NP-MRD: Showing NP-Card for Rotundin (NP0044178)

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Record Information

Version

1.0

Created at

2021-11-12 23:54:32 UTC

Updated at

2021-11-26 17:46:18 UTC

NP-MRD ID

NP0044178

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Rotundin

Description

ROTUNDIN belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Rotundin is found in Tithonia rotundifolia, Trithonia rotundifolia and Aldama robusta. It was first documented in 2009 (PMID: 19309764). Based on a literature review very few articles have been published on ROTUNDIN.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652311132100542D          

 30 32  0  0  1  0            999 V2000
    2.9158    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571    1.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    1.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5416    0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3544    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.1112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -0.8856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8260   -0.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.3929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9234   -1.1673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4518   -0.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -1.6600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0537   -2.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9563   -1.3784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4847   -0.7448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0455   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    0.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120    0.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -1.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3382   -3.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8666   -2.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798    0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542    0.7045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0614    2.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4694    1.8019    0.0000 C   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
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  1  0  0  0
 15 24  1  0  0  0  0
 14 25  1  1  0  0  0
 10 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END

     RDKit          3D

 58 60  0  0  0  0  0  0  0  0999 V2000
    2.8128   -0.8223   -2.8046 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7485   -1.3755   -2.3065 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4094   -2.8005   -2.4063 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892   -3.7228   -2.8513 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1150   -2.9587   -1.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0259   -1.9414   -0.9210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1437   -2.0216   -0.1308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3588   -1.7233   -0.5021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5494   -1.8933    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150   -1.2477   -1.8535 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8691   -1.8616   -2.2168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0123    0.2398   -1.9097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8419    1.0935   -1.6031 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9242    2.3509   -0.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    1.1993   -0.3190 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4483    1.1808    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539    2.4023    1.6119 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9721    2.7037    2.7581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7948    3.9629    3.5160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8130    1.8698    3.1741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1175    0.9622    0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9281    0.4060   -0.7852 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1092    0.1289   -0.0459 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    0.8208   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3576    1.8572   -0.6931 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4201    0.4291    0.7880 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6689    1.2553    0.7750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498   -0.6480    1.5561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627   -1.5118    1.6232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5795   -0.7805   -1.5894 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9872    0.2120   -2.7557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5664   -1.4511   -3.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8774   -2.2835   -0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1072   -2.3688    0.9375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8931   -2.9409    0.2836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2287   -1.8153    1.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3626   -1.2227    0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737   -1.5677   -2.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0163   -1.7947   -3.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3660    0.4396   -2.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8811    0.3702   -1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2515    1.3067   -2.5259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1836    0.3762    1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4813    1.1121    0.6028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2089    3.8597    4.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4132    4.7383    2.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7272    4.2780    3.5561 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2986    1.9587    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1358    0.2520    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2041    1.2558   -1.4239 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0423    1.2910    1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4244    0.8293    0.0717 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3700    2.2710    0.4433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3230   -0.8913    2.1226 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1025   -1.8931    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -2.4114    2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3504   -0.9935    1.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0262   -0.4704   -2.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 28  1  0
 28 26  2  0
 26 27  1  0
 26 24  1  0
 24 25  2  0
 24 23  1  0
 23 22  1  0
 22 21  1  0
 21 15  1  0
 15 13  1  0
 13 14  1  0
 13 12  1  0
 12 10  1  0
 10  8  1  0
  8  7  2  0
  7  6  1  0
  6 30  1  0
 30  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  8  9  1  0
 10 11  1  0
 15 16  1  1
 16 17  1  0
 17 18  1  0
 18 20  2  0
 18 19  1  0
 30 22  1  0
 14 15  1  0
  5  6  1  0
 29 55  1  0
 29 56  1  0
 29 57  1  0
 28 54  1  0
 27 51  1  0
 27 52  1  0
 27 53  1  0
 22 50  1  6
 21 48  1  0
 21 49  1  0
 13 42  1  6
 12 40  1  0
 12 41  1  0
 10 38  1  6
  7 34  1  0
  6 33  1  1
 30 58  1  6
  1 31  1  0
  1 32  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 11 39  1  0
 16 43  1  0
 16 44  1  0
 19 45  1  0
 19 46  1  0
 19 47  1  0
M  END


  Mrv1652311132100542D          

 30 32  0  0  1  0            999 V2000
    2.9158    0.8040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4442    1.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2571    1.2967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7855    1.9303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5416    0.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3544    0.3815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0132   -0.1112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -0.8856    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8260   -0.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6389   -0.3929    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9234   -1.1673    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4518   -0.5337    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3950   -1.8008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5821   -1.6600    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0537   -2.2936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2408   -2.1528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9563   -1.3784    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4847   -0.7448    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0455   -0.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3522    0.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2456   -0.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6120    0.2799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905   -1.0716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3382   -3.0680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8666   -2.4344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7798    0.4200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542    0.7045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6950    1.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0614    2.0458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4694    1.8019    0.0000 C   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
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 10 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 17 23  1  1  0  0  0
 15 24  1  0  0  0  0
 14 25  1  1  0  0  0
 10 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044178

