NP-MRD: Showing NP-Card for 10-epi-Eupatoroxin (NP0051892)

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Record Information

Version

2.0

Created at

2022-04-27 23:05:49 UTC

Updated at

2022-04-27 23:05:49 UTC

NP-MRD ID

NP0051892

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-epi-Eupatoroxin

Description

10-Epi-Eupatoroxin belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). 10-epi-Eupatoroxin is found in Eupatorium rotundifolium. Based on a literature review very few articles have been published on 10-epi-Eupatoroxin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201052D          

 28 32  0  0  1  0            999 V2000
    2.5806    0.0401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3849    0.2237    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0299   -0.2907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0299   -1.1157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3849   -1.6301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5806   -1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -0.7032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5081   -1.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685   -2.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637   -2.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754   -2.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1473   -3.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -4.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404   -3.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5425   -4.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -1.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -2.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2994   -0.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -0.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -0.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    1.0454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7002    1.3696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1574    0.7483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3358    0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837    1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435    0.5479    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  6  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
  4 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  1  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  1  6  0  0  0
 23 26  1  1  0  0  0
 22 26  1  0  0  0  0
 22 27  1  6  0  0  0
  2 28  1  1  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    1.1242   -3.2318    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0512   -2.5694   -0.2627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2920   -3.1655   -0.4321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5484   -4.4111   -0.3661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832   -2.1110   -0.6707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6056   -1.0066   -0.0606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1463   -1.1587   -0.5437 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6499   -0.1523    0.1507 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0152   -0.4972    0.1119 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9978    0.2576   -0.5124 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6209    1.3186   -1.0759 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3840   -0.1680   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7567   -1.4263    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2943    0.5697   -1.1080 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0020    1.8270   -1.8034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2687    0.1487    1.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0522    0.7725    1.7724 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1365    1.6793    2.9914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7107    0.4248    2.9450 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7654    1.2991    0.5853 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1295    1.7782    1.0058 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5601    1.2778    2.2091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1129    1.3063   -0.0525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8191    1.7567   -1.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5093    0.4145   -0.8537 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0235   -0.6150   -1.8032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0396    0.3246   -0.5080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3686    0.7533   -1.6785 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -4.3008    0.2353 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0940   -2.7836    0.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5780   -1.1502    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1937   -0.9152   -1.6282 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5831    0.8212   -0.4163 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7843   -1.3189    0.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7246   -2.2384   -0.5755 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0402   -1.6162    1.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3385    0.2253   -1.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550    2.6099   -1.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2492   -2.2129 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917    1.6842   -2.6544 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567    0.8032    1.9892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3274   -0.8061    2.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7655    2.5708    2.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2143    1.8224    3.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2268    2.1995    0.1811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2034    2.8859    1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0872    1.9064    2.7559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1605    1.2704    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4474   -1.4529   -1.1837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848   -0.2543   -2.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2692   -0.9907   -2.5218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9287    1.3830   -2.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 12  2  0
 12 13  1  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  8  1  0
  8 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  6
 25 27  1  0
 27 28  1  6
 27  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
 17 19  1  1
 27 20  1  0
  7  6  1  0
 25 23  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
 14 37  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
  8 33  1  6
 16 41  1  0
 16 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  6
 21 46  1  1
 22 47  1  0
 23 48  1  1
 26 49  1  0
 26 50  1  0
 26 51  1  0
 28 52  1  0
  6 31  1  1
  1 29  1  0
  1 30  1  0
  7 32  1  6
M  END


  Mrv1652304282201052D          

 28 32  0  0  1  0            999 V2000
    2.5806    0.0401    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3849    0.2237    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0299   -0.2907    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0299   -1.1157    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3849   -1.6301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5806   -1.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2226   -0.7032    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5081   -1.1157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5081   -0.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5685   -2.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9637   -2.9955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1754   -2.7524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1473   -3.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9356   -4.0430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5404   -3.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5425   -4.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -1.3706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0695   -2.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2994   -0.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1244   -0.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8145   -0.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4588    1.0454    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7002    1.3696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1574    0.7483    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3358    0.8223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3603    1.8645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837    1.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1435    0.5479    0.0000 O   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  6  0  0  0
  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  6  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 13 16  1  0  0  0  0
  4 17  1  6  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  3 21  1  1  0  0  0
  2 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
  1 24  1  0  0  0  0
 24 25  1  6  0  0  0
 23 26  1  1  0  0  0
 22 26  1  0  0  0  0
 22 27  1  6  0  0  0
  2 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0051892

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(\C)C(=O)O[C@@H]1C[C@@]2(CO2)[C@@H]2[C@H](O)[C@H]3O[C@@]3(C)[C@]2(O)[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O8/c1-5-8(2)16(22)26-10-6-19(7-25-19)13-12(21)15-18(4,28-15)20(13,24)14-11(10)9(3)17(23)27-14/h5,10-15,21,24H,3,6-7H2,1-2,4H3/b8-5-/t10-,11-,12+,13+,14+,15-,18-,19-,20-/m1/s1

