NP-MRD: Showing NP-Card for (7E,12E,20Z,18S)-Variabilin (NP0331317)

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Record Information

Version

1.0

Created at

2022-12-22 12:58:43 UTC

Updated at

2024-04-19 09:36:42 UTC

NP-MRD ID

NP0331317

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7E,12E,20Z,18S)-Variabilin

Description

7E,12E,20Z-variabilin belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. It was first documented in 2009 (PMID: 19413109). Based on a literature review very few articles have been published on 7E,12E,20Z-variabilin (PMID: 32074951).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052203292D          

 29 30  0  0  1  0            999 V2000
   -1.4133  -10.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -9.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -8.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679   -8.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5158   -8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5158   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986   -7.1741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1986   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9131   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3420   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4855   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6289   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0578   -5.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1440   -5.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9510   -4.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3635   -5.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115   -6.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516   -8.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -9.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816  -10.3486    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
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  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
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END

     RDKit          3D

 63 64  0  0  0  0  0  0  0  0999 V2000
    8.2181    3.2446    0.8339 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4799    1.9899    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2088    1.8683    0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3052    2.9217    0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8838    0.4422   -0.0110 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7243   -0.0807   -0.3612 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4751   -1.5297   -0.5434 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7008   -2.3485   -0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4007   -1.9398    0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1270   -1.1843    0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0380   -1.5964    1.1413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052   -0.8021    0.8212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2077    0.6724    0.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3261   -1.4317    0.4737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5326   -0.6061    0.1654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0021   -0.8479   -1.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1877   -0.0240   -1.5344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692    1.4584   -1.4218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3721   -0.5099   -1.8790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5646    0.3392   -2.1532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6442   -0.0657   -1.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1013    0.1765    0.2061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3948   -0.7034    0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1068   -0.0302    2.1715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6074    1.1825    2.0980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2109    1.3456    0.9366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0211   -0.2780    0.2338 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0137    0.6334    0.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2254    0.3854    0.8731 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5187    3.9724    1.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7298    3.6317   -0.0557 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0190    3.0719    1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7892    3.1671    0.8880 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9192    0.6204   -0.5242 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1512   -1.7707   -1.5734 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9645   -2.2525    0.8693 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3630   -3.4238   -0.3003 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5221   -2.2446   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1986   -3.0239    0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7214   -1.6588    1.4739 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2362   -0.0909    0.3010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8034   -1.4493   -0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8317   -2.6696    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3326   -1.3040    2.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7946    1.0025    1.2294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639    1.1297   -0.1172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9197    1.0688    1.6414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3478   -2.5146    0.4203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3837    0.4516    0.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3377   -0.9714    0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1870   -1.9255   -1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1929   -0.5576   -1.9569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6947    1.8115   -0.5900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0166    1.7665   -1.1992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3262    1.9587   -2.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4346   -1.6010   -1.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9126    0.2571   -3.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2483    1.3895   -1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5656    0.5115   -1.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8872   -1.1409   -1.2766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1141   -1.7232    0.7572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5541   -0.4388    3.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6980    2.2687    0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
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 20 21  1  0
 21 22  1  0
 22 26  2  0
 26 25  1  0
 25 24  1  0
 24 23  2  0
  7  6  1  0
  6  5  2  0
  5 27  1  0
 27 28  1  0
 28 29  2  0
 28  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
 23 22  1  0
  3  5  1  0
  8 36  1  0
  8 37  1  0
  8 38  1  0
  7 35  1  6
  9 39  1  0
  9 40  1  0
 10 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 16 51  1  0
 16 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
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 20 57  1  0
 20 58  1  0
 21 59  1  0
 21 60  1  0
 26 63  1  0
 24 62  1  0
 23 61  1  0
  6 34  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  4 33  1  0
M  END


  Mrv1652309052203292D          

 29 30  0  0  1  0            999 V2000
   -1.4133  -10.3486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9283   -9.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1833   -8.8965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9679   -8.6416    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5158   -8.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5158   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1986   -7.1741    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1986   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9131   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6276   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3420   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0565   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7710   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4855   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1999   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9144   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6289   -7.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433   -7.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3433   -6.3491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0578   -5.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1440   -5.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9510   -4.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3635   -5.6590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115   -6.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516   -8.8965    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1033   -9.6811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3816  -10.3486    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
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  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
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  2  0  0  0  0
  5 27  1  0  0  0  0
 27 28  1  0  0  0  0
  2 28  1  0  0  0  0
 28 29  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331317

