NP-MRD: Showing NP-Card for 8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate (NP0224608)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-06 03:05:04 UTC

Updated at

2022-09-06 03:05:05 UTC

NP-MRD ID

NP0224608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate

Description

8-(Acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylpropanoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate is found in Ajuga bracteosa, Ajuga iva and Ajuga reptans. 8-(Acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylpropanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171513312D          

 38 42  0  0  0  0            999 V2000
   -7.6819    1.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0499    2.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1931    3.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746    2.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6426    2.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1314    1.3938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3561    1.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241    1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8674    2.4544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    1.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056    0.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8871    1.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8871   -0.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1119   -0.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -1.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2944   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9263   -1.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7831   -2.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078   -2.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4151   -2.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4376    0.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6372   -0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4302   -1.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6298   -1.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446   -2.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4229   -2.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2129    0.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950   -0.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0253    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054    0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205    0.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358    0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512    0.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512   -0.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358   -0.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205   -0.4023    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
M  END


  Mrv1533004171513312D          

 38 42  0  0  0  0            999 V2000
   -7.6819    1.9581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0499    2.4884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1931    3.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2746    2.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6426    2.7366    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1314    1.3938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3561    1.1116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7241    1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8674    2.4544    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    1.3598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8056    0.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0304    0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8871    1.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8871   -0.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1119   -0.8295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5191   -1.0776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2944   -0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9263   -1.3258    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7831   -2.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0078   -2.4204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4151   -2.6685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4376    0.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6372   -0.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4302   -1.0109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6298   -1.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7446   -2.6284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4229   -2.0388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2129    0.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4950   -0.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0253    0.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2054    0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205    0.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358    0.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512    0.9326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3337    0.2651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1512   -0.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9358   -0.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7205   -0.4023    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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 11 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 22 28  1  0  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
 12 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  1  0  0  0  0
 37 38  1  0  0  0  0
 31 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)OC1C(O)CC2C(C)(C3CC4CCOC4O3)C(C)CC(OC(C)=O)C2(COC(C)=O)C11CO1

> <INCHI_IDENTIFIER>
InChI=1S/C28H42O10/c1-14(2)24(32)38-23-19(31)11-20-26(6,21-10-18-7-8-33-25(18)37-21)15(3)9-22(36-17(5)30)27(20,12-34-16(4)29)28(23)13-35-28/h14-15,18-23,25,31H,7-13H2,1-6H3

> <INCHI_KEY>
GDRNWAABIDILBN-UHFFFAOYSA-N

> <FORMULA>
C28H42O10

> <MOLECULAR_WEIGHT>
538.634

> <EXACT_MASS>
538.277797552

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
56.55385041565465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylpropanoate

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
1.7949738243333333

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.066834883248617

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2069664220670546

> <JCHEM_POLAR_SURFACE_AREA>
130.12000000000003

> <JCHEM_REFRACTIVITY>
131.3202

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0     -14.339   3.655   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.160   4.645   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -13.427   6.162   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -11.713   4.118   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0     -10.533   5.108   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0     -11.445   2.602   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -9.998   2.075   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.818   3.065   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -9.086   4.582   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -7.371   2.538   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.104   1.022   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.657   0.495   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -5.389   2.012   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.389  -1.022   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.942  -1.548   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.569  -2.012   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -8.016  -1.485   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -9.196  -2.475   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -8.928  -3.991   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.481  -4.518   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -10.108  -4.981   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.284   0.032   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.656  -1.463   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.136  -1.887   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0     -10.509  -3.381   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0     -10.723  -4.906   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0     -11.989  -3.806   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -9.731   0.558   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -10.257  -0.889   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0     -11.247   0.291   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -4.117   0.495   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.212   1.741   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.747   1.265   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.282   1.741   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       0.623   0.495   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -0.282  -0.751   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      -1.747  -0.275   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.212  -0.751   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   28                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   22                                                  
CONECT   12   11   13   14   31                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   11   23   28                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   22    7   29   30                                             
CONECT   29   28   30                                                       
CONECT   30   29   28                                                       
CONECT   31   12   32   38                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   33   38                                                  
CONECT   38   37   31                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
8-(Acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₈H₄₂O₁₀

Average Mass

538.6340 Da

Monoisotopic Mass

538.27780 Da

IUPAC Name

8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-octahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylpropanoate

Traditional Name

8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2H-spiro[naphthalene-1,2'-oxirane]-2-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)OC1C(O)CC2C(C)(C3CC4CCOC4O3)C(C)CC(OC(C)=O)C2(COC(C)=O)C11CO1

InChI Identifier

InChI=1S/C28H42O10/c1-14(2)24(32)38-23-19(31)11-20-26(6,21-10-18-7-8-33-25(18)37-21)15(3)9-22(36-17(5)30)27(20,12-34-16(4)29)28(23)13-35-28/h14-15,18-23,25,31H,7-13H2,1-6H3

InChI Key

GDRNWAABIDILBN-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ajuga bracteosa	LOTUS Database	35616633
Ajuga iva	LOTUS Database	35616633
Ajuga reptans	LOTUS Database	35616633

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Furofuran
Cyclic alcohol
Tetrahydrofuran
Carboxylic acid ester
Secondary alcohol
Oxacycle
Acetal
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.41	ALOGPS
logP	1.79	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14.07	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	130.12 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	131.32 m³·mol⁻¹	ChemAxon
Polarizability	56.55 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	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

53462657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate (NP0224608)

MOL for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

3D MOL for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

3D SDF for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

3D-SDF for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

PDB for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

3D PDB for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

SMILES for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

INCHI for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

Structure for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)

3D Structure for NP0224608 (8-(acetyloxy)-8a-[(acetyloxy)methyl]-5-{hexahydrofuro[2,3-b]furan-2-yl}-3-hydroxy-5,6-dimethyl-hexahydro-2h-spiro[naphthalene-1,2'-oxiran]-2-yl 2-methylpropanoate)