NP-MRD: Showing NP-Card for (3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate (NP0217413)

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Record Information

Version

2.0

Created at

2022-09-05 17:45:22 UTC

Updated at

2022-09-05 17:45:22 UTC

NP-MRD ID

NP0217413

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate

Description

Thapsitranstagin belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate is found in Thapsia garganica and Thapsia transtagana. (3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate was first documented in 2007 (PMID: 17669447). Based on a literature review very few articles have been published on Thapsitranstagin.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052219452D          

 44 46  0  0  1  0            999 V2000
    1.6623    8.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    9.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334    8.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    9.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334    8.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    7.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    7.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    6.8831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2804    6.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5042    6.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353    5.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603    5.6136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6153    6.3982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3999    6.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5714    7.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9583    8.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    7.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276    8.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145    9.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    8.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    4.9686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6180    4.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3891    5.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2049    5.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193    6.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    4.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911    4.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    3.8063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9478    2.9813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6623    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6623    1.7438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    2.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    3.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0912    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057    2.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045    4.1642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2415    3.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    4.9686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8007    5.0425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    4.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    4.1003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037    3.7411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9715    3.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648    2.9889    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
  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
  9 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 36 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  1  0  0  0
M  END


  Mrv1652309052219452D          

 44 46  0  0  1  0            999 V2000
    1.6623    8.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    9.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334    8.9456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    9.3581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2334    8.1206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4811    7.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    7.7081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    6.8831    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2804    6.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5042    6.6531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5353    5.6136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3603    5.6136    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6153    6.3982    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3999    6.6531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5714    7.4601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9583    8.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3560    7.7150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5276    8.5220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145    9.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3122    8.7769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8747    4.9686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6180    4.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3891    5.6136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2049    5.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193    6.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5063    4.7226    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6911    4.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9478    3.8063    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9478    2.9813    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6623    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6623    1.7438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    2.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3768    3.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0912    2.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8057    2.9813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045    4.1642    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2415    3.3401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0209    4.9686    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8007    5.0425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1250    4.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293    4.1003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5037    3.7411    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9715    3.0615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1648    2.9889    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
  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
  9 11  2  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 12 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 21 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  1  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 28 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  0  0  0  0
 11 38  1  0  0  0  0
 38 39  1  6  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 40 42  1  0  0  0  0
 36 42  1  0  0  0  0
 42 43  1  6  0  0  0
 42 44  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0217413

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(C)C(=O)O[C@@H]1C[C@@](C)(OC(C)=O)[C@@H]2[C@@H](OC(=O)CC(C)C)[C@H](OC(=O)C(\C)=C/C)C(C)=C2[C@H]2OC(=O)[C@](C)(O)[C@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O12/c1-11-16(5)27(35)40-20-14-30(9,44-19(8)33)23-22(26-32(20,39)31(10,38)29(37)43-26)18(7)24(42-28(36)17(6)12-2)25(23)41-21(34)13-15(3)4/h12,15-16,20,23-26,38-39H,11,13-14H2,1-10H3/b17-12-/t16?,20-,23+,24-,25-,26-,30-,31+,32+/m1/s1

> <INCHI_KEY>
XHFQVCZACDPUSC-OWKZXDOKSA-N

> <FORMULA>
C32H46O12

> <MOLECULAR_WEIGHT>
622.708

> <EXACT_MASS>
622.298926921

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
90

> <JCHEM_AVERAGE_POLARIZABILITY>
65.98879489851754

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,3aS,4R,6R,6aS,7R,8R,9bR)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_LOGP>
3.4362562103333323

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.49869575346963

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.135560013316695

> <JCHEM_PKA_STRONGEST_BASIC>
-4.307629557476353

> <JCHEM_POLAR_SURFACE_AREA>
171.96

> <JCHEM_REFRACTIVITY>
154.53490000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,3aS,4R,6R,6aS,7R,8R,9bR)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate

