NP-MRD: Showing NP-Card for eupaformosanin (NP0189992)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-04 06:35:07 UTC

Updated at

2022-09-04 06:35:08 UTC

NP-MRD ID

NP0189992

Secondary Accession Numbers

None

Natural Product Identification

Common Name

eupaformosanin

Description

Eupaformosanin 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. eupaformosanin is found in Ageratina palmeri, Bahia ambrosioides, Chaenactis douglasii, Disynaphia multicrenulata, Eupatorium cannabinum, Eupatorium glehni and Urolepis hecatantha. eupaformosanin was first documented in 2022 (PMID: 35469839). Based on a literature review very few articles have been published on Eupaformosanin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042208352D          

 30 31  0  0  1  0            999 V2000
    0.2172   -2.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -2.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908   -0.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732   -0.9274    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7639   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -0.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5580    0.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3331   -0.2781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8239    0.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6436    0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1344    0.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9725   -0.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -1.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9772   -2.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273   -2.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -2.4240    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2541   -3.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5830   -3.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923   -4.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4027   -3.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316   -4.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513   -4.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421   -4.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7132   -3.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -1.7524    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  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 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  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  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30  2  1  1  0  0  0
  6 30  1  0  0  0  0
M  END

     RDKit          3D

 58 59  0  0  0  0  0  0  0  0999 V2000
    1.9615    1.2270    2.8501 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9192    1.3410    2.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3470    2.5621    1.5003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8724    3.6929    1.5696 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8701    2.2970    0.8964 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0012    0.8769    0.7267 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3406    0.5128    1.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3893    0.2329    0.5048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6670   -0.1152    1.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2400    0.2798   -0.9729 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5590    0.3590   -1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9893    1.4015   -2.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3721    1.4186   -2.8583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2207    2.3438   -2.5512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5912   -0.9703   -1.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2400   -1.9123   -0.4303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339   -2.0911    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8404   -3.0868    1.1595 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1973   -1.4087   -0.4175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9121   -0.7578    0.7479 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1581   -0.2350    0.2984 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3779   -0.7387    0.6991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3898   -1.7049    1.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6645   -0.2073    0.2419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6120    0.8007   -0.5921 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7893    1.4785   -1.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7666    1.3756   -2.5815 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9193   -0.8068    0.7057 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9704   -0.6792    2.1090 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984    0.2275    1.4938 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3194    0.2689    3.2024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162    2.0858    3.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    0.7033   -0.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4363    0.4822    2.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9437    0.6864    1.8996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5911   -1.0586    1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4984   -0.1660    0.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228    1.2096   -1.3083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3065    1.3299   -3.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9608    0.5506   -2.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8371    2.3789   -2.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2990   -1.5385   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7323   -0.7302   -2.1890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0989   -2.4743   -0.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707   -2.6084    2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7027   -3.7937    1.1934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0673   -3.6662    0.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0828   -0.7565   -1.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8918   -2.2377   -0.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1693   -1.5993    1.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188    1.1765   -0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6397    2.5689   -0.9487 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7437    1.1970   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5953    0.9021   -2.8133 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8164   -0.4831    0.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8264   -1.9175    0.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3753    0.0365    2.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3668   -0.2598    2.4024 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  2  0
 12 11  1  0
 11 10  1  0
 10 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 28  1  0
 28 29  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 20 30  1  0
 30  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
  2 30  1  0
 13 39  1  0
 13 40  1  0
 13 41  1  0
 10 38  1  1
 15 42  1  0
 15 43  1  0
 16 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 19 49  1  0
 20 50  1  1
 28 55  1  0
 28 56  1  0
 29 57  1  0
 25 51  1  0
 26 52  1  0
 26 53  1  0
 27 54  1  0
 30 58  1  1
  6 33  1  6
  1 31  1  0
  1 32  1  0
  7 34  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
M  END


  Mrv1652309042208352D          

 30 31  0  0  1  0            999 V2000
    0.2172   -2.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4791   -2.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.3287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8249   -1.3214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4908   -0.6656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732   -0.9274    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7639   -0.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508   -0.0162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5580    0.8087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3331   -0.2781    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8239    0.3851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6436    0.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1344    0.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9725   -0.4650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8121   -0.9498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3214   -1.6129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -2.4379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9772   -2.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5273   -2.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7449   -2.4240    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2541   -3.0872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5830   -3.8438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0923   -4.5069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4027   -3.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7316   -4.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5513   -4.7873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421   -4.1242    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8935   -3.2741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7132   -3.3676    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2659   -1.7524    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  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 10 15  1  0  0  0  0
 15 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  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  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 24 28  1  0  0  0  0
 28 29  1  0  0  0  0
 20 30  1  0  0  0  0
 30  2  1  1  0  0  0
  6 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0189992

