NP-MRD: Showing NP-Card for 4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate (NP0224967)

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Record Information

Version

2.0

Created at

2022-09-06 03:33:14 UTC

Updated at

2022-09-06 03:33:14 UTC

NP-MRD ID

NP0224967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate

Description

9-(Acetyloxy)-14-(2,5-dioxo-2,5-dihydrofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-16-yl acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate is found in Azadirachta indica. 9-(Acetyloxy)-14-(2,5-dioxo-2,5-dihydrofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadeca-3,11-dien-16-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171512332D          

 41 45  0  0  0  0            999 V2000
    6.5807   -3.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883   -4.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -0.1885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0140    0.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822    1.2181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261    0.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -3.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -3.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -4.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1084   -4.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -3.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -4.2136    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 34  1  0  0  0  0
 15 34  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END


  Mrv1533004171512332D          

 41 45  0  0  0  0            999 V2000
    6.5807   -3.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7686   -3.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2368   -3.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247   -3.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1444   -3.9229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6762   -4.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4883   -4.4084    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959   -5.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0683   -2.4895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8390   -1.6970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5218   -1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -1.7404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9853   -1.5952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534   -0.9645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2655   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7337   -0.1885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0140    0.5874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4822    1.2181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261    0.7326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3580    0.1019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4216   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1376   -0.3850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1351   -0.7453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9534   -1.7902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7655   -1.6450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6731   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8610   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0489   -2.8566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5171   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7373   -3.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -3.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6646   -4.1193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1084   -4.3963    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7912   -3.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5671   -4.2136    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  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
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
  3 34  1  0  0  0  0
 15 34  1  0  0  0  0
 11 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 39 40  1  0  0  0  0
 35 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0224967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(OC(C)=O)C2(C)C(CC=C2C2(C)C(OC(C)=O)C(O)C3C(C)(C)C(=O)C=CC3(C)C12)C1=CC(=O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O10/c1-14(32)39-25-21(36)23-28(3,4)19(34)11-12-29(23,5)24-22(38-8)26(40-15(2)33)30(6)17(9-10-18(30)31(24,25)7)16-13-20(35)41-27(16)37/h10-13,17,21-26,36H,9H2,1-8H3

> <INCHI_KEY>
JSXJRQVDHPCREN-UHFFFAOYSA-N

> <FORMULA>
C31H38O10

> <MOLECULAR_WEIGHT>
570.635

> <EXACT_MASS>
570.246497424

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
79

> <JCHEM_AVERAGE_POLARIZABILITY>
58.15883015799515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(acetyloxy)-14-(2,5-dioxo-2,5-dihydrofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-16-yl acetate

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.592846543333332

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.712114322013068

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.778359592750135

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3055405140196408

> <JCHEM_POLAR_SURFACE_AREA>
142.5

> <JCHEM_REFRACTIVITY>
145.53880000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.25e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(acetyloxy)-14-(2,5-dioxofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-16-yl acetate

> <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      12.284  -6.510   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.768  -6.781   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.736  -7.323   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       8.729  -8.500   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      10.245  -8.229   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.206  -9.949   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.313  -1.800   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.836  -0.352   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.360   1.096   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.367   2.274   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      10.875   1.368   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.243  -5.813   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.720  -7.261   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.241  -7.689   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       3.936  -8.206   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       5.210  -7.342   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.659  -7.865   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   34                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11   14                                             
CONECT   10    9                                                            
CONECT   11    9   12   35                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16   17   34                                             
CONECT   16   15                                                            
CONECT   17   15   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   24   33   34                                             
CONECT   33   32                                                            
CONECT   34   32    3   15                                                  
CONECT   35   11   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   35   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Value	Source
9-(Acetyloxy)-14-(2,5-dioxo-2,5-dihydrofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0,.0,]heptadeca-3,11-dien-16-yl acetic acid	Generator
9-(Acetyloxy)-14-(2,5-dioxo-2,5-dihydrofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-16-yl acetic acid	Generator

Chemical Formula

C₃₁H₃₈O₁₀

Average Mass

570.6350 Da

Monoisotopic Mass

570.24650 Da

IUPAC Name

9-(acetyloxy)-14-(2,5-dioxo-2,5-dihydrofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-16-yl acetate

Traditional Name

9-(acetyloxy)-14-(2,5-dioxofuran-3-yl)-8-hydroxy-17-methoxy-2,6,6,10,15-pentamethyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,11-dien-16-yl acetate

CAS Registry Number

Not Available

SMILES

COC1C(OC(C)=O)C2(C)C(CC=C2C2(C)C(OC(C)=O)C(O)C3C(C)(C)C(=O)C=CC3(C)C12)C1=CC(=O)OC1=O

InChI Identifier

InChI=1S/C31H38O10/c1-14(32)39-25-21(36)23-28(3,4)19(34)11-12-29(23,5)24-22(38-8)26(40-15(2)33)30(6)17(9-10-18(30)31(24,25)7)16-13-20(35)41-27(16)37/h10-13,17,21-26,36H,9H2,1-8H3

InChI Key

JSXJRQVDHPCREN-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
Steroid ester
3-oxo-delta-1-steroid
3-oxosteroid
6-hydroxysteroid
Hydroxysteroid
Oxosteroid
Delta-1-steroid
Steroid
Tetracarboxylic acid or derivatives
Cyclohexenone
2-furanone
Carboxylic acid anhydride
Cyclic alcohol
Dihydrofuran
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid derivative
Ether
Dialkyl ether
Organic oxide
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	2.63	ALOGPS
logP	2.59	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	13.78	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	142.5 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.54 m³·mol⁻¹	ChemAxon
Polarizability	58.16 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate (NP0224967)

MOL for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D MOL for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D SDF for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D-SDF for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

PDB for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D PDB for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

SMILES for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

INCHI for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

Structure for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)

3D Structure for NP0224967 (4-(acetyloxy)-1-(2,5-dioxofuran-3-yl)-5-hydroxy-10-methoxy-3b,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,4h,5h,5ah,9bh,10h,11h-cyclopenta[a]phenanthren-11-yl acetate)