NP-MRD: Showing NP-Card for 8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+ (NP0031276)

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Record Information

Version

2.0

Created at

2021-06-19 22:24:19 UTC

Updated at

2021-06-29 23:59:45 UTC

NP-MRD ID

NP0031276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+

Provided By

JEOL Database JEOL Logo

Description

(Z)-2-Methyl-4-acetoxy-2-butenoic acid (3aR,4S,6E,10Z,11aR)-2-oxo-3-methylene-6-methyl-10-(hydroxymethyl)-2,3,3a,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4-yl ester 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. 8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+ is found in Centaurea aspera. 8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+ was first documented in 2005 (Marco, J. A., et al.). Based on a literature review very few articles have been published on (Z)-2-Methyl-4-acetoxy-2-butenoic acid (3aR,4S,6E,10Z,11aR)-2-oxo-3-methylene-6-methyl-10-(hydroxymethyl)-2,3,3a,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4-yl ester.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202100243D          

 57 58  0  0  0  0            999 V2000
    3.2356    1.5209   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371    2.0868   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2214    2.3866   -0.1885 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5200    2.6826    0.5077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7684    2.4763    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9702    2.8559    0.8661 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7076    1.6846    1.1704 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3926   -0.7502    4.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
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  5  3  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306202100243D          

 57 58  0  0  0  0            999 V2000
    3.2356    1.5209   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371    2.0868   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7576    3.4514   -0.5236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5724    4.2570   -0.9308 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163    3.6520   -0.4314 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6593   -1.9635    2.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    0.3985    3.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7810    1.5973    0.6554 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4798    0.5325    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    2.0537   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    1.9442   -1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    3.1238    1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998    3.3523    1.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6170    3.5418    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1952    1.2310    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0755    2.3133   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    2.3530   -2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    0.1046   -2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857   -0.0534   -0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -0.2528   -3.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745   -0.6193   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762   -1.3895   -3.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6174   -2.2385   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5455   -0.1436    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962   -1.6365    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4619   -0.4819    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -1.6332    6.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -2.1999    4.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -0.5755    5.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -0.9711    6.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901    0.4085    5.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    0.7396    3.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5179   -1.6457    2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.5587    2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228   -2.5555    3.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    2.0419    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  7  6  1  0  0  0  0
  2  1  2  3  0  0  0
 29 17  1  0  0  0  0
  3  4  2  0  0  0  0
 17 16  1  0  0  0  0
 14 15  1  0  0  0  0
  8  7  2  0  0  0  0
 17 18  1  0  0  0  0
 29  2  1  0  0  0  0
  8  9  1  0  0  0  0
 18 19  1  0  0  0  0
 14 13  2  0  0  0  0
 19 21  1  0  0  0  0
  9 10  1  0  0  0  0
 21 23  2  0  0  0  0
 29  6  1  0  0  0  0
 23 24  1  0  0  0  0
 19 20  2  0  0  0  0
 12 11  1  0  0  0  0
 24 25  1  0  0  0  0
 12 13  1  0  0  0  0
 25 26  1  0  0  0  0
 11  8  1  0  0  0  0
 26 27  1  0  0  0  0
 14 16  1  0  0  0  0
 26 28  2  0  0  0  0
  6  5  1  0  0  0  0
 21 22  1  0  0  0  0
 12 39  1  0  0  0  0
 12 40  1  0  0  0  0
 11 37  1  0  0  0  0
 11 38  1  0  0  0  0
 13 41  1  0  0  0  0
  7 33  1  0  0  0  0
 17 47  1  6  0  0  0
 16 45  1  0  0  0  0
 16 46  1  0  0  0  0
  9 34  1  0  0  0  0
  9 35  1  0  0  0  0
 10 36  1  0  0  0  0
 29 57  1  1  0  0  0
  6 32  1  6  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
 15 42  1  0  0  0  0
 15 43  1  0  0  0  0
 15 44  1  0  0  0  0
 23 51  1  0  0  0  0
 24 52  1  0  0  0  0
 24 53  1  0  0  0  0
 27 54  1  0  0  0  0
 27 55  1  0  0  0  0
 27 56  1  0  0  0  0
 22 48  1  0  0  0  0
 22 49  1  0  0  0  0
 22 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0031276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])C1=C([H])/[C@@]2([H])OC(=O)C(=C([H])[H])[C@]2([H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])OC(=O)C([H])([H])[H])\C([H])([H])[H])C([H])([H])\C(=C([H])/C([H])([H])C\1([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O7/c1-13-6-5-7-17(12-23)11-19-20(15(3)22(26)29-19)18(10-13)28-21(25)14(2)8-9-27-16(4)24/h6,8,11,18-20,23H,3,5,7,9-10,12H2,1-2,4H3/b13-6-,14-8-,17-11+/t18-,19+,20+/m0/s1

