NP-MRD: Showing NP-Card for Euparotin (NP0044148)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

1.0

Created at

2021-11-12 23:52:42 UTC

Updated at

2021-11-26 17:45:57 UTC

NP-MRD ID

NP0044148

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Euparotin

Description

EUPAROTIN 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. Euparotin is found in Centaurea aggregata and Eupatorium rotundifolium. It was first documented in 1967 (PMID: 6031638). Based on a literature review very few articles have been published on EUPAROTIN (PMID: 4244949).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100522D          

 27 30  0  0  1  0            999 V2000
    4.9833    3.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1950    3.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902    2.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8019    3.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    1.8437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2293    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2293   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5801   -1.6570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0373   -2.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2787   -1.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5940   -1.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5704   -2.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4017   -1.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  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
 10 12  1  1  0  0  0
 13 10  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  1  0  0  0
 17 25  1  1  0  0  0
 16 26  1  0  0  0  0
 14 27  1  6  0  0  0
M  END

     RDKit          3D

 51 54  0  0  0  0  0  0  0  0999 V2000
    0.3745   -0.2398    3.3252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4660    0.2969    2.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835    1.4777    2.6927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2437    2.3003    3.6423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1753    1.5373    1.6185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5232    1.0001    0.4732 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7730   -0.1555    1.0749 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4300   -0.5324    0.2550 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5898    0.1687    0.5567 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556   -0.5183    0.9433 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7727   -1.7694    1.0232 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9501    0.2327    1.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8917    1.7237    1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0664   -0.3320    1.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1866   -1.7931    1.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0086   -0.3523   -1.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417   -1.2583   -1.5139 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9018   -2.4006   -2.3474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7743   -2.6035   -0.9371 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4638   -0.8298   -0.9940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4863   -0.7100   -2.1080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5176   -1.7743   -2.9675 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0813    0.5672   -2.7355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321    1.3304   -1.7986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0275    2.7094   -2.1202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5451    0.5994   -0.5126 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8503    0.7784    0.0081 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9504   -1.1188    3.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4855    0.2127    4.2881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8409    1.8124    0.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4880   -0.9985    1.1867 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6085   -1.6151    0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9066    2.1070    1.0237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417    2.1089    2.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3165    1.9956    0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9278    0.3250    1.8343 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2473   -2.0410    2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0158   -2.2456    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4880   -2.2228    2.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9118   -0.7025   -1.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1143    0.6865   -1.4796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5954   -3.0849   -2.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1210   -2.4637   -2.8278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8590   -1.5314   -0.2032 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4996   -0.5498   -1.6589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4430   -1.8445   -3.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2228    0.8057   -3.7776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8879    3.3973   -2.3030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4390    3.1423   -1.3110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4620    2.6800   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8088    1.6922    0.4262 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 23  1  0
 23 24  2  0
 24 26  1  0
 26  6  1  0
  6  7  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
 26 27  1  1
 24 25  1  0
 21 22  1  0
  7  8  1  0
 17 19  1  1
 26 20  1  0
  5  6  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 14 36  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
  8 32  1  6
 16 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  1
 21 45  1  1
 23 47  1  0
  6 30  1  6
  7 31  1  1
  1 28  1  0
  1 29  1  0
 27 51  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
 22 46  1  0
M  END


  Mrv1652311132100522D          

 27 30  0  0  1  0            999 V2000
    4.9833    3.2091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1950    3.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902    2.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8019    3.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7738    2.0868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5621    1.8437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.2293    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2293   -0.6180    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5801   -1.6570    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0373   -2.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2787   -1.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6680    1.2466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -0.2055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5940   -1.4566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5704   -2.3772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4017   -1.7310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  6  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
 10 12  1  1  0  0  0
 13 10  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  1  6  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 18 24  1  1  0  0  0
 17 25  1  1  0  0  0
 16 26  1  0  0  0  0
 14 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0044148

> <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=C(C)[C@]2(O)[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O7/c1-5-9(2)17(22)26-13-7-19(8-25-19)15-12(21)6-10(3)20(15,24)16-14(13)11(4)18(23)27-16/h5-6,12-16,21,24H,4,7-8H2,1-3H3/b9-5-/t12-,13-,14-,15+,16+,19+,20-/m1/s1

