NP-MRD: Showing NP-Card for deacetylvitexilactone (NP0032199)

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Record Information

Version

2.0

Created at

2021-06-19 23:04:03 UTC

Updated at

2021-06-30 00:01:14 UTC

NP-MRD ID

NP0032199

Secondary Accession Numbers

None

Natural Product Identification

Common Name

deacetylvitexilactone

Provided By

JEOL Database JEOL Logo

Description

Deacetylvitexilactone belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. deacetylvitexilactone is found in Marrubium globosum, Marrubium globosum ssp. libanoticum and Marrubium globosum ssp.libanoticum. deacetylvitexilactone was first documented in 2006 (Rigano, D., et al.). Based on a literature review very few articles have been published on Deacetylvitexilactone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101043D          

 56 58  0  0  0  0            999 V2000
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    0.0285    1.6940    2.0926 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.4541    0.8806    1.8713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2523   -0.2959    2.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2367    0.6189    0.3638 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3920   -0.2028   -0.3429 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7107    0.6204   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -1.5709    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -0.3905   -1.8437 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.7361    0.2015    0.0456 C   0  0  1  0  0  0  0  0  0  0  0  0
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  7  8  1  6  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202101043D          

 56 58  0  0  0  0            999 V2000
   -0.7711    2.9076    2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    1.6940    2.0926 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5176    1.9755    2.3776 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4541    0.8806    1.8713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2523   -0.2959    2.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2367    0.6189    0.3638 C   0  0  1  0  0  0  0  0  0  0  0  0
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    5.1110    0.6847    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595   -1.4944    1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530   -2.3181    0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6284   -1.9932   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.5706   -2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7810   -1.0709   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -0.9740   -3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314   -1.9218   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810   -0.3398   -1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    1.0061   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -1.0667    1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0977   -1.9097    0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -1.5712    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    2.5547   -1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2196    2.1801    0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8701    0.8653   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4930    0.5823    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2059   -0.7617    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4036    1.5001   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879   -0.3269    2.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -1.7054    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  6  1  0  0  0  0
 20 19  2  0  0  0  0
 19 18  1  0  0  0  0
 18 17  1  0  0  0  0
 11 10  1  0  0  0  0
 15 16  1  6  0  0  0
 13 15  1  0  0  0  0
  6  4  1  0  0  0  0
  4  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2 15  1  0  0  0  0
  4  5  1  0  0  0  0
 19 24  1  0  0  0  0
  7  8  1  6  0  0  0
 24 23  1  0  0  0  0
  2  1  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  1  0  0  0
 15 17  1  0  0  0  0
 10  7  1  0  0  0  0
 23 21  1  0  0  0  0
 20 21  1  0  0  0  0
  6  7  1  0  0  0  0
 21 22  2  0  0  0  0
 13 12  1  0  0  0  0
  7  9  1  0  0  0  0
 24 55  1  0  0  0  0
 24 56  1  0  0  0  0
 20 54  1  0  0  0  0
 16 49  1  0  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 17 50  1  0  0  0  0
 17 51  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
 10 40  1  0  0  0  0
 10 41  1  0  0  0  0
 12 44  1  0  0  0  0
 12 45  1  0  0  0  0
  6 33  1  6  0  0  0
  4 31  1  6  0  0  0
  3 29  1  0  0  0  0
  3 30  1  0  0  0  0
  2 28  1  1  0  0  0
  5 32  1  0  0  0  0
  8 34  1  0  0  0  0
  8 35  1  0  0  0  0
  8 36  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 14 48  1  0  0  0  0
  9 37  1  0  0  0  0
  9 38  1  0  0  0  0
  9 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0032199

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@](O[H])(C([H])([H])C([H])([H])C2=C([H])C(=O)OC2([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]12[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-13-10-15(21)17-18(2,3)7-5-8-19(17,4)20(13,23)9-6-14-11-16(22)24-12-14/h11,13,15,17,21,23H,5-10,12H2,1-4H3/t13-,15-,17+,19+,20-/m1/s1

> <INCHI_KEY>
DCNLUKIGAMIKOK-YJLWDSPXSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.472

