NP-MRD: Showing NP-Card for (1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate (NP0254929)

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Record Information

Version

2.0

Created at

2022-09-07 19:14:50 UTC

Updated at

2022-09-07 19:14:51 UTC

NP-MRD ID

NP0254929

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate

Description

(1R,2S,3S,4R,5R,7S,8S,9S,10S,11R,12R,14S,15S)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]Octadecan-15-yl benzoate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. (1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate is found in Euphorbia prolifera. Based on a literature review very few articles have been published on (1R,2S,3S,4R,5R,7S,8S,9S,10S,11R,12R,14S,15S)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]Octadecan-15-yl benzoate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072221142D          

 49 54  0  0  1  0            999 V2000
    8.1652    3.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3568    3.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0948    2.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414    1.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2704    2.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6262    1.6756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8045    1.6027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3664    2.3018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6886    3.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075    3.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212    4.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1168    4.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624    2.4865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8632    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    1.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1166    0.5453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4831   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207    0.3606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1177   -0.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0149   -1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6751   -1.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2563   -1.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198    0.7986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7977   -0.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275    0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495    0.9166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7866    0.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5783    1.6616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8719    1.2354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1496    1.6341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7509    0.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    0.5131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0684   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778   -0.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -0.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784   -1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966   -0.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1337    2.4589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3326    2.8723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390    3.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3492    3.9342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402    4.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516    5.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528    5.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9426    5.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313    4.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301    4.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401    2.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480    3.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  5  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  6  0  0  0
 16 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  6  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 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
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
 38 48  1  0  0  0  0
 13 48  1  0  0  0  0
 48 49  2  0  0  0  0
M  END


  Mrv1652309072221142D          

 49 54  0  0  1  0            999 V2000
    8.1652    3.3764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3568    3.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0948    2.4298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6414    1.8118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2704    2.2622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6262    1.6756    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8045    1.6027    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.3664    2.3018    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6886    3.1133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5075    3.9370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7212    4.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1168    4.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5624    2.4865    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8632    2.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5797    1.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1166    0.5453    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4831   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9207    0.3606    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1177   -0.5668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0149   -1.4231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6751   -1.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2563   -1.7474    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6198    0.7986    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7977   -0.0560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3275    0.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9495    0.9166    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.7866    0.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5783    1.6616    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8719    1.2354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1496    1.6341    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7509    0.9118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4732    0.5131    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0684   -0.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8778   -0.2322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0259   -0.5372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8784   -1.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3966   -0.0036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1337    2.4589    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3326    2.8723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390    3.6960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3492    3.9342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7402    4.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5516    5.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528    5.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9426    5.3909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1313    4.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5301    4.0228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8401    2.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9480    3.7592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  6  5  1  6  0  0  0
  7  6  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  1  6  0  0  0
 16 28  1  0  0  0  0
 13 28  1  0  0  0  0
 28 29  1  6  0  0  0
 29 30  1  6  0  0  0
 30 31  1  6  0  0  0
 31 32  1  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 30 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
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 42 47  1  0  0  0  0
 38 48  1  0  0  0  0
 13 48  1  0  0  0  0
 48 49  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0254929

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)O[C@@H]1[C@H](C)C[C@]2(O)[C@@H]1[C@H](OC(C)=O)[C@]13CO[C@@](C)([C@H]1[C@H]1[C@H](C[C@@]1(C)OC(C)=O)[C@H](OC(=O)C1=CC=CC=C1)C3=O)[C@H]2OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C36H44O13/c1-8-23(40)47-26-17(2)14-36(43)25(26)30(45-18(3)37)35-16-44-34(7,32(36)46-19(4)38)28(35)24-22(15-33(24,6)49-20(5)39)27(29(35)41)48-31(42)21-12-10-9-11-13-21/h9-13,17,22,24-28,30,32,43H,8,14-16H2,1-7H3/t17-,22+,24-,25+,26-,27+,28-,30+,32-,33-,34+,35-,36+/m1/s1

> <INCHI_KEY>
OBGLBABTPRECCH-ADUXVFRQSA-N

> <FORMULA>
C36H44O13

> <MOLECULAR_WEIGHT>
684.735

> <EXACT_MASS>
684.278191477

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
69.65509081350241

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4R,5R,7S,8S,9S,10S,11R,12R,14S,15S)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0^{1,10}.0^{3,7}.0^{11,14}]octadecan-15-yl benzoate