> <INCHI_KEY>
QUSNLLJZMPVTTC-MGJUGYCASA-N

> <FORMULA>
C20H24O8

> <MOLECULAR_WEIGHT>
392.404

> <EXACT_MASS>
392.147117733

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.37767622361549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'R,2S,2'S,6'R,7'R,10'R,11'S,12'R,14'R)-1',11'-dihydroxy-14'-methyl-5'-methylidene-4'-oxo-3',13'-dioxaspiro[oxirane-2,9'-tetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecane]-7'-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.77

> <JCHEM_LOGP>
0.5169548150000005

> <ALOGPS_LOGS>
-1.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.785147950175212

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.311405596722413

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3849248048923037

> <JCHEM_POLAR_SURFACE_AREA>
118.12

> <JCHEM_REFRACTIVITY>
93.14449999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'R,2S,2'S,6'R,7'R,10'R,11'S,12'R,14'R)-1',11'-dihydroxy-14'-methyl-5'-methylidene-4'-oxo-3',13'-dioxaspiro[oxirane-2,9'-tetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecane]-7'-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.817   0.075   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.318   0.418   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.522  -0.543   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.522  -2.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.318  -3.043   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.817  -2.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.149  -1.313   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.815  -2.083   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.815  -0.543   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.661  -4.544   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.532  -5.592   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.061  -5.138   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.875  -7.093   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.347  -7.547   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.475  -6.500   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.746  -8.141   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.987  -2.559   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.463  -4.023   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.892  -1.313   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.432  -1.313   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.987  -0.067   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.457   1.951   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.040   2.557   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.027   1.397   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.493   1.535   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       6.273   3.480   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       7.996   1.974   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       7.735   1.023   0.000  0.00  0.00           O+0
CONECT    1    2    7   24                                                  
CONECT    2    1    3   22   28                                             
CONECT    3    2    4   21                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8    9                                             
CONECT    8    7    9                                                       
CONECT    9    8    7                                                       
CONECT   10    5   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13                                                            
CONECT   17    4   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3                                                       
CONECT   22    2   23   26   27                                             
CONECT   23   22   24   26                                                  
CONECT   24   23    1   25                                                  
CONECT   25   24                                                            
CONECT   26   23   22                                                       
CONECT   27   22                                                            
CONECT   28    2                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₈

Average Mass

392.4040 Da

Monoisotopic Mass

392.14712 Da

IUPAC Name

(1'R,2S,2'S,6'R,7'R,10'R,11'S,12'R,14'R)-1',11'-dihydroxy-14'-methyl-5'-methylidene-4'-oxo-3',13'-dioxaspiro[oxirane-2,9'-tetracyclo[8.4.0.0^{2,6}.0^{12,14}]tetradecane]-7'-yl (2Z)-2-methylbut-2-enoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1C[C@@]2(CO2)[C@@H]2[C@H](O)[C@H]3O[C@@]3(C)[C@]2(O)[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C20H24O8/c1-5-8(2)16(22)26-10-6-19(7-25-19)13-12(21)15-18(4,28-15)20(13,24)14-11(10)9(3)17(23)27-14/h5,10-15,21,24H,3,6-7H2,1-2,4H3/b8-5-/t10-,11-,12+,13+,14+,15-,18-,19-,20-/m1/s1

InChI Key

QUSNLLJZMPVTTC-MGJUGYCASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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 rotundifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides).

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Ambrosanolides and secoambrosanolides

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:708 )
Guaianolide (C09447 )

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	0.77	ALOGPS
logP	0.52	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.31	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	118.12 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.14 m³·mol⁻¹	ChemAxon
Polarizability	38.38 Å³	ChemAxon
Number of Rings	5	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

C00003280

Chemspider ID

4444805

KEGG Compound ID

C09447

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281463

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 10-epi-Eupatoroxin (NP0051892)

MOL for NP0051892 (10-epi-Eupatoroxin)

3D MOL for NP0051892 (10-epi-Eupatoroxin)

3D SDF for NP0051892 (10-epi-Eupatoroxin)

3D-SDF for NP0051892 (10-epi-Eupatoroxin)

PDB for NP0051892 (10-epi-Eupatoroxin)

3D PDB for NP0051892 (10-epi-Eupatoroxin)

SMILES for NP0051892 (10-epi-Eupatoroxin)

INCHI for NP0051892 (10-epi-Eupatoroxin)

Structure for NP0051892 (10-epi-Eupatoroxin)

3D Structure for NP0051892 (10-epi-Eupatoroxin)