> <INCHI_KEY>
GNIAWQVTXAZHNK-JRIGKPSLSA-N

> <FORMULA>
C22H28O7

> <MOLECULAR_WEIGHT>
404.459

> <EXACT_MASS>
404.183503242

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.2357152905095

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.563525178333333

> <ALOGPS_LOGS>
-4.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.146345517487177

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7347884706510843

> <JCHEM_POLAR_SURFACE_AREA>
99.13000000000002

> <JCHEM_REFRACTIVITY>
108.04779999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 58  0  0  0  0  0  0  0  0999 V2000
    3.2356    1.5209   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0371    2.0868   -0.0080 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.1211    0.4004   -1.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8474   -0.1868   -1.9751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762   -0.6344   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3862   -1.2527   -2.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6656   -0.5935    0.2178 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963    0.0642    0.8143 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5018   -0.2345    2.2437 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489   -0.3852    2.9413 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -0.2879    2.4746 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3926   -0.7502    4.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6044   -1.3204    5.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2225   -0.6255    5.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -0.0461    4.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690   -1.1303    4.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9313   -0.7550    3.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6593   -1.9635    2.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    0.3985    3.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7810    1.5973    0.6554 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4798    0.5325    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    2.0537   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    1.9442   -1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6170    3.5418    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.0755    2.3133   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    2.3530   -2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    0.1046   -2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857   -0.0534   -0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -0.2528   -3.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745   -0.6193   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762   -1.3895   -3.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6174   -2.2385   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5455   -0.1436    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962   -1.6365    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4619   -0.4819    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -1.6332    6.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -2.1999    4.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -0.5755    5.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -0.9711    6.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901    0.4085    5.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    0.7396    3.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5179   -1.6457    2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.5587    2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228   -2.5555    3.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    2.0419    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  2  1  0
  7  6  1  0
  2  1  2  3
 29 17  1  0
  3  4  2  0
 17 16  1  0
 14 15  1  0
  8  7  2  0
 17 18  1  0
 29  2  1  0
  8  9  1  0
 18 19  1  0
 14 13  2  0
 19 21  1  0
  9 10  1  0
 21 23  2  0
 29  6  1  0
 23 24  1  0
 19 20  2  0
 12 11  1  0
 24 25  1  0
 12 13  1  0
 25 26  1  0
 11  8  1  0
 26 27  1  0
 14 16  1  0
 26 28  2  0
  6  5  1  0
 21 22  1  0
 12 39  1  0
 12 40  1  0
 11 37  1  0
 11 38  1  0
 13 41  1  0
  7 33  1  0
 17 47  1  6
 16 45  1  0
 16 46  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 29 57  1  1
  6 32  1  6
  1 30  1  0
  1 31  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 27 54  1  0
 27 55  1  0
 27 56  1  0
 22 48  1  0
 22 49  1  0
 22 50  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       3.236   1.521  -0.195  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.037   2.087  -0.008  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.758   3.451  -0.524  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.572   4.257  -0.931  0.00  0.00           O+0
HETATM    5  O   UNK     0       0.416   3.652  -0.431  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.221   2.387  -0.189  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.520   2.683   0.508  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.768   2.476   0.037  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.970   2.856   0.866  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.708   1.685   1.170  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.089   1.933  -1.344  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.121   0.400  -1.419  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.847  -0.187  -1.975  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.776  -0.634  -1.289  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.386  -1.253  -2.024  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.666  -0.594   0.218  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.596   0.064   0.814  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.502  -0.235   2.244  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.649  -0.385   2.941  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.773  -0.288   2.475  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.393  -0.750   4.368  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.604  -1.320   5.056  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.223  -0.626   5.029  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.076  -0.046   4.559  0.00  0.00           C+0