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C\C=C(C)\C[C@@H](OC(=O)C(\CO)=C\CO)[C@@H]2[C@H](OC(=O)C2=C)\C=C1\C

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10-,16-7+/t17-,18-,19-,20-/m1/s1

> <INCHI_KEY>
XYPJAWWDSQFSQA-OZZXCXKDSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.15566432543683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,9R,11aR)-9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

> <JCHEM_LOGP>
1.3327141113333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.648577036263198

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.791780275384095

> <JCHEM_PKA_STRONGEST_BASIC>
-2.557857287039238

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
109.56329999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
eupaformosanin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       0.405  -5.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.894  -3.734   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -2.480   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.540  -2.467   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.916  -1.242   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.377  -1.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.293  -0.493   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.761  -0.030   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.775   1.510   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.222  -0.519   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.138   0.719   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.668   0.544   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.584   1.782   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.282  -0.868   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.116  -1.773   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.200  -3.011   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.186  -4.551   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.424  -5.467   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.718  -5.014   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.257  -4.525   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       2.341  -5.763   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.955  -7.175   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.039  -8.413   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.485  -7.350   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.099  -8.762   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.629  -8.936   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.545  -7.698   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.401  -6.112   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.931  -6.286   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.363  -3.271   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   30                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   10   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   24   29                                                       
CONECT   29   28                                                            
CONECT   30   20    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   62    0
END

View in JSmol

Synonyms

Value	Source
Eupaformosanin, (3ar-(3ar,4R(e)),6E,9S,10Z,11ar)-isomer	MeSH

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(3aR,4R,9R,11aR)-9-(acetyloxy)-6,10-dimethyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2E)-4-hydroxy-2-(hydroxymethyl)but-2-enoate

Traditional Name

eupaformosanin

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C\C=C(C)\C[C@@H](OC(=O)C(\CO)=C\CO)[C@@H]2[C@H](OC(=O)C2=C)\C=C1\C

InChI Identifier

InChI=1S/C22H28O8/c1-12-5-6-17(28-15(4)25)13(2)10-19-20(14(3)21(26)29-19)18(9-12)30-22(27)16(11-24)7-8-23/h5,7,10,17-20,23-24H,3,6,8-9,11H2,1-2,4H3/b12-5+,13-10-,16-7+/t17-,18-,19-,20-/m1/s1

InChI Key

XYPJAWWDSQFSQA-OZZXCXKDSA-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
Ageratina palmeri	LOTUS Database	35616633
Bahia ambrosioides	LOTUS Database	35616633
Chaenactis douglasii	LOTUS Database	35616633
Disynaphia multicrenulata	LOTUS Database	35616633
Eupatorium cannabinum	LOTUS Database	35616633
Eupatorium glehni	LOTUS Database	35616633
Urolepis hecatantha	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
Germacrane sesquiterpenoid
Sesquiterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Hydroxy acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Primary alcohol
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

germacranolide (CHEBI:4927 )
Germacrenes (C09432 )

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	1.33	ChemAxon
pKa (Strongest Acidic)	14.79	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	109.56 m³·mol⁻¹	ChemAxon
Polarizability	43.16 Å³	ChemAxon
Number of Rings	2	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

C00003270

Chemspider ID

4444796

KEGG Compound ID

C09432

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281453

PDB ID

Not Available

ChEBI ID

4927

Good Scents ID

Not Available

References

General References

Wei Y, Zhu Z, Hu H, Guan J, Yang B, Zhao H: Eupaformosanin induces apoptosis and ferroptosis through ubiquitination of mutant p53 in triple-negative breast cancer. Eur J Pharmacol. 2022 Jun 5;924:174970. doi: 10.1016/j.ejphar.2022.174970. Epub 2022 Apr 22. [PubMed:35469839 ]
LOTUS database [Link]

Showing NP-Card for eupaformosanin (NP0189992)

MOL for NP0189992 (eupaformosanin)

3D MOL for NP0189992 (eupaformosanin)

3D SDF for NP0189992 (eupaformosanin)

3D-SDF for NP0189992 (eupaformosanin)

PDB for NP0189992 (eupaformosanin)

3D PDB for NP0189992 (eupaformosanin)

SMILES for NP0189992 (eupaformosanin)

INCHI for NP0189992 (eupaformosanin)

Structure for NP0189992 (eupaformosanin)

3D Structure for NP0189992 (eupaformosanin)