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H](CCC\C(C)=C\CC\C(C)=C\CCC1=COC=C1)\C=C1/OC(=O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O4/c1-18(8-5-9-19(2)11-7-13-22-14-15-28-17-22)10-6-12-20(3)16-23-24(26)21(4)25(27)29-23/h8,11,14-17,20,26H,5-7,9-10,12-13H2,1-4H3/b18-8+,19-11+,23-16-/t20-/m0/s1

> <INCHI_KEY>
HPVSJNGZYYDDMU-CHVWLSOJSA-N

> <FORMULA>
C25H34O4

> <MOLECULAR_WEIGHT>
398.543

> <EXACT_MASS>
398.245709575

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
47.730685656188804

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z)-5-[(2S,6E,10E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-4-hydroxy-3-methyl-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
6.526931795000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.070697596279269

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7866162361015285

> <JCHEM_POLAR_SURFACE_AREA>
59.67000000000001

> <JCHEM_REFRACTIVITY>
121.0992

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-5-[(2S,6E,10E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-4-hydroxy-3-methylfuran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.638 -19.317   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.733 -18.071   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.209 -16.607   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -3.673 -16.131   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.963 -15.702   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.963 -14.162   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.371 -13.392   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.371 -11.852   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.704 -14.162   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.038 -13.392   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.372 -14.162   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.705 -13.392   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.705 -11.852   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.039 -14.162   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.373 -13.392   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.707 -14.162   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.040 -13.392   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.040 -11.852   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.374 -14.162   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.708 -13.392   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.708 -11.852   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      15.041 -11.082   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.202  -9.550   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.709  -9.230   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      17.479 -10.564   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      16.448 -11.708   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.283 -16.607   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.193 -18.071   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.712 -19.317   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   27                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27    5   28                                                       
CONECT   28   27    2   29                                                  
CONECT   29   28                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

View in JSmol

Synonyms

Value	Source
(7E,12E,18S,20Z)-Variabilin	MeSH

Chemical Formula

C₂₅H₃₄O₄

Average Mass

398.5430 Da

Monoisotopic Mass

398.24571 Da

IUPAC Name

(5Z)-5-[(2S,6E,10E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-4-hydroxy-3-methyl-2,5-dihydrofuran-2-one

Traditional Name

(5Z)-5-[(2S,6E,10E)-13-(furan-3-yl)-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-4-hydroxy-3-methylfuran-2-one

CAS Registry Number

Not Available

SMILES

C[C@@H](CCC\C(C)=C\CC\C(C)=C\CCC1=COC=C1)\C=C1/OC(=O)C(C)=C1O

InChI Identifier

InChI=1S/C25H34O4/c1-18(8-5-9-19(2)11-7-13-22-14-15-28-17-22)10-6-12-20(3)16-23-24(26)21(4)25(27)29-23/h8,11,14-17,20,26H,5-7,9-10,12-13H2,1-4H3/b18-8+,19-11+,23-16-/t20-/m0/s1

InChI Key

HPVSJNGZYYDDMU-CHVWLSOJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3CN, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CD3OD, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 151 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CDCl3, experimental)	a.salim@uq.edu.au	Not Available	Not Available	2022-12-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.08 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.91 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150.91 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.08 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600.08 MHz, CD₃CN, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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

Not Available

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
Diterpenoid
2-furanone
Dihydrofuran
Enol ester
Furan
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Heteroaromatic compound
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Enol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	6.53	ChemAxon
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	59.67 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	121.1 m³·mol⁻¹	ChemAxon
Polarizability	47.73 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

10474868

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54682873

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lerata MS, D'Souza S, Sibuyi NRS, Dube A, Meyer M, Samaai T, Antunes EM, Beukes DR: Encapsulation of Variabilin in Stearic Acid Solid Lipid Nanoparticles Enhances Its Anticancer Activity in Vitro. Molecules. 2020 Feb 14;25(4):830. doi: 10.3390/molecules25040830. [PubMed:32074951 ]
Stewart M, Depree C, Thompson KJ: Antifouling sesterterpenes from the New Zealand marine sponge Semitaspongia bactriana. Nat Prod Commun. 2009 Mar;4(3):331-6. [PubMed:19413109 ]

Showing NP-Card for (7E,12E,20Z,18S)-Variabilin (NP0331317)

MOL for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

3D MOL for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

3D SDF for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

3D-SDF for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

PDB for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

3D PDB for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

SMILES for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

INCHI for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

Structure for NP0331317 ((7E,12E,20Z,18S)-Variabilin)

3D Structure for NP0331317 ((7E,12E,20Z,18S)-Variabilin)