> <EXACT_MASS>
336.23005951

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.15645577346982

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2-[(1R,2R,4R,4aS,8aS)-1,4-dihydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl]ethyl}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
3.0541532646666663

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.101249602883893

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.443359024460477

> <JCHEM_PKA_STRONGEST_BASIC>
-2.843081481029113

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
93.46979999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{2-[(1R,2R,4R,4aS,8aS)-1,4-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-2H-naphthalen-1-yl]ethyl}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
   -0.7711    2.9076    2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    1.6940    2.0926 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5176    1.9755    2.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541    0.8806    1.8713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2523   -0.2959    2.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2367    0.6189    0.3638 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3920   -0.2028   -0.3429 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7107    0.6204   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -1.5709    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -0.3905   -1.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -0.9065   -2.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118    0.0368   -1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    0.2015    0.0456 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3285   -1.1479    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    1.3724    0.5804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1432    2.5836   -0.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    1.1840    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815    0.2608    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451    0.2016    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7342    0.8176   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1289    0.4013    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0377    0.7738   -0.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2379   -0.4591    1.0704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9520   -0.6458    1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5156    3.8208    2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5565    3.0867    3.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501    2.7562    2.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690    0.8341    2.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097    2.9315    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513    2.0878    3.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    1.2112    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075   -0.0895    3.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    1.6124   -0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    1.6409   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4887    0.1595   -0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    0.6847    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595   -1.4944    1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530   -2.3181    0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6284   -1.9932   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.5706   -2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7810   -1.0709   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -0.9740   -3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314   -1.9218   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810   -0.3398   -1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    1.0061   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -1.0667    1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0977   -1.9097    0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -1.5712    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    2.5547   -1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2196    2.1801    0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8701    0.8653   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4930    0.5823    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2059   -0.7617    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4036    1.5001   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879   -0.3269    2.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -1.7054    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  6  1  0
 20 19  2  0
 19 18  1  0
 18 17  1  0
 11 10  1  0
 15 16  1  6
 13 15  1  0
  6  4  1  0
  4  3  1  0
  3  2  1  0
  2 15  1  0
  4  5  1  0
 19 24  1  0
  7  8  1  6
 24 23  1  0
  2  1  1  0
 11 12  1  0
 13 14  1  1
 15 17  1  0
 10  7  1  0
 23 21  1  0
 20 21  1  0
  6  7  1  0
 21 22  2  0
 13 12  1  0
  7  9  1  0
 24 55  1  0
 24 56  1  0
 20 54  1  0
 16 49  1  0
 18 52  1  0
 18 53  1  0
 17 50  1  0
 17 51  1  0
 11 42  1  0
 11 43  1  0
 10 40  1  0
 10 41  1  0
 12 44  1  0
 12 45  1  0
  6 33  1  6
  4 31  1  6
  3 29  1  0
  3 30  1  0
  2 28  1  1
  5 32  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0      -0.771   2.908   2.605  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.029   1.694   2.093  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.518   1.976   2.378  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.454   0.881   1.871  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.252  -0.296   2.644  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.237   0.619   0.364  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.392  -0.203  -0.343  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.711   0.620  -0.288  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.733  -1.571   0.279  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.059  -0.391  -1.844  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.651  -0.907  -2.098  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.612   0.037  -1.500  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.736   0.202   0.046  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.329  -1.148   0.681  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.231   1.372   0.580  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.143   2.584  -0.125  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.753   1.184   0.266  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.582   0.261   1.174  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.045   0.202   0.847  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.734   0.818  -0.113  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.129   0.401   0.024  0.00  0.00           C+0
HETATM   22  O   UNK     0      -7.038   0.774  -0.694  0.00  0.00           O+0
HETATM   23  O   UNK     0      -6.238  -0.459   1.070  0.00  0.00           O+0
HETATM   24  C   UNK     0      -4.952  -0.646   1.658  0.00  0.00           C+0
HETATM   25  H   UNK     0      -0.516   3.821   2.057  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.557   3.087   3.664  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.850   2.756   2.521  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.269   0.834   2.703  0.00  0.00           H+0
HETATM   29  H   UNK     0       1.810   2.932   1.924  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.651   2.088   3.462  0.00  0.00           H+0
HETATM   31  H   UNK     0       3.481   1.211   2.055  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.507  -0.090   3.560  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.344   1.612  -0.101  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.563   1.641  -0.658  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.489   0.160  -0.908  0.00  0.00           H+0
HETATM   36  H   UNK     0       5.111   0.685   0.729  0.00  0.00           H+0
HETATM   37  H   UNK     0       3.959  -1.494   1.345  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.953  -2.318   0.140  0.00  0.00           H+0
HETATM   39  H   UNK     0       4.628  -1.993  -0.195  0.00  0.00           H+0
HETATM   40  H   UNK     0       3.168   0.571  -2.365  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.781  -1.071  -2.313  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.488  -0.974  -3.181  0.00  0.00           H+0
