NP-MRD: Showing NP-Card for (1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one (NP0332635)

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Record Information

Version

2.0

Created at

2024-03-14 02:52:21 UTC

Updated at

2024-11-01 00:37:58 UTC

NP-MRD ID

NP0332635

Natural Product DOI

https://doi.org/10.57994/1895

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one

Description

(1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one 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. Based on a literature review very few articles have been published on (1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 03142402522D          

 45 49  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  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  2  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  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261    0.7326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  2  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
    7.1701    0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4504    1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1413   -1.9354    0.0000 H   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  2  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  2  0  0  0  0  0  0  0  0  0
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9246   -3.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8322   -4.8939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  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  1  0  0  0  0  0  0  0  0  0
    4.7050   -2.3711    0.0000 H   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
    3.5218   -1.2340    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
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2580   -2.3340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3721   -3.2963    0.0000 H   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
    2.1084   -4.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -3.8899    0.0000 O   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
    2.0816   -5.2209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11  6  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 16 11  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 18  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 29 24  1  0  0  0  0
 29 16  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31  4  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  2  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  0  0  0  0
 37  2  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  6  0  0  0
 39 40  1  1  0  0  0
 39 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 42 45  2  0  0  0  0
M  END


  Mrv2104 03142402522D          

 45 49  0  0  1  0            999 V2000
    3.5330   -3.2587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8928   -2.5163    0.0000 C   0  0  2  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  2  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  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8261    0.7326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0777   -0.6740    0.0000 C   0  0  2  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
    7.1701    0.2471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4504    1.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7019   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6095   -1.3047    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1413   -1.9354    0.0000 H   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  2  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  2  0  0  0  0  0  0  0  0  0
    6.5807   -3.4873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9246   -3.9728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8322   -4.8939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -2.0807    0.0000 C   0  0  1  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  1  0  0  0  0  0  0  0  0  0
    4.7050   -2.3711    0.0000 H   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
    3.5218   -1.2340    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
    3.0683   -2.4895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2580   -2.3340    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5619   -3.1408    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3721   -3.2963    0.0000 H   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
    2.1084   -4.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4570   -3.8899    0.0000 O   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
    2.0816   -5.2209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  4  3  1  0  0  0  0
  4  5  1  1  0  0  0
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 11  6  1  0  0  0  0
 11 12  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 16 11  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 21 18  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 24 23  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 29 24  1  0  0  0  0
 29 16  1  0  0  0  0
 29 30  1  1  0  0  0
 29 31  1  0  0  0  0
 31  4  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 34  1  0  0  0  0
  3 35  2  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  0  0  0  0
 37  2  1  0  0  0  0
 37 38  1  1  0  0  0
 37 39  1  6  0  0  0
 39 40  1  1  0  0  0
 39 41  1  6  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 39 44  1  0  0  0  0
 42 45  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332635

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(COC(=O)C1)[C@]1([H])CC=C2[C@@]1(C)CC[C@@]1([H])[C@@]2(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2([H])C(C)(C)[C@H](O)C[C@H](OC(C)=O)[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O9/c1-16(33)39-24-14-23(36)29(4,5)27-26(40-17(2)34)28(41-18(3)35)31(7)21-10-9-20(19-13-25(37)38-15-19)30(21,6)12-11-22(31)32(24,27)8/h10,19-20,22-24,26-28,36H,9,11-15H2,1-8H3/t19-,20+,22+,23-,24+,26-,27+,28-,30+,31+,32+/m1/s1

> <INCHI_KEY>
RYUSYXIJSFRRFU-XPQKEQNESA-N

> <FORMULA>
C32H46O9

> <MOLECULAR_WEIGHT>
574.711

> <EXACT_MASS>
574.314183061

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
87

> <JCHEM_AVERAGE_POLARIZABILITY>
61.46886027742666

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3bR,4S,5R,5aS,7R,9S,9aR,9bR,11aS)-5,9-bis(acetyloxy)-7-hydroxy-3b,6,6,9a,11a-pentamethyl-1-[(3S)-5-oxooxolan-3-yl]-1H,2H,3bH,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-4-yl acetate

