NP-MRD: Showing NP-Card for (1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate (NP0244735)

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Record Information

Version

1.0

Created at

2022-09-07 05:36:15 UTC

Updated at

2022-09-07 05:36:15 UTC

NP-MRD ID

NP0244735

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309072207362D          

 45 50  0  0  1  0            999 V2000
   -1.3114   -0.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652   -0.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966    0.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126   -1.0446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588   -0.6929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9274    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736    0.4810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7422    1.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644    1.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    1.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330    2.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3514    0.0105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5343    0.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828   -0.8116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8479   -1.4127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4509   -2.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -1.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -1.1633    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8311   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6510   -1.2238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2162   -1.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782   -2.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433   -3.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1751   -2.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -3.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340   -3.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -4.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.4339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4076   -1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113   -0.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202   -1.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941   -1.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950   -0.7327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6797   -1.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4545   -0.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635   -1.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5032   -2.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7098   -2.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649    0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715    0.3179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9232    1.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    2.2232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4415    0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.1672    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  6  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  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 38  2  0  0  0  0
 33 39  1  0  0  0  0
 40 39  1  1  0  0  0
 30 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 45 44  1  1  0  0  0
 28 45  1  0  0  0  0
 12 45  1  0  0  0  0
M  END


  Mrv1652309072207362D          

 45 50  0  0  1  0            999 V2000
   -1.3114   -0.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652   -0.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966    0.2480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126   -1.0446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8588   -0.6929    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9274    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6736    0.4810    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7422    1.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644    1.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3182    1.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1330    2.5957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3514    0.0105    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5343    0.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828   -0.8116    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8479   -1.4127    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.4509   -2.1359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6405   -1.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5366   -1.1633    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8311   -1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6510   -1.2238    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2162   -1.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782   -2.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5433   -3.2158    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1751   -2.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9371   -3.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1340   -3.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5022   -4.1946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -0.4339    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4076   -1.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7113   -0.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2202   -1.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9941   -1.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9950   -0.7327    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.6797   -1.1929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4545   -0.9095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9635   -1.5588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5032   -2.2435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7098   -2.0174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9649    0.0918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1715    0.3179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9232    1.1046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1532    1.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0862    2.2232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4415    0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3239    0.1672    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  6  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  1  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 14 18  1  0  0  0  0
 18 19  1  1  0  0  0
 15 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  1  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 34 38  2  0  0  0  0
 33 39  1  0  0  0  0
 40 39  1  1  0  0  0
 30 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
 45 44  1  1  0  0  0
 28 45  1  0  0  0  0
 12 45  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244735

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

> <INCHI_IDENTIFIER>
InChI=1S/C35H44O10/c1-17(2)11-27(38)45-32-30-31-33(6,16-41-30)25(42-19(4)36)14-26(43-20(5)37)34(31,7)24-13-28(39)44-23-12-22(21-9-10-40-15-21)18(3)29(23)35(24,32)8/h9-11,15,22-26,30-32H,12-14,16H2,1-8H3/t22-,23+,24-,25+,26+,30-,31+,32-,33-,34+,35-/m1/s1

> <INCHI_KEY>
IHZVQPJZVJIUHE-DHBUHNJJSA-N

> <FORMULA>
C35H44O10

> <MOLECULAR_WEIGHT>
624.727

> <EXACT_MASS>
624.293447617

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
66.13195548508656

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
3.603650954333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8571261070974505

> <JCHEM_POLAR_SURFACE_AREA>
127.57

> <JCHEM_REFRACTIVITY>
160.4119

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.448  -1.728   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.055  -1.072   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.927   0.463   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.210  -1.950   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.603  -1.293   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.731   0.241   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.124   0.898   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.252   2.432   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.987   3.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.594   2.654   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.115   4.845   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.389   0.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.731   1.521   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.261  -1.515   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.316  -2.637   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.575  -3.987   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.062  -3.699   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.868  -2.172   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.551  -2.970   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.815  -2.284   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       7.870  -3.406   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.426  -4.881   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.481  -6.003   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.927  -5.233   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.483  -6.708   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.984  -7.061   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.537  -7.830   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.259  -0.810   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.228  -2.008   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.794  -0.685   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.744  -1.897   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.322  -3.378   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      11.191  -1.368   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      12.469  -2.227   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      13.915  -1.698   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.865  -2.910   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      14.006  -4.188   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      12.525  -3.766   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      11.135   0.171   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       9.654   0.593   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       9.190   2.062   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       7.753   2.615   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       7.627   4.150   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       6.424   1.836   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       6.205   0.312   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   18                                                  
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   45                                             
CONECT   13   12                                                            
CONECT   14   12   15   18                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    5   14   19                                             
CONECT   19   18                                                            
CONECT   20   15   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
CONECT   28   20   29   30   45                                             
CONECT   29   28                                                            
CONECT   30   28   31   40                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   39                                                  
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   34                                                       
CONECT   39   33   40                                                       
CONECT   40   39   30   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   28   12                                                  
MASTER        0    0    0    0    0    0    0    0   45    0  100    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,6S,8R,11R,12S,13R,16R,17S,19S,20R)-17,19-Bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0,.0,.0,]icos-9-en-12-yl 3-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₅H₄₄O₁₀

Average Mass

624.7270 Da

Monoisotopic Mass

624.29345 Da

IUPAC Name

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

Traditional Name

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

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

InChI Identifier

InChI=1S/C35H44O10/c1-17(2)11-27(38)45-32-30-31-33(6,16-41-30)25(42-19(4)36)14-26(43-20(5)37)34(31,7)24-13-28(39)44-23-12-22(21-9-10-40-15-21)18(3)29(23)35(24,32)8/h9-11,15,22-26,30-32H,12-14,16H2,1-8H3/t22-,23+,24-,25+,26+,30-,31+,32-,33-,34+,35-/m1/s1

InChI Key

IHZVQPJZVJIUHE-DHBUHNJJSA-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
Tetracarboxylic acid or derivatives
Caprolactone
Fatty acid ester
Oxepane
Fatty acyl
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Heteroaromatic compound
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
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
logP	3.6	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	127.57 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	160.41 m³·mol⁻¹	ChemAxon
Polarizability	66.13 Å³	ChemAxon
Number of Rings	6	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

163041681

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,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate (NP0244735)

MOL for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

3D MOL for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

3D SDF for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

3D-SDF for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

PDB for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

3D PDB for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

SMILES for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

INCHI for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

Structure for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)

3D Structure for NP0244735 ((1r,2r,6s,8r,11r,12s,13r,16r,17s,19s,20r)-17,19-bis(acetyloxy)-8-(furan-3-yl)-1,9,11,16-tetramethyl-4-oxo-5,14-dioxapentacyclo[11.6.1.0²,¹¹.0⁶,¹⁰.0¹⁶,²⁰]icos-9-en-12-yl 3-methylbut-2-enoate)