NP-MRD: Showing NP-Card for culcitiolide F (NP0042799)

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Record Information

Version

2.0

Created at

2021-06-21 00:22:35 UTC

Updated at

2021-06-30 00:18:06 UTC

NP-MRD ID

NP0042799

Secondary Accession Numbers

None

Natural Product Identification

Common Name

culcitiolide F

Provided By

JEOL Database JEOL Logo

Description

Culcitiolide F belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. culcitiolide F is found in Senecio culcitioides. culcitiolide F was first documented in 2013 (Mitsui, T., et al.). Based on a literature review very few articles have been published on Culcitiolide F.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102223D          

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     RDKit          3D

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    1.7470   -0.4041   -4.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -1.1098   -3.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010   -0.0346    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949   -1.1069   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4136    0.4191   -1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -1.1249   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098   -0.6641    3.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -4.2308    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -4.2838    4.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693   -4.8195    3.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -2.8545    6.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060   -1.5462    5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8437   -3.2225    5.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5868   -1.3189   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1303   -1.6765   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3849   -0.6462   -1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  3  1  0  0  0  0
  8  6  1  0  0  0  0
 25 26  2  0  0  0  0
  9 10  1  0  0  0  0
 23 24  1  0  0  0  0
  5  4  1  0  0  0  0
  6  7  2  0  0  0  0
 12 14  1  0  0  0  0
  5 33  1  1  0  0  0
 14 22  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
 10 11  1  0  0  0  0
  3 22  1  0  0  0  0
 12 13  1  6  0  0  0
 10 12  1  0  0  0  0
 14 15  1  0  0  0  0
  5  6  1  0  0  0  0
 15 16  1  0  0  0  0
  5 12  1  0  0  0  0
 16 18  1  0  0  0  0
 16 17  2  0  0  0  0
  8  9  1  0  0  0  0
 18 19  2  3  0  0  0
 22 23  2  0  0  0  0
 19 20  1  0  0  0  0
 23 25  1  0  0  0  0
 19 21  1  0  0  0  0
 25 27  1  0  0  0  0
  2  1  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 10 38  1  1  0  0  0
 14 45  1  6  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
 24 53  1  0  0  0  0
 24 54  1  0  0  0  0
 24 55  1  0  0  0  0
 11 39  1  0  0  0  0
 11 40  1  0  0  0  0
 11 41  1  0  0  0  0
 13 42  1  0  0  0  0
 13 43  1  0  0  0  0
 13 44  1  0  0  0  0
 18 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 20 49  1  0  0  0  0
 21 50  1  0  0  0  0
 21 51  1  0  0  0  0
 21 52  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0042799

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(C(=O)O[C@]1([H])C2=C(C(=O)O[C@@]2(OC([H])([H])[H])C([H])([H])[C@@]2([H])C(=O)C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H28O6/c1-11(2)9-16(23)26-18-17-13(4)19(24)27-21(17,25-6)10-14-15(22)8-7-12(3)20(14,18)5/h9,12,14,18H,7-8,10H2,1-6H3/t12-,14-,18+,20+,21-/m0/s1

> <INCHI_KEY>
UDAQXTOMMRTMKH-QIGGNRJRSA-N

> <FORMULA>
C21H28O6

> <MOLECULAR_WEIGHT>
376.449

> <EXACT_MASS>
376.188588622

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.04784825682705

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,5S,8aR,9aS)-9a-methoxy-3,4a,5-trimethyl-2,8-dioxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate

> <ALOGPS_LOGP>
2.81

> <JCHEM_LOGP>
3.969318230666667

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.586160654857185

> <JCHEM_PKA_STRONGEST_BASIC>
-4.339317496557845

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
99.26119999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.81e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,4aR,5S,8aR,9aS)-9a-methoxy-3,4a,5-trimethyl-2,8-dioxo-4H,5H,6H,7H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 57  0  0  0  0  0  0  0  0999 V2000
    2.5353    2.9906    2.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735    1.8324    2.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8414    1.9683    0.7256 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8999    2.8024   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545    2.0862   -0.3914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2950    2.9705   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024    3.6602   -0.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    3.0593   -2.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085    1.6821   -3.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180    0.7733   -2.4943 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3811   -0.5685   -3.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077    0.6517   -1.0050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6755   -0.0552   -0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094   -0.1767   -0.1157 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0884   -0.4569    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265   -1.5676    1.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3445   -2.3683    1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328   -1.6169    3.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -2.6914    3.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300   -4.0739    3.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0333   -2.5680    5.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9562    0.6098    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263    0.3081   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8611   -0.8966   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0051    1.4976    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2114    1.6104    0.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1687    2.4772    0.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524    2.7610    3.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640    3.8347    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914    3.2581    2.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069    3.7781    0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975    3.0449   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    2.0064    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    3.5795   -3.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9995    3.6668   -2.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.8072   -4.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6631    1.1998   -3.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2127    1.2371   -2.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109   -1.2157   -2.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7470   -0.4041   -4.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -1.1098   -3.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010   -0.0346    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949   -1.1069   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4136    0.4191   -1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -1.1249   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098   -0.6641    3.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -4.2308    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -4.2838    4.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693   -4.8195    3.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -2.8545    6.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060   -1.5462    5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8437   -3.2225    5.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5868   -1.3189   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1303   -1.6765   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3849   -0.6462   -1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  3  1  0
  8  6  1  0
 25 26  2  0
  9 10  1  0
 23 24  1  0
  5  4  1  0
  6  7  2  0
 12 14  1  0
  5 33  1  1
 14 22  1  0
  3  2  1  1
  3  4  1  0
 10 11  1  0
  3 22  1  0
 12 13  1  6
 10 12  1  0
 14 15  1  0
  5  6  1  0
 15 16  1  0
  5 12  1  0
 16 18  1  0
 16 17  2  0
  8  9  1  0
 18 19  2  3
 22 23  2  0
 19 20  1  0
 23 25  1  0
 19 21  1  0
 25 27  1  0
  2  1  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 14 45  1  6
  4 31  1  0
  4 32  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       2.535   2.991   2.870  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.373   1.832   2.064  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.841   1.968   0.726  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.900   2.802  -0.144  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.555   2.086  -0.391  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.295   2.970  -1.288  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.202   3.660  -0.824  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.093   3.059  -2.744  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.309   1.682  -3.349  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.218   0.773  -2.494  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.381  -0.569  -3.224  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.708   0.652  -1.005  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.676  -0.055  -0.956  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.709  -0.177  -0.116  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.088  -0.457   1.153  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.527  -1.568   1.799  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.345  -2.368   1.382  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.833  -1.617   3.108  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.722  -2.691   3.913  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.230  -4.074   3.608  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.033  -2.568   5.247  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.956   0.610   0.139  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.226   0.308  -0.132  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.861  -0.897  -0.709  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.005   1.498   0.231  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.211   1.610   0.111  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.169   2.477   0.666  0.00  0.00           O+0
HETATM   28  H   UNK     0       2.152   2.761   3.868  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.964   3.835   2.477  0.00  0.00           H+0
HETATM   30  H   UNK     0       3.591   3.258   2.967  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.707   3.778   0.317  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.397   3.045  -1.092  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.028   2.006   0.570  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.701   3.579  -3.291  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.000   3.667  -2.825  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.748   1.807  -4.347  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.663   1.200  -3.509  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.213   1.237  -2.486  0.00  0.00           H+0
HETATM   39  H   UNK     0       2.111  -1.216  -2.731  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.747  -0.404  -4.244  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.434  -1.110  -3.302  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.101  -0.035   0.054  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.595  -1.107  -1.250  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.414   0.419  -1.608  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.923  -1.125  -0.617  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.410  -0.664   3.415  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.464  -4.231   2.553  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.127  -4.284   4.199  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.469  -4.819   3.865  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.717  -2.854   6.053  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.306  -1.546   5.448  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.844  -3.223   5.285  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.587  -1.319  -0.006  0.00  0.00           H+0
HETATM   54  H   UNK     0       4.130  -1.677  -0.940  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.385  -0.646  -1.637  0.00  0.00           H+0
CONECT    1    2   28   29   30                                             
CONECT    2    3    1                                                       
CONECT    3   27    2    4   22                                             
CONECT    4    5    3   31   32                                             
CONECT    5    4   33    6   12                                             
CONECT    6    8    7    5                                                  
CONECT    7    6                                                            
CONECT    8    6    9   34   35                                             
CONECT    9   10    8   36   37                                             
CONECT   10    9   11   12   38                                             
CONECT   11   10   39   40   41                                             
CONECT   12   14   13   10    5                                             
CONECT   13   12   42   43   44                                             
CONECT   14   12   22   15   45                                             
CONECT   15   14   16                                                       
CONECT   16   15   18   17                                                  
CONECT   17   16                                                            
CONECT   18   16   19   46                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   47   48   49                                             
CONECT   21   19   50   51   52                                             
CONECT   22   14    3   23                                                  
CONECT   23   24   22   25                                                  
CONECT   24   23   53   54   55                                             
CONECT   25   26   23   27                                                  
CONECT   26   25                                                            
CONECT   27    3   25                                                       
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   11                                                            
CONECT   41   11                                                            
CONECT   42   13                                                            
CONECT   43   13                                                            
CONECT   44   13                                                            
CONECT   45   14                                                            
CONECT   46   18                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   20                                                            
CONECT   50   21                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   24                                                            
CONECT   54   24                                                            
CONECT   55   24                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

