NP-MRD: Showing NP-Card for (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate (NP0299798)

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Record Information

Version

2.0

Created at

2022-09-10 11:50:11 UTC

Updated at

2022-09-10 11:50:11 UTC

NP-MRD ID

NP0299798

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate

Description

Nimbolinin A 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. (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate is found in Melia azedarach. Based on a literature review very few articles have been published on Nimbolinin A.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102213502D          

 47 53  0  0  1  0            999 V2000
    0.3182   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -2.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330   -3.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422   -1.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736   -1.1633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9274   -0.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.0105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1126    0.3623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440    1.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    1.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366    0.4810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8311    0.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4509    1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479    0.7303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6510    0.5414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2162    1.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782    1.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1751    2.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433    2.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    3.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704    3.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735    3.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9115    2.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3464    2.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.2485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4076    0.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113   -0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.0503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6797    0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7098    1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5032    1.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635    0.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4545    0.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649   -0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -1.0003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9232   -1.7870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532   -2.0833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0862   -2.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4415   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239   -0.8496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3514   -0.6929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5343   -1.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828    0.1293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  2  0  0  0  0
 32 38  1  0  0  0  0
 39 38  1  6  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 44 43  1  6  0  0  0
 27 44  1  0  0  0  0
 44 45  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 47 16  1  6  0  0  0
 12 47  1  0  0  0  0
M  END


  Mrv1652309102213502D          

 47 53  0  0  1  0            999 V2000
    0.3182   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -2.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330   -3.2780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7422   -1.9855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736   -1.1633    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9274   -0.8116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588    0.0105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1126    0.3623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440    1.1844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    1.6548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7022    1.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366    0.4810    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8311    0.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405    1.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4509    1.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8479    0.7303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6510    0.5414    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2162    1.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782    1.9324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1751    2.1213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433    2.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3053    3.3234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8704    3.9245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6735    3.7356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9115    2.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3464    2.3446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.2485    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4076    0.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113   -0.3156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202    0.3337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941    1.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950    0.0503    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6797    0.5106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7098    1.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5032    1.5611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635    0.8765    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4545    0.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649   -0.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715   -1.0003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9232   -1.7870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532   -2.0833    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0862   -2.9056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4415   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239   -0.8496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3514   -0.6929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5343   -1.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828    0.1293    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 21 26  1  0  0  0  0
 17 27  1  0  0  0  0
 27 28  1  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  6  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 33 37  2  0  0  0  0
 32 38  1  0  0  0  0
 39 38  1  6  0  0  0
 29 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  1  0  0  0
 41 43  1  0  0  0  0
 44 43  1  6  0  0  0
 27 44  1  0  0  0  0
 44 45  1  0  0  0  0
  5 45  1  0  0  0  0
 45 46  1  6  0  0  0
 45 47  1  0  0  0  0
 47 16  1  6  0  0  0
 12 47  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0299798

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H](OC(C)=O)[C@@]2(C)[C@H]3[C@@H](OC[C@]13C)[C@@H](OC(=O)C1=CC=CC=C1)[C@]1(C)[C@@H]2C[C@H](O)O[C@H]2C[C@H](C(C)=C12)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H44O10/c1-19-24(23-12-13-42-17-23)14-25-30(19)37(6)26(15-29(40)46-25)36(5)28(45-21(3)39)16-27(44-20(2)38)35(4)18-43-31(32(35)36)33(37)47-34(41)22-10-8-7-9-11-22/h7-13,17,24-29,31-33,40H,14-16,18H2,1-6H3/t24-,25+,26-,27-,28+,29-,31-,32+,33-,35-,36+,37-/m1/s1

> <INCHI_KEY>
OKUVUCGZOWQVGJ-ONHQIENLSA-N

> <FORMULA>
C37H44O10

> <MOLECULAR_WEIGHT>
648.749

> <EXACT_MASS>
648.293447617

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
67.49399721267048

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl benzoate

> <JCHEM_LOGP>
3.826072974333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.447704150941256

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8439406390624566

> <JCHEM_POLAR_SURFACE_AREA>
130.73

> <JCHEM_REFRACTIVITY>
167.86490000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4R,6S,8R,11R,12S,13R,16R,17R,19S,20R)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0^{2,11}.0^{6,10}.0^{16,20}]icos-9-en-12-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       0.594  -3.928   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.987  -4.584   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.115  -6.119   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.252  -3.706   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.124  -2.172   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.731  -1.515   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.603   0.020   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.210   0.676   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.082   2.211   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.347   3.089   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.311   2.867   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.868   0.898   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.551   1.696   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.062   2.426   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       4.575   2.713   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       5.316   1.363   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.815   1.011   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       7.870   2.133   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       7.426   3.607   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.927   3.960   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       8.481   4.729   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.037   6.204   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.091   7.326   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.591   6.973   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.035   5.499   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.980   4.377   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.259  -0.464   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.228   0.734   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.794  -0.589   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.744   0.623   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.322   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.191   0.094   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.469   0.953   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.525   2.492   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.006   2.914   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      14.865   1.636   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      13.915   0.424   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      11.135  -1.445   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.654  -1.867   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       9.190  -3.336   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       7.753  -3.889   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       7.627  -5.424   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       6.424  -3.110   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       6.205  -1.586   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.389  -1.293   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.731  -2.795   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.261   0.241   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   45                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   14   47                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   47                                                  
CONECT   17   16   18   27                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   17   28   29   44                                             
CONECT   28   27                                                            
CONECT   29   27   30   39                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   38                                                  
CONECT   33   32   34   37                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   33                                                       
CONECT   38   32   39                                                       
CONECT   39   38   29   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   44                                                       
CONECT   44   43   27   45                                                  
CONECT   45   44    5   46   47                                             
CONECT   46   45                                                            
CONECT   47   45   16   12                                                  
MASTER        0    0    0    0    0    0    0    0   47    0  106    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₇H₄₄O₁₀

Average Mass

648.7490 Da

Monoisotopic Mass

648.29345 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H](OC(C)=O)[C@@]2(C)[C@H]3[C@@H](OC[C@]13C)[C@@H](OC(=O)C1=CC=CC=C1)[C@]1(C)[C@@H]2C[C@H](O)O[C@H]2C[C@H](C(C)=C12)C1=COC=C1

InChI Identifier

InChI=1S/C37H44O10/c1-19-24(23-12-13-42-17-23)14-25-30(19)37(6)26(15-29(40)46-25)36(5)28(45-21(3)39)16-27(44-20(2)38)35(4)18-43-31(32(35)36)33(37)47-34(41)22-10-8-7-9-11-22/h7-13,17,24-29,31-33,40H,14-16,18H2,1-6H3/t24-,25+,26-,27-,28+,29-,31-,32+,33-,35-,36+,37-/m1/s1

InChI Key

OKUVUCGZOWQVGJ-ONHQIENLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Melia azedarach	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
Benzoate ester
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Benzoyl
Oxepane
Monocyclic benzene moiety
Benzenoid
Heteroaromatic compound
Tetrahydrofuran
Furan
Carboxylic acid ester
Hemiacetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Dialkyl ether
Ether
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00047791

Chemspider ID

8755461

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10580081

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate (NP0299798)

MOL for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D MOL for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D SDF for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D-SDF for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

PDB for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D PDB for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

SMILES for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

INCHI for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

Structure for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)

3D Structure for NP0299798 ((1r,2r,4r,6s,8r,11r,12s,13r,16r,17r,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-4-hydroxy-1,9,11,16-tetramethyl-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl benzoate)