HETATM   43  H   UNK     0       1.531  -1.922  -1.707  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.381  -0.340  -1.771  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.719   1.006  -2.001  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.080  -1.067   1.741  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.098  -1.910   0.601  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.545  -1.571   0.174  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.237   2.555  -1.019  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.220   2.180   0.283  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.870   0.865  -0.776  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.493   0.582   2.216  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.206  -0.762   1.128  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.404   1.500  -0.875  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.988  -0.327   2.704  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.685  -1.705   1.603  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3   15    1   28                                             
CONECT    3    4    2   29   30                                             
CONECT    4    6    3    5   31                                             
CONECT    5    4   32                                                       
CONECT    6   13    4    7   33                                             
CONECT    7    8   10    6    9                                             
CONECT    8    7   34   35   36                                             
CONECT    9    7   37   38   39                                             
CONECT   10   11    7   40   41                                             
CONECT   11   10   12   42   43                                             
CONECT   12   11   13   44   45                                             
CONECT   13    6   15   14   12                                             
CONECT   14   13   46   47   48                                             
CONECT   15   16   13    2   17                                             
CONECT   16   15   49                                                       
CONECT   17   18   15   50   51                                             
CONECT   18   19   17   52   53                                             
CONECT   19   20   18   24                                                  
CONECT   20   19   21   54                                                  
CONECT   21   23   20   22                                                  
CONECT   22   21                                                            
CONECT   23   24   21                                                       
CONECT   24   19   23   55   56                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    3                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    6                                                            
CONECT   34    8                                                            
CONECT   35    8                                                            
CONECT   36    8                                                            
CONECT   37    9                                                            
CONECT   38    9                                                            
CONECT   39    9                                                            
CONECT   40   10                                                            
CONECT   41   10                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   12                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   14                                                            
CONECT   49   16                                                            
CONECT   50   17                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   20                                                            
CONECT   55   24                                                            
CONECT   56   24                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
   -0.7711    2.9076    2.6048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0285    1.6940    2.0926 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5176    1.9755    2.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4541    0.8806    1.8713 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2523   -0.2959    2.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2367    0.6189    0.3638 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3920   -0.2028   -0.3429 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7107    0.6204   -0.2876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7328   -1.5709    0.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -0.3905   -1.8437 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513   -0.9065   -2.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6118    0.0368   -1.5005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7361    0.2015    0.0456 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3285   -1.1479    0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2312    1.3724    0.5804 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1432    2.5836   -0.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7527    1.1840    0.2659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5815    0.2608    1.1740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0451    0.2016    0.8470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7342    0.8176   -0.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1289    0.4013    0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0377    0.7738   -0.6944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2379   -0.4591    1.0704 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9520   -0.6458    1.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5156    3.8208    2.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5565    3.0867    3.6644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501    2.7562    2.5214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2690    0.8341    2.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8097    2.9315    1.9240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6513    2.0878    3.4616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4805    1.2112    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5075   -0.0895    3.5601 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3436    1.6124   -0.1012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5625    1.6409   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4887    0.1595   -0.9083 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1110    0.6847    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9595   -1.4944    1.3454 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9530   -2.3181    0.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6284   -1.9932   -0.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1681    0.5706   -2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7810   -1.0709   -2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -0.9740   -3.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5314   -1.9218   -1.7070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3810   -0.3398   -1.7710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7188    1.0061   -2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0804   -1.0667    1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0977   -1.9097    0.6010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5447   -1.5712    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2373    2.5547   -1.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2196    2.1801    0.2834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8701    0.8653   -0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4930    0.5823    2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2059   -0.7617    1.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4036    1.5001   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9879   -0.3269    2.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6848   -1.7054    1.6031 H   0  0  0  0  0  0  0  0  0  0  0  0
 13  6  1  0
 20 19  2  0
 19 18  1  0
 18 17  1  0
 11 10  1  0
 15 16  1  6
 13 15  1  0
  6  4  1  0
  4  3  1  0
  3  2  1  0
  2 15  1  0
  4  5  1  0
 19 24  1  0
  7  8  1  6
 24 23  1  0
  2  1  1  0
 11 12  1  0
 13 14  1  1
 15 17  1  0
 10  7  1  0
 23 21  1  0
 20 21  1  0
  6  7  1  0
 21 22  2  0
 13 12  1  0
  7  9  1  0
 24 55  1  0
 24 56  1  0
 20 54  1  0
 16 49  1  0
 18 52  1  0
 18 53  1  0
 17 50  1  0
 17 51  1  0
 11 42  1  0
 11 43  1  0
 10 40  1  0
 10 41  1  0
 12 44  1  0
 12 45  1  0
  6 33  1  6
  4 31  1  6
  3 29  1  0
  3 30  1  0
  2 28  1  1
  5 32  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
 14 46  1  0
 14 47  1  0
 14 48  1  0
  9 37  1  0
  9 38  1  0
  9 39  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4720 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

