NP-MRD: Showing NP-Card for (2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate (NP0231386)

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Record Information

Version

2.0

Created at

2022-09-06 12:13:37 UTC

Updated at

2022-09-06 12:13:37 UTC

NP-MRD ID

NP0231386

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate

Description

GOYAZENSOLIDE belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. (2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate is found in Koyamasia calcarea and Lychnophora ericoides. (2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate was first documented in 2020 (PMID: 32630308). Based on a literature review a small amount of articles have been published on GOYAZENSOLIDE (PMID: 33359866) (PMID: 35772286) (PMID: 35512655) (PMID: 34235256).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062214132D          

 26 28  0  0  1  0            999 V2000
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9060    4.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  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
 26 24  1  1  0  0  0
  7 26  1  0  0  0  0
 20 26  1  0  0  0  0
M  END

     RDKit          3D

 46 48  0  0  0  0  0  0  0  0999 V2000
    3.1450   -1.9168    0.8092 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -0.8721    0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0219   -0.6848   -0.1146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6367    0.1340   -0.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0528    1.1310   -1.0236 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2701    0.0130   -0.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3274    0.9624   -0.6610 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5795    0.3951   -1.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5009   -1.1349   -1.5996 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7290   -1.6533   -2.2898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -1.4151   -0.2242 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8461   -1.4219    0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5017   -2.0394   -0.8606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7354   -1.7954   -2.0769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0725   -2.0895   -3.2434 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3925   -0.8696    1.3761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4477   -1.6210    2.1511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8151   -0.9098    3.2890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9405    0.2974    1.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6543    1.4078    0.8540 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9728    2.5946    1.6227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3750    3.6763    0.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8024    4.8539    0.8793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1495    3.1235    0.3815 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057    3.8784   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2505    1.6492    0.5158 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8298   -2.6418    1.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -2.0474    0.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1751   -0.6057   -1.2183 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3439    0.2899    0.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6243   -1.4901    0.3064 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9613    1.7300   -1.2035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6261    0.6532   -1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408    0.6135   -2.7404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3652   -2.1752   -1.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4515   -2.4130   -3.0491 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090   -0.8335   -2.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4365   -2.6093   -0.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0724   -2.6009    2.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3663   -1.7527    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0423   -1.5445    4.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7952    0.3919    2.8873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3817    1.4757    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7131    3.4838   -0.5596 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7369    4.9663   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3482    1.4167    1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  6
  9 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 12 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  2  3
 24 26  1  0
 26  7  1  0
 14  9  1  0
 26 20  1  0
  3 29  1  0
  3 30  1  0
  3 31  1  0
  1 27  1  0
  1 28  1  0
  7 32  1  6
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 13 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  6
 25 44  1  0
 25 45  1  0
 26 46  1  1
M  END


  Mrv1652309062214132D          

 26 28  0  0  1  0            999 V2000
    0.5371   -2.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2015   -1.6761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -1.5898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865   -1.0086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5069   -1.0949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6204    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8900   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4051    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.9049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6746    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    2.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6204    3.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9060    4.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8358    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.9049    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4337    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9187    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7437    1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6887    0.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  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
 26 24  1  1  0  0  0
  7 26  1  0  0  0  0
 20 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0231386

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O7/c1-9(2)17(22)25-14-7-19(4)15(21)6-12(26-19)11(8-20)5-13-16(14)10(3)18(23)24-13/h5-6,13-14,16,20H,1,3,7-8H2,2,4H3/b11-5-/t13-,14+,16+,19-/m1/s1

> <INCHI_KEY>
HTMCLLSRQWRPTN-OKMRAYSCSA-N

> <FORMULA>
C19H20O7

> <MOLECULAR_WEIGHT>
360.362

> <EXACT_MASS>
360.120902984

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.22073132209398

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,4R,8R,9S,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate

> <JCHEM_LOGP>
1.4031655976666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.021146287600608

