NP-MRD: Showing NP-Card for 1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate (NP0328012)

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Record Information

Version

2.0

Created at

2022-09-12 11:05:42 UTC

Updated at

2022-09-12 11:05:42 UTC

NP-MRD ID

NP0328012

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate

Description

Tagitinin F belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. 1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate is found in Tithonia diversifolia. 1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate was first documented in 2012 (PMID: 22986291). Based on a literature review a small amount of articles have been published on Tagitinin F (PMID: 24830711) (PMID: 33212290) (PMID: 31400235).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213052D          

 25 27  0  0  0  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -2.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
  2 24  1  0  0  0  0
  6 24  1  0  0  0  0
 14 25  1  0  0  0  0
 10 25  1  0  0  0  0
M  END

     RDKit          3D

 49 51  0  0  0  0  0  0  0  0999 V2000
    1.3908    2.2120   -1.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4408    2.2277   -1.0587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4260    3.4021   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0654    4.5808   -0.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6296    2.9116   -0.4059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5595    1.4337   -0.4288 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6578    1.1192    0.4930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5204    0.0845    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9036    0.1440    0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1019   -1.0609   -0.5770 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6144   -1.0259   -1.8738 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1421   -2.4156   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8745   -2.8083    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2629   -1.4453    0.5135 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8365   -1.2370    1.8672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1531   -1.2812    0.5341 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5828   -0.0202   -0.2711 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9341    0.1244    0.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0625   -0.3441   -0.3323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9590   -0.9837   -1.4340 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4366   -0.1750    0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8335    1.2554    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4503   -0.9438   -0.6074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1485    1.2021   -0.0919 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7103   -0.8985   -0.6274 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0087    1.3886   -2.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6133    3.1138   -2.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8212    1.2526   -1.5012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8927    1.6576    1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6032    0.6670    0.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8818    0.6240    1.7870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2191   -0.9137    0.9548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0658   -1.8960   -2.0235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0497   -3.0085    0.2048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4416   -3.7717    0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3845   -2.1392    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4455   -0.4280    2.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070   -1.4751    1.9958 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7010   -2.1210    0.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086   -1.1984    1.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6476   -0.3917   -1.2841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4788   -0.6291    1.2446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1799    1.7682    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039    1.7548   -0.6283 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8835    1.2798    0.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9759   -0.2136   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2069   -1.4453    0.0081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8786   -1.6495   -1.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0357    1.7166    0.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 23  1  0
 21 19  1  0
 19 20  2  0
 19 18  1  0
 18 17  1  0
 17 16  1  0
 16 14  1  0
 14 15  1  1
 14 25  1  0
 25 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  2  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  0
  3  2  1  0
  2  1  2  3
  2 24  1  0
 24 17  1  0
 13 14  1  0
 24  6  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 21 42  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 17 41  1  6
 16 39  1  0
 16 40  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
  7 29  1  0
  6 28  1  6
  1 26  1  0
  1 27  1  0
 24 49  1  1
M  END


  Mrv1652309122213052D          

 25 27  0  0  0  0            999 V2000
    5.4278   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6578    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4828    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1729    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    2.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341    1.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    2.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3341   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8492   -1.3349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -1.3349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0527   -2.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376   -2.7560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2322   -2.1748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8967   -2.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7473   -1.5074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6041    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 17 24  1  0  0  0  0
  2 24  1  0  0  0  0
  6 24  1  0  0  0  0
 14 25  1  0  0  0  0
 10 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328012

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC1CC2(C)OC(O)(C=C2)C(C)=CC2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O6/c1-10(2)16(20)24-14-9-18(5)6-7-19(22,25-18)11(3)8-13-15(14)12(4)17(21)23-13/h6-8,10,13-15,22H,4,9H2,1-3,5H3

> <INCHI_KEY>
XJUPOHKZSDZNBE-UHFFFAOYSA-N

> <FORMULA>
C19H24O6

> <MOLECULAR_WEIGHT>
348.395

> <EXACT_MASS>
348.157288493

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.9019187260054

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-9-yl 2-methylpropanoate

> <JCHEM_LOGP>
2.786378629666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.085995801317956