HETATM   25  O   UNK     0      -1.869  -1.130   4.073  0.00  0.00           O+0
HETATM   26  C   UNK     0      -2.931  -0.755   3.316  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.659  -1.964   2.813  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.255   0.399   3.062  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.781   1.597   0.655  0.00  0.00           C+0
HETATM   30  H   UNK     0       3.480   0.533   0.178  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.031   2.054  -0.712  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.374   1.944  -1.174  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.411   3.124   1.498  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.700   3.352   1.804  0.00  0.00           H+0
HETATM   35  H   UNK     0      -4.617   3.542   0.310  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.195   1.231   1.874  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.075   2.313  -1.642  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.400   2.353  -2.088  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.926   0.105  -2.105  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.386  -0.053  -0.458  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.834  -0.253  -3.064  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.274  -0.619  -1.943  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.176  -1.389  -3.090  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.617  -2.239  -1.607  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.546  -0.144   0.686  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.696  -1.637   0.567  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.462  -0.482   0.424  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.388  -1.633   6.084  0.00  0.00           H+0
HETATM   49  H   UNK     0       2.973  -2.200   4.518  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.406  -0.576   5.102  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.183  -0.971   6.061  0.00  0.00           H+0
HETATM   52  H   UNK     0      -1.590   0.409   5.414  0.00  0.00           H+0
HETATM   53  H   UNK     0      -0.934   0.740   3.810  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.518  -1.646   2.215  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.995  -2.559   2.182  0.00  0.00           H+0
HETATM   56  H   UNK     0      -4.023  -2.555   3.657  0.00  0.00           H+0
HETATM   57  H   UNK     0       0.803   2.042   1.663  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    3    1   29                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    7   29    5   32                                             
CONECT    7    6    8   33                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10   34   35                                             
CONECT   10    9   36                                                       
CONECT   11   12    8   37   38                                             
CONECT   12   11   13   39   40                                             
CONECT   13   14   12   41                                                  
CONECT   14   15   13   16                                                  
CONECT   15   14   42   43   44                                             
CONECT   16   17   14   45   46                                             
CONECT   17   29   16   18   47                                             
CONECT   18   17   19                                                       
CONECT   19   18   21   20                                                  
CONECT   20   19                                                            
CONECT   21   19   23   22                                                  
CONECT   22   21   48   49   50                                             
CONECT   23   21   24   51                                                  
CONECT   24   23   25   52   53                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   54   55   56                                             
CONECT   28   26                                                            
CONECT   29   17    2    6   57                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34    9                                                            
CONECT   35    9                                                            
CONECT   36   10                                                            
CONECT   37   11                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   13                                                            
CONECT   42   15                                                            
CONECT   43   15                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   16                                                            
CONECT   47   17                                                            
CONECT   48   22                                                            
CONECT   49   22                                                            
CONECT   50   22                                                            
CONECT   51   23                                                            
CONECT   52   24                                                            
CONECT   53   24                                                            
CONECT   54   27                                                            
CONECT   55   27                                                            
CONECT   56   27                                                            
CONECT   57   29                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  116    0
END