> <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       3.103  16.698   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.769  17.468   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.436  16.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.898  17.468   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.436  15.158   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.898  14.388   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.769  14.388   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.769  12.848   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.523  11.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.941  12.419   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.999  10.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.539  10.479   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.015  11.943   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.480  12.419   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.800  13.926   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.656  14.956   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.265  14.401   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.585  15.908   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.440  16.938   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.049  16.384   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.499   9.275   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.887   8.606   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.460  10.479   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.982  10.249   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.943  11.453   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.545   8.816   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       3.157   7.773   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.769   7.105   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.769   5.565   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.103   4.795   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.103   3.255   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.437   5.565   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.437   7.105   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.770   4.795   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.104   5.565   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.382   7.773   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.451   6.235   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.039   9.275   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.495   9.413   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -2.100   7.997   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -3.601   7.654   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      -0.940   6.983   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      -1.813   5.715   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      -0.308   5.579   0.000  0.00  0.00           O+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   13                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   38                                                  
CONECT   12   11   13   21                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   12   22   23   27                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   21   28                                                       
CONECT   28   27   29   36                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34                                                            
CONECT   36   28   37   38   42                                             
CONECT   37   36                                                            
CONECT   38   36   11   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   36   43   44                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₆O₁₂

Average Mass

622.7080 Da

Monoisotopic Mass

622.29893 Da

IUPAC Name

(3R,3aS,4R,6R,6aS,7R,8R,9bR)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-2H,3H,3aH,4H,5H,6H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(3R,3aS,4R,6R,6aS,7R,8R,9bR)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4H,5H,6aH,7H,8H,9bH-azuleno[4,5-b]furan-8-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CCC(C)C(=O)O[C@@H]1C[C@@](C)(OC(C)=O)[C@@H]2[C@@H](OC(=O)CC(C)C)[C@H](OC(=O)C(\C)=C/C)C(C)=C2[C@H]2OC(=O)[C@](C)(O)[C@]12O

InChI Identifier

InChI=1S/C32H46O12/c1-11-16(5)27(35)40-20-14-30(9,44-19(8)33)23-22(26-32(20,39)31(10,38)29(37)43-26)18(7)24(42-28(36)17(6)12-2)25(23)41-21(34)13-15(3)4/h12,15-16,20,23-26,38-39H,11,13-14H2,1-10H3/b17-12-/t16?,20-,23+,24-,25-,26-,30-,31+,32+/m1/s1

InChI Key

XHFQVCZACDPUSC-OWKZXDOKSA-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
Thapsia garganica	LOTUS Database	35616633
Thapsia transtagana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Lactone
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.44	ChemAxon
pKa (Strongest Acidic)	11.14	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	171.96 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	154.53 m³·mol⁻¹	ChemAxon
Polarizability	65.99 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00034723

Chemspider ID

4572547

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5458630

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rubal JJ, Moreno-Dorado FJ, Guerra FM, Jorge ZD, Saouf A, Akssira M, Mellouki F, Romero-Garrido R, Massanet GM: A pyran-2-one and four meroterpenoids from Thapsia transtagana and their implication in the biosynthesis of transtaganolides. Phytochemistry. 2007 Oct;68(19):2480-6. doi: 10.1016/j.phytochem.2007.06.023. Epub 2007 Jul 31. [PubMed:17669447 ]
LOTUS database [Link]

Showing NP-Card for (3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate (NP0217413)

MOL for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D MOL for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D SDF for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D-SDF for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

PDB for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D PDB for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

SMILES for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

INCHI for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

Structure for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)

3D Structure for NP0217413 ((3r,3as,4r,6r,6as,7r,8r,9br)-6-(acetyloxy)-3,3a-dihydroxy-3,6,9-trimethyl-4-[(2-methylbutanoyl)oxy]-7-[(3-methylbutanoyl)oxy]-2-oxo-4h,5h,6ah,7h,8h,9bh-azuleno[4,5-b]furan-8-yl (2z)-2-methylbut-2-enoate)