> <JCHEM_PKA_STRONGEST_BASIC>
-4.4513629749549795

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
91.0168

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-9-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      10.132  -1.941   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.656  -0.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.561   0.770   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      12.101   0.770   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       9.656   2.016   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.191   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.286   2.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.822   3.262   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.822   4.802   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.357   2.786   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.452   4.032   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.452   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.452  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.357  -1.246   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.452  -2.492   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.822  -1.722   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.286  -1.246   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.191  -2.492   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.565  -3.899   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.470  -5.145   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.034  -4.060   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.407  -5.466   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.128  -2.814   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.191  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.861   0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   25                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   25                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   24                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   17    2    6                                                  
CONECT   25   14   10                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

View in JSmol

Synonyms

Value	Source
Tagitinin	MeSH
Tagitinin C	MeSH
Tagitinin D	MeSH
Tagitinins	MeSH
Tagitinin a	MeSH
Tagitinin b	MeSH

Chemical Formula

C₁₉H₂₄O₆

Average Mass

348.3950 Da

Monoisotopic Mass

348.15729 Da

IUPAC Name

1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-9-yl 2-methylpropanoate

Traditional Name

1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0^{4,8}]tetradeca-2,12-dien-9-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC1CC2(C)OC(O)(C=C2)C(C)=CC2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C19H24O6/c1-10(2)16(20)24-14-9-18(5)6-7-19(22,25-18)11(3)8-13-15(14)12(4)17(21)23-13/h6-8,10,13-15,22H,4,9H2,1-3,5H3

InChI Key

XJUPOHKZSDZNBE-UHFFFAOYSA-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
Tithonia diversifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

Alternative Parents

Substituents

Dicarboxylic acid or derivatives
Gamma butyrolactone
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Hemiacetal
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.79	ChemAxon
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	91.02 m³·mol⁻¹	ChemAxon
Polarizability	35.9 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

C00003370

Chemspider ID

287677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

324885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

de Toledo JS, Ambrosio SR, Borges CH, Manfrim V, Cerri DG, Cruz AK, Da Costa FB: In vitro leishmanicidal activities of sesquiterpene lactones from Tithonia diversifolia against Leishmania braziliensis promastigotes and amastigotes. Molecules. 2014 May 14;19(5):6070-9. doi: 10.3390/molecules19056070. [PubMed:24830711 ]
Zhao G, Li X, Chen W, Xi Z, Sun L: Three new sesquiterpenes from Tithonia diversifolia and their anti-hyperglycemic activity. Fitoterapia. 2012 Dec;83(8):1590-7. doi: 10.1016/j.fitote.2012.09.007. Epub 2012 Sep 15. [PubMed:22986291 ]
Silva LP, Santos EC, Borges BA, Veloso MP, Chagas-Paula DA, Goncalves RV, Novaes RD: Tagitinin F has anti-inflammatory, anti-nociceptive and anti-matrix metalloproteinase properties: An in silico, in vitro and in vivo study. Pharmacol Res. 2021 Feb;164:105303. doi: 10.1016/j.phrs.2020.105303. Epub 2020 Nov 16. [PubMed:33212290 ]
Fernandes VHC, Viera NB, Zanini LBL, Silva AF, Salem PPO, Soares MG, Nicacio KJ, de Paula ACC, Virtuoso LS, Oliveira TB, Silva EO, Dias DF, Chagas-Paula DA: Fast and Efficient Method to Obtain Tagitinin F by Photocyclization of Tagitinin C. Photochem Photobiol. 2020 Jan;96(1):14-20. doi: 10.1111/php.13148. Epub 2019 Oct 10. [PubMed:31400235 ]
LOTUS database [Link]

Showing NP-Card for 1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate (NP0328012)

MOL for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D MOL for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D SDF for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D-SDF for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

PDB for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D PDB for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

SMILES for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

INCHI for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

Structure for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)

3D Structure for NP0328012 (1-hydroxy-2,11-dimethyl-7-methylidene-6-oxo-5,14-dioxatricyclo[9.2.1.0⁴,⁸]tetradeca-2,12-dien-9-yl 2-methylpropanoate)