RDKit          3D

57 58  0  0  0  0  0  0  0  0999 V2000
    3.2356    1.5209   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2225   -0.6255    5.0290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0762   -0.0461    4.5588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8690   -1.1303    4.0729 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9313   -0.7550    3.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6593   -1.9635    2.8135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2545    0.3985    3.0623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7810    1.5973    0.6554 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4798    0.5325    0.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    2.0537   -0.7117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    1.9442   -1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4110    3.1238    1.4984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6998    3.3523    1.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6170    3.5418    0.3096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1952    1.2310    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0755    2.3133   -1.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3996    2.3530   -2.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    0.1046   -2.1046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857   -0.0534   -0.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8337   -0.2528   -3.0638 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745   -0.6193   -1.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762   -1.3895   -3.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6174   -2.2385   -1.6074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5455   -0.1436    0.6855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6962   -1.6365    0.5667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4619   -0.4819    0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3882   -1.6332    6.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9732   -2.1999    4.5178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -0.5755    5.1019 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1833   -0.9711    6.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5901    0.4085    5.4142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    0.7396    3.8102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5179   -1.6457    2.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9954   -2.5587    2.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228   -2.5555    3.6571 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    2.0419    1.6630 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0
  3  2  1  0
  7  6  1  0
  2  1  2  3
 29 17  1  0
  3  4  2  0
 17 16  1  0
 14 15  1  0
  8  7  2  0
 17 18  1  0
 29  2  1  0
  8  9  1  0
 18 19  1  0
 14 13  2  0
 19 21  1  0
  9 10  1  0
 21 23  2  0
 29  6  1  0
 23 24  1  0
 19 20  2  0
 12 11  1  0
 24 25  1  0
 12 13  1  0
 25 26  1  0
 11  8  1  0
 26 27  1  0
 14 16  1  0
 26 28  2  0
  6  5  1  0
 21 22  1  0
 12 39  1  0
 12 40  1  0
 11 37  1  0
 11 38  1  0
 13 41  1  0
  7 33  1  0
 17 47  1  6
 16 45  1  0
 16 46  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 29 57  1  1
  6 32  1  6
  1 30  1  0
  1 31  1  0
 15 42  1  0
 15 43  1  0
 15 44  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 27 54  1  0
 27 55  1  0
 27 56  1  0
 22 48  1  0
 22 49  1  0
 22 50  1  0
M  END

View in JSmol

Synonyms

Value	Source
(Z)-2-Methyl-4-acetoxy-2-butenoate (3ar,4S,6E,10Z,11ar)-2-oxo-3-methylene-6-methyl-10-(hydroxymethyl)-2,3,3a,4,5,8,9,11aalpha-octahydrocyclodeca[b]furan-4-yl ester	Generator

Chemical Formula

C₂₂H₂₈O₇

Average Mass

404.4590 Da

Monoisotopic Mass

404.18350 Da

IUPAC Name

(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate

Traditional Name

(3aR,4S,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-4-yl (2Z)-4-(acetyloxy)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

[H]OC([H])([H])C1=C([H])/[C@@]2([H])OC(=O)C(=C([H])[H])[C@]2([H])[C@@]([H])(OC(=O)C(=C(\[H])C([H])([H])OC(=O)C([H])([H])[H])\C([H])([H])[H])C([H])([H])\C(=C([H])/C([H])([H])C\1([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C22H28O7/c1-13-6-5-7-17(12-23)11-19-20(15(3)22(26)29-19)18(10-13)28-21(25)14(2)8-9-27-16(4)24/h6,8,11,18-20,23H,3,5,7,9-10,12H2,1-2,4H3/b13-6-,14-8-,17-11+/t18-,19+,20+/m0/s1

InChI Key

GNIAWQVTXAZHNK-JRIGKPSLSA-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
Centaurea aspera	JEOL database	Marco, J. A., et al, Phytochemistry 66, 1644 (2005)

Chemical Taxonomy

Classification

Not classified

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	1.89	ALOGPS
logP	2.56	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.05 m³·mol⁻¹	ChemAxon
Polarizability	42.24 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101763073

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Marco, J. A., et al. (2005). Marco, J. A., et al, Phytochemistry 66, 1644 (2005) . Phytochem..

Showing NP-Card for 8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+ (NP0031276)

MOL for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

3D MOL for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

3D SDF for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

3D-SDF for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

PDB for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

3D PDB for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

SMILES for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

INCHI for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

Structure for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)

3D Structure for NP0031276 (8alpha-(Z-2-methyl-4-acetoxybut-2-enoyloxy)-15-hydroxygermacra-1(10),E,4Z+)