> <JCHEM_PKA_STRONGEST_BASIC>
-2.789550613803476

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
92.32830000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,4R,8R,9S,11R)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       1.003  -4.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.376  -3.129   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.155  -2.968   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.281  -1.883   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.813  -2.044   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.560   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.025   0.294   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.489   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.395  -0.476   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.985   2.786   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.489   4.802   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.395   3.556   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.395   2.016   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.859   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.025   5.278   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.025   6.818   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.691   7.588   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.560   4.802   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.655   3.556   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.810   4.032   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.715   2.786   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.255   2.786   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.810   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.286   0.075   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   26                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11   14                                             
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    7   20                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
Furanoheliangolide	MeSH

Chemical Formula

C₁₉H₂₀O₇

Average Mass

360.3620 Da

Monoisotopic Mass

360.12090 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=C)C(=O)O[C@H]1C[C@@]2(C)OC(=CC2=O)\C(CO)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C19H20O7/c1-9(2)17(22)25-14-7-19(4)15(21)6-12(26-19)11(8-20)5-13-16(14)10(3)18(23)24-13/h5-6,13-14,16,20H,1,3,7-8H2,2,4H3/b11-5-/t13-,14+,16+,19-/m1/s1

InChI Key

HTMCLLSRQWRPTN-OKMRAYSCSA-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
Koyamasia calcarea	LOTUS Database	35616633
Lychnophora ericoides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Sesquiterpenoid
Dicarboxylic acid or derivatives
3-furanone
Gamma butyrolactone
Dihydrofuran
Oxolane
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003293

Chemspider ID

4513541

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5358393

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bernardes ACFPF, Matosinhos RC, de Paula Michel Araujo MC, Barros CH, de Oliveira Aguiar Soares RD, Costa DC, Sachs D, Saude-Guimaraes DA: Sesquiterpene lactones from Lychnophora species: Antinociceptive, anti-inflammatory, and antioxidant pathways to treat acute gout. J Ethnopharmacol. 2021 Apr 6;269:113738. doi: 10.1016/j.jep.2020.113738. Epub 2020 Dec 24. [PubMed:33359866 ]
Patouret R, Barluenga S, Winssinger N: Withaferin A, a polyfunctional pharmacophore that includes covalent engagement of IPO5, is an inhibitor of influenza A replication. Bioorg Med Chem. 2022 Sep 1;69:116883. doi: 10.1016/j.bmc.2022.116883. Epub 2022 Jun 18. [PubMed:35772286 ]
Tana IDT, Saude-Guimaraes DA, Caldeira TG, de Freitas Marques MB, Mussel WDN, de Souza J: Biopharmaceutics studies applied to goyazensolide: a drug candidate from Lychnophora species. J Pharm Pharmacol. 2022 Aug 19;74(8):1140-1151. doi: 10.1093/jpp/rgac020. [PubMed:35512655 ]
Liu W, Patouret R, Barluenga S, Plank M, Loewith R, Winssinger N: Identification of a Covalent Importin-5 Inhibitor, Goyazensolide, from a Collective Synthesis of Furanoheliangolides. ACS Cent Sci. 2021 Jun 23;7(6):954-962. doi: 10.1021/acscentsci.1c00056. Epub 2021 May 25. [PubMed:34235256 ]
Izumi C, Laure HJ, Barbosa NG, Thome CH, Ferreira GA, Sousa JPB, Lopes NP, Rosa JC: Sequesterpene Lactones Isolated from a Brazilian Cerrado Plant (Eremanthus spp.) as Anti-Proliferative Compounds, Characterized by Functional and Proteomic Analysis, are Candidates for New Therapeutics in Glioblastoma. Int J Mol Sci. 2020 Jul 1;21(13):4713. doi: 10.3390/ijms21134713. [PubMed:32630308 ]
LOTUS database [Link]

Showing NP-Card for (2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate (NP0231386)

MOL for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D MOL for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D SDF for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D-SDF for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

PDB for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D PDB for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

SMILES for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

INCHI for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

Structure for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)

3D Structure for NP0231386 ((2z,4r,8r,9s,11r)-2-(hydroxymethyl)-11-methyl-7-methylidene-6,12-dioxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-1(13),2-dien-9-yl 2-methylprop-2-enoate)