)

INCHI for NP0044052 (3-epi-heliangin)

Structure for NP0044052 (3-epi-heliangin)

3D Structure for NP0044052 (3-epi-heliangin)