> <JCHEM_LOGP>
2.4509055116666687

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.34565257101272

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.33528707516004

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5267589121581464

> <JCHEM_POLAR_SURFACE_AREA>
178.02999999999997

> <JCHEM_REFRACTIVITY>
166.11499999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4R,5R,7S,8S,9S,10S,11R,12R,14S,15S)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0^{1,10}.0^{3,7}.0^{11,14}]octadecan-15-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      15.242   6.303   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.733   5.996   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.244   4.536   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      14.264   3.382   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      11.705   4.223   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.502   3.128   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.968   2.992   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.151   4.297   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.752   5.812   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       8.414   7.349   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.946   7.815   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.551   8.387   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.650   4.641   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.345   3.824   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.816   2.207   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.818   1.018   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.635  -0.385   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.319   0.673   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.686  -1.058   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       7.494  -2.656   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.727  -3.580   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.078  -3.262   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.624   1.491   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.956  -0.105   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.945   0.699   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.106   1.711   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.668   1.345   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.679   3.102   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.361   2.306   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.013   3.050   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.268   1.702   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.617   0.958   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.728  -0.410   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.505  -0.433   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.915  -1.003   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.640  -2.518   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       0.740  -0.007   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.983   4.590   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.487   5.362   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.126   6.899   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       0.652   7.344   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.248   7.954   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.896   9.453   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.018  10.508   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.493  10.063   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       5.845   8.564   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.723   7.509   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       5.301   5.386   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       5.503   7.017   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                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14   28   48                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   28                                             
CONECT   17   16                                                            
CONECT   18   16   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18    7   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25    6   27                                                  
CONECT   27   26                                                            
CONECT   28   16   13   29                                                  
CONECT   29   28   30   32                                                  
CONECT   30   29   31   38                                                  
CONECT   31   30   32                                                       
CONECT   32   31   29   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   30   39   48                                                  
CONECT   39   38   40                                                       
CONECT   40   39   41   42                                                  
CONECT   41   40                                                            
CONECT   42   40   43   47                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   42                                                       
CONECT   48   38   13   49                                                  
CONECT   49   48                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  108    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4R,5R,7S,8S,9S,10S,11R,12R,14S,15S)-2,8,12-Tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0,.0,.0,]octadecan-15-yl benzoic acid	Generator

Chemical Formula

C₃₆H₄₄O₁₃

Average Mass

684.7350 Da

Monoisotopic Mass

684.27819 Da

IUPAC Name

(1R,2S,3S,4R,5R,7S,8S,9S,10S,11R,12R,14S,15S)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0^{1,10}.0^{3,7}.0^{11,14}]octadecan-15-yl benzoate

Traditional Name

(1R,2S,3S,4R,5R,7S,8S,9S,10S,11R,12R,14S,15S)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0^{1,10}.0^{3,7}.0^{11,14}]octadecan-15-yl benzoate

CAS Registry Number

Not Available

SMILES

CCC(=O)O[C@@H]1[C@H](C)C[C@]2(O)[C@@H]1[C@H](OC(C)=O)[C@]13CO[C@@](C)([C@H]1[C@H]1[C@H](C[C@@]1(C)OC(C)=O)[C@H](OC(=O)C1=CC=CC=C1)C3=O)[C@H]2OC(C)=O

InChI Identifier

InChI=1S/C36H44O13/c1-8-23(40)47-26-17(2)14-36(43)25(26)30(45-18(3)37)35-16-44-34(7,32(36)46-19(4)38)28(35)24-22(15-33(24,6)49-20(5)39)27(29(35)41)48-31(42)21-12-10-9-11-13-21/h9-13,17,22,24-28,30,32,43H,8,14-16H2,1-7H3/t17-,22+,24-,25+,26-,27+,28-,30+,32-,33-,34+,35-,36+/m1/s1

InChI Key

OBGLBABTPRECCH-ADUXVFRQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Euphorbia prolifera	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
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Tetrahydrofuran
Tertiary alcohol
Cyclic alcohol
Ketone
Carboxylic acid ester
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.45	ChemAxon
pKa (Strongest Acidic)	13.34	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	178.03 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	166.12 m³·mol⁻¹	ChemAxon
Polarizability	69.66 Å³	ChemAxon
Number of Rings	6	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

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

162985451

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate (NP0254929)

MOL for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

3D MOL for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

3D SDF for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

3D-SDF for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

PDB for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

3D PDB for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

SMILES for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

INCHI for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

Structure for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)

3D Structure for NP0254929 ((1r,2s,3s,4r,5r,7s,8s,9s,10s,11r,12r,14s,15s)-2,8,12-tris(acetyloxy)-7-hydroxy-5,9,12-trimethyl-16-oxo-4-(propanoyloxy)-18-oxapentacyclo[7.7.2.0¹,¹⁰.0³,⁷.0¹¹,¹⁴]octadecan-15-yl benzoate)