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O8/c1-6-11(2)20(25)29-17-9-22(10-27-14(5)23)18(30-22)8-15(24)12(3)7-16-19(17)13(4)21(26)28-16/h6-7,15-19,24H,4,8-10H2,1-3,5H3/b11-6-,12-7-/t15-,16+,17+,18+,19-,22-/m0/s1

> <INCHI_KEY>
UELPQYXGRIZTHA-XSEBJXQCSA-N

> <FORMULA>
C22H28O8

> <MOLECULAR_WEIGHT>
420.458

> <EXACT_MASS>
420.178417862

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.905292349206185

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2R,4S,6R,8S,9Z,11R)-4-[(acetyloxy)methyl]-8-hydroxy-9-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.97

> <JCHEM_LOGP>
1.8009769376666669

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.524255064998155

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006890834569801

> <JCHEM_POLAR_SURFACE_AREA>
111.66

> <JCHEM_REFRACTIVITY>
106.23089999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,6R,8S,9Z,11R)-4-[(acetyloxy)methyl]-8-hydroxy-9-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-NOV-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-NOV-21         0                                  
HETATM    1  C   UNK     0       5.443   1.501   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.429   2.683   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.947   2.421   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.933   3.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.478   0.975   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.995   0.712   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.491  -0.208   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.022  -1.653   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.009  -0.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.526  -0.733   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.057  -2.179   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.043  -0.996   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      10.071  -3.362   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.553  -3.099   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.567  -4.281   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.050  -4.019   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.519  -2.573   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.505  -1.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.685  -0.087   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.257   1.343   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.192  -0.464   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       3.009   0.523   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.089  -2.000   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       8.098  -5.727   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.084  -4.544   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.789   0.784   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.234   1.315   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      12.497   2.832   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.315   3.819   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      13.943   3.364   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   26                                             
CONECT   11   10   12   13                                                  
CONECT   12   11   10                                                       
CONECT   13   11   14                                                       
CONECT   14   13   15   25                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   23                                                  
CONECT   18   17    8   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   17                                                       
CONECT   24   15                                                            
CONECT   25   14                                                            
CONECT   26   10   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₂H₂₈O₈

Average Mass

420.4580 Da

Monoisotopic Mass

420.17842 Da

IUPAC Name

(1R,2R,4S,6R,8S,9Z,11R)-4-[(acetyloxy)methyl]-8-hydroxy-9-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(1R,2R,4S,6R,8S,9Z,11R)-4-[(acetyloxy)methyl]-8-hydroxy-9-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0^{4,6}]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(\C)C(=O)O[C@@H]1C[C@@]2(COC(C)=O)O[C@@H]2C[C@H](O)\C(C)=C/[C@H]2OC(=O)C(=C)[C@H]12

InChI Identifier

InChI=1S/C22H28O8/c1-6-11(2)20(25)29-17-9-22(10-27-14(5)23)18(30-22)8-15(24)12(3)7-16-19(17)13(4)21(26)28-16/h6-7,15-19,24H,4,8-10H2,1-3,5H3/b11-6-,12-7-/t15-,16+,17+,18+,19-,22-/m0/s1

InChI Key

UELPQYXGRIZTHA-XSEBJXQCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, 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
Tithonia rotundifolia	Plant	KNApSAcK
Trithonia rotundifolia	-	KNApSAcK
Viguiera robusta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Gamma butyrolactone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
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	0.97	ALOGPS
logP	1.8	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.52	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	111.66 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	106.23 m³·mol⁻¹	ChemAxon
Polarizability	42.91 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	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00011887

Chemspider ID

30815215

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73354911

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang Z, Du Q, Qiu X, Liu F, Tan F, Lan K, Jiang X, Jiang Q: Simultaneous determination of six herbal components in intestinal perfusate by high-performance liquid chromatography. Biomed Chromatogr. 2009 Aug;23(8):798-803. doi: 10.1002/bmc.1188. [PubMed:19309764 ]
A. Vivar, A. Pérez, R. Saucedo (1982). Rotundin and (Z)-18-methylsphaerocephalin, two new germacranolides from Tithonia rotundifolia. Phytochemistry, Volume 21, Issue 2, 1982, Pages 375-379. Phytochemistry.

Showing NP-Card for Rotundin (NP0044178)

MOL for NP0044178 (Rotundin)

3D MOL for NP0044178 (Rotundin)

3D SDF for NP0044178 (Rotundin)

3D-SDF for NP0044178 (Rotundin)

PDB for NP0044178 (Rotundin)

3D PDB for NP0044178 (Rotundin)

SMILES for NP0044178 (Rotundin)

INCHI for NP0044178 (Rotundin)

Structure for NP0044178 (Rotundin)

3D Structure for NP0044178 (Rotundin)