> <JCHEM_LOGP>
2.3126994226666664

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.619792171433

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9651029042152057

> <JCHEM_POLAR_SURFACE_AREA>
125.43

> <JCHEM_REFRACTIVITY>
147.36100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3bR,4S,5R,5aS,7R,9S,9aR,9bR,11aS)-5,9-bis(acetyloxy)-7-hydroxy-3b,6,6,9a,11a-pentamethyl-1-[(3S)-5-oxooxolan-3-yl]-1H,2H,4H,5H,5aH,7H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAR-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAR-24         0                                  
HETATM    1  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.313  -1.800   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       8.836  -0.352   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       9.360   1.096   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.367   2.274   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.875   1.368   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      13.384   0.461   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.907   1.910   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      14.377  -0.716   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0      13.330  -3.613   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.284  -6.510   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.277  -7.687   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.793  -7.416   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      12.753  -9.135   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   32  H   UNK     0       8.783  -4.426   0.000  0.00  0.00           H+0
HETATM   33  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   38  H   UNK     0       4.215  -4.357   0.000  0.00  0.00           H+0
HETATM   39  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   40  H   UNK     0       6.295  -6.153   0.000  0.00  0.00           H+0
HETATM   41  C   UNK     0       5.210  -7.342   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       3.936  -8.206   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.720  -7.261   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       3.243  -5.813   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       3.886  -9.746   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34   37                                             
CONECT    3    2    4   35                                                  
CONECT    4    3    5    6   31                                             
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    6   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   18   29                                             
CONECT   17   16                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   24   16   30   31                                             
CONECT   30   29                                                            
CONECT   31   29    4   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33    2                                                       
CONECT   35    3   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    2   38   39                                             
CONECT   38   37                                                            
CONECT   39   37   40   41   44                                             
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43   45                                                  
CONECT   43   42   44                                                       
CONECT   44   43   39                                                       
CONECT   45   42                                                            
MASTER        0    0    0    0    0    0    0    0   45    0   98    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₄₆O₉

Average Mass

574.7110 Da

Monoisotopic Mass

574.31418 Da

IUPAC Name

(1S,3bR,4S,5R,5aS,7R,9S,9aR,9bR,11aS)-5,9-bis(acetyloxy)-7-hydroxy-3b,6,6,9a,11a-pentamethyl-1-[(3S)-5-oxooxolan-3-yl]-1H,2H,3bH,4H,5H,5aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-4-yl acetate

Traditional Name

(1S,3bR,4S,5R,5aS,7R,9S,9aR,9bR,11aS)-5,9-bis(acetyloxy)-7-hydroxy-3b,6,6,9a,11a-pentamethyl-1-[(3S)-5-oxooxolan-3-yl]-1H,2H,4H,5H,5aH,7H,8H,9H,9bH,10H,11H-cyclopenta[a]phenanthren-4-yl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(COC(=O)C1)[C@]1([H])CC=C2[C@@]1(C)CC[C@@]1([H])[C@@]2(C)[C@H](OC(C)=O)[C@H](OC(C)=O)[C@@]2([H])C(C)(C)[C@H](O)C[C@H](OC(C)=O)[C@]12C

InChI Identifier

InChI=1S/C32H46O9/c1-16(33)39-24-14-23(36)29(4,5)27-26(40-17(2)34)28(41-18(3)35)31(7)21-10-9-20(19-13-25(37)38-15-19)30(21,6)12-11-22(31)32(24,27)8/h10,19-20,22-24,26-28,36H,9,11-15H2,1-8H3/t19-,20+,22+,23-,24+,26-,27+,28-,30+,31+,32+/m1/s1

InChI Key

RYUSYXIJSFRRFU-XPQKEQNESA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Kanazawa University	Kyoko Nakagawa-Goto	2024-03-14	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Kanazawa University	Kyoko Nakagawa-Goto	2024-03-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Kanazawa University	Kyoko Nakagawa-Goto	2024-03-14	View Spectrum
NOESY NMR	[¹H, ¹H] NMR Spectrum (2D, 400 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Kanazawa University	Kyoko Nakagawa-Goto	2024-03-14	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Kanazawa University	Kyoko Nakagawa-Goto	2024-03-14	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Kanazawa University	Kyoko Nakagawa-Goto	2024-03-14	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CDCL3, experimental)	kngoto@p.kanazawa-u.ac.jp	Kanazawa University	Kyoko Nakagawa-Goto	2024-03-14	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
delphinensis		Not Available

Chemical Taxonomy

Description

This compound 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 lactone
Steroid ester
3-alpha-hydroxysteroid
Hydroxysteroid
3-hydroxysteroid
Steroid
Tetracarboxylic acid or derivatives
Fatty alcohol ester
Fatty acid ester
Fatty acyl
Gamma butyrolactone
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	2.31	ChemAxon
pKa (Strongest Acidic)	14.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	125.43 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	147.36 m³·mol⁻¹	ChemAxon
Polarizability	61.47 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

Not Available

Showing NP-Card for (1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one (NP0332635)

MOL for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

3D MOL for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

3D SDF for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

3D-SDF for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

PDB for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

3D PDB for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

SMILES for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

INCHI for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

Structure for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)

3D Structure for NP0332635 ((1S,3R,5S,6R,7S,8R,9R,10R,13S,17S,20S)-1,6,7-triacetoxy-21,23-epoxy-3-hydroxy-24,25,26,27-tetranorapotirucall-14-en-23-one)