4-{2-[(1R,2R,4R,4aS,8aS)-1,4-dihydroxy-2,5,5,8a-tetramethyl-decahydronaphthalen-1-yl]ethyl}-2,5-dihydrofuran-2-one

Traditional Name

4-{2-[(1R,2R,4R,4aS,8aS)-1,4-dihydroxy-2,5,5,8a-tetramethyl-hexahydro-2H-naphthalen-1-yl]ethyl}-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@](O[H])(C([H])([H])C([H])([H])C2=C([H])C(=O)OC2([H])[H])[C@@]2(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]12[H]

InChI Identifier

InChI=1S/C20H32O4/c1-13-10-15(21)17-18(2,3)7-5-8-19(17,4)20(13,23)9-6-14-11-16(22)24-12-14/h11,13,15,17,21,23H,5-10,12H2,1-4H3/t13-,15-,17+,19+,20-/m1/s1

InChI Key

DCNLUKIGAMIKOK-YJLWDSPXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, 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
Marrubium globosum	LOTUS Database	35616633
Marrubium globosum ssp. libanoticum	JEOL database	Rigano, D., et al, J. Nat. Prod. 69, 836 (2006)
Marrubium globosum ssp.libanoticum	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Clerodane diterpenoid
Diterpenoid
Abscisic acid
2-furanone
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Secondary alcohol
Lactone
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	2.58	ALOGPS
logP	3.05	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.44	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	93.47 m³·mol⁻¹	ChemAxon
Polarizability	38.16 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

24677519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46883141

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rigano, D., et al. (2006). Rigano, D., et al, J. Nat. Prod. 69, 836 (2006) . J. Nat. Prod..

Showing NP-Card for deacetylvitexilactone (NP0032199)

MOL for NP0032199 (deacetylvitexilactone)

3D MOL for NP0032199 (deacetylvitexilactone)

3D SDF for NP0032199 (deacetylvitexilactone)

3D-SDF for NP0032199 (deacetylvitexilactone)

PDB for NP0032199 (deacetylvitexilactone)

3D PDB for NP0032199 (deacetylvitexilactone)

SMILES for NP0032199 (deacetylvitexilactone)

INCHI for NP0032199 (deacetylvitexilactone)

Structure for NP0032199 (deacetylvitexilactone)

3D Structure for NP0032199 (deacetylvitexilactone)