RDKit          3D

55 57  0  0  0  0  0  0  0  0999 V2000
    2.5353    2.9906    2.8696 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3735    1.8324    2.0637 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8414    1.9683    0.7256 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8999    2.8024   -0.1442 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545    2.0862   -0.3914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2950    2.9705   -1.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2024    3.6602   -0.8239 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0925    3.0593   -2.7441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3085    1.6821   -3.3485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2180    0.7733   -2.4943 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3811   -0.5685   -3.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7077    0.6517   -1.0050 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6755   -0.0552   -0.9556 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7094   -0.1767   -0.1157 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0884   -0.4569    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5265   -1.5676    1.7988 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3445   -2.3683    1.3819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8328   -1.6169    3.1076 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7215   -2.6914    3.9129 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2300   -4.0739    3.6079 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0333   -2.5680    5.2473 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9562    0.6098    0.1387 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263    0.3081   -0.1316 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8611   -0.8966   -0.7086 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0051    1.4976    0.2309 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2114    1.6104    0.1107 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1687    2.4772    0.6661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1524    2.7610    3.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640    3.8347    2.4766 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914    3.2581    2.9668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069    3.7781    0.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3975    3.0449   -1.0922 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0276    2.0064    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7013    3.5795   -3.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9995    3.6668   -2.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.8072   -4.3466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6631    1.1998   -3.5086 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2127    1.2371   -2.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1109   -1.2157   -2.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7470   -0.4041   -4.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -1.1098   -3.3021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010   -0.0346    0.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5949   -1.1069   -1.2495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4136    0.4191   -1.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -1.1249   -0.6166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4098   -0.6641    3.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4636   -4.2308    2.5533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1273   -4.2838    4.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693   -4.8195    3.8652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171   -2.8545    6.0531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3060   -1.5462    5.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8437   -3.2225    5.2849 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5868   -1.3189   -0.0063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1303   -1.6765   -0.9395 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3849   -0.6462   -1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
 27  3  1  0
  8  6  1  0
 25 26  2  0
  9 10  1  0
 23 24  1  0
  5  4  1  0
  6  7  2  0
 12 14  1  0
  5 33  1  1
 14 22  1  0
  3  2  1  1
  3  4  1  0
 10 11  1  0
  3 22  1  0
 12 13  1  6
 10 12  1  0
 14 15  1  0
  5  6  1  0
 15 16  1  0
  5 12  1  0
 16 18  1  0
 16 17  2  0
  8  9  1  0
 18 19  2  3
 22 23  2  0
 19 20  1  0
 23 25  1  0
 19 21  1  0
 25 27  1  0
  2  1  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  1
 14 45  1  6
  4 31  1  0
  4 32  1  0
 24 53  1  0
 24 54  1  0
 24 55  1  0
 11 39  1  0
 11 40  1  0
 11 41  1  0
 13 42  1  0
 13 43  1  0
 13 44  1  0
 18 46  1  0
 20 47  1  0
 20 48  1  0
 20 49  1  0
 21 50  1  0
 21 51  1  0
 21 52  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₈O₆

Average Mass

376.4490 Da

Monoisotopic Mass

376.18859 Da

IUPAC Name

(4S,4aR,5S,8aR,9aS)-9a-methoxy-3,4a,5-trimethyl-2,8-dioxo-2H,4H,4aH,5H,6H,7H,8H,8aH,9H,9aH-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate

Traditional Name

(4S,4aR,5S,8aR,9aS)-9a-methoxy-3,4a,5-trimethyl-2,8-dioxo-4H,5H,6H,7H,8aH,9H-naphtho[2,3-b]furan-4-yl 3-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]C(C(=O)O[C@]1([H])C2=C(C(=O)O[C@@]2(OC([H])([H])[H])C([H])([H])[C@@]2([H])C(=O)C([H])([H])C([H])([H])[C@]([H])(C([H])([H])[H])[C@@]12C([H])([H])[H])C([H])([H])[H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C21H28O6/c1-11(2)9-16(23)26-18-17-13(4)19(24)27-21(17,25-6)10-14-15(22)8-7-12(3)20(14,18)5/h9,12,14,18H,7-8,10H2,1-6H3/t12-,14-,18+,20+,21-/m0/s1

InChI Key

UDAQXTOMMRTMKH-QIGGNRJRSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Senecio culcitioides	JEOL database	Mitsui, T., et al., Chem. Pharm. Bull. 61, 816 (2013)

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
Eremophilanolide or secoeremophilanolide
Sesquiterpenoid
Naphthofuran
Ketal
Fatty acid ester
2-furanone
Dicarboxylic acid or derivatives
Fatty acyl
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aldehyde
Organooxygen compound
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
logP	2.81	ALOGPS
logP	3.97	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	16.59	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	99.26 m³·mol⁻¹	ChemAxon
Polarizability	40.05 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71763433

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mitsui, T., et al. (2013). Mitsui, T., et al., Chem. Pharm. Bull. 61, 816 (2013). Chem. Pharm. Bull..

Showing NP-Card for culcitiolide F (NP0042799)

MOL for NP0042799 (culcitiolide F)

3D MOL for NP0042799 (culcitiolide F)

3D SDF for NP0042799 (culcitiolide F)

3D-SDF for NP0042799 (culcitiolide F)

PDB for NP0042799 (culcitiolide F)

3D PDB for NP0042799 (culcitiolide F)

SMILES for NP0042799 (culcitiolide F)

INCHI for NP0042799 (culcitiolide F)

Structure for NP0042799 (culcitiolide F)

3D Structure for NP0042799 (culcitiolide F)