> <INCHI_KEY>
ADBOAFOIAMBXJT-WBNZXOOCSA-N

> <FORMULA>
C20H24O7

> <MOLECULAR_WEIGHT>
376.405

> <EXACT_MASS>
376.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.5607399174137

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4R,6R,6aR,7R,9aS,9bS)-7,9a-dihydroxy-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.03

> <JCHEM_LOGP>
1.1059214033333344

> <ALOGPS_LOGS>
-2.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.485355821587245

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.860437467545342

> <JCHEM_PKA_STRONGEST_BASIC>
-3.080290887710772

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
94.69199999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.93e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
euparotin

> <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  C   UNK     0       9.302   5.990   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.831   6.444   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.702   5.397   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.230   5.851   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.044   3.895   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.516   3.442   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       5.916   2.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.761   0.386   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.761  -1.154   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.549  -3.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.536  -4.253   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.120  -3.648   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.114   2.327   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.144  -0.384   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.590  -1.629   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.842  -2.719   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.798  -4.437   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.083  -3.231   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10   12                                                       
CONECT   12   11   10                                                       
CONECT   13   10   14   17                                                  
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   26                                                  
CONECT   17   16   13   18   25                                             
CONECT   18   17   19   24                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   18                                                       
CONECT   25   17                                                            
CONECT   26   16                                                            
CONECT   27   14                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₇

Average Mass

376.4050 Da

Monoisotopic Mass

376.15220 Da

IUPAC Name

(3aR,4R,6R,6aR,7R,9aS,9bS)-7,9a-dihydroxy-9-methyl-3-methylidene-2-oxo-3,3a,4,5,6a,7,9a,9b-octahydro-2H-spiro[azuleno[4,5-b]furan-6,2'-oxirane]-4-yl (2Z)-2-methylbut-2-enoate

Traditional Name

euparotin

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=C(C)[C@]2(O)[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C20H24O7/c1-5-9(2)17(22)26-13-7-19(8-25-19)15-12(21)6-10(3)20(15,24)16-14(13)11(4)18(23)27-16/h5-6,12-16,21,24H,4,7-8H2,1-3H3/b9-5-/t12-,13-,14-,15+,16+,19+,20-/m1/s1

InChI Key

ADBOAFOIAMBXJT-WBNZXOOCSA-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

Species Name	Source	Reference
Centaurea aggregata	Plant	KNApSAcK
Eupatorium rotundifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpene lactone (CHEBI:4929 )
Guaianolide (C09434 )

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	1.03	ALOGPS
logP	1.11	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	12.86	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	94.69 m³·mol⁻¹	ChemAxon
Polarizability	37.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003272

Chemspider ID

4444798

KEGG Compound ID

C09434

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281455

PDB ID

Not Available

ChEBI ID

4929

Good Scents ID

Not Available

References

General References

Hanson RL, Lardy HA, Kupchan SM: Inhibition of phosphofructokinase by quinone methide and alpha-methylene lactone tumor inhibitors. Science. 1970 Apr 17;168(3929):378-80. doi: 10.1126/science.168.3929.378. [PubMed:4244949 ]
Kupchan SM, Hemingway JC, Cassady JM, Knox JR, McPhail AT, Sim GA: The isolation and structural elucidation of euparotin acetate, a novel guaianolide tumor inhibitor from Eupatorium rotundifolium. J Am Chem Soc. 1967 Jan 18;89(2):465-6. doi: 10.1021/ja00978a061. [PubMed:6031638 ]
Werner Herz, Palianappan Kulanthaivel (1982). Sesquiterpene lactones of Eupatorium scabridum. Phytochemistry, Volume 21, Issue 10, 1982, Pages 2475-2479. DOI: 10.1016/0031-9422(82)85244-8. Phytochemistry.

Showing NP-Card for Euparotin (NP0044148)

MOL for NP0044148 (Euparotin)

3D MOL for NP0044148 (Euparotin)

3D SDF for NP0044148 (Euparotin)

3D-SDF for NP0044148 (Euparotin)

PDB for NP0044148 (Euparotin)

3D PDB for NP0044148 (Euparotin)

SMILES for NP0044148 (Euparotin)

INCHI for NP0044148 (Euparotin)

Structure for NP0044148 (Euparotin)

3D Structure for NP0044148 (Euparotin)