NP-MRD: Showing NP-Card for methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate (NP0308017)

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Record Information

Version

2.0

Created at

2022-09-11 01:31:56 UTC

Updated at

2022-09-11 01:31:56 UTC

NP-MRD ID

NP0308017

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate

Description

28-Deoxonimbolide 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. methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate is found in Azadirachta indica and Owenia cepiodora. methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate was first documented in 2010 (PMID: 21116775). Based on a literature review a small amount of articles have been published on 28-Deoxonimbolide (PMID: 24634075) (PMID: 21381696) (PMID: 25381190) (PMID: 24674886).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112203312D          

 33 38  0  0  1  0            999 V2000
    2.4004    4.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0075    3.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273    3.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    2.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343    2.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541    1.7720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8612    1.2134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1246    1.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    1.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016    1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242    2.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115    1.4159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7688    1.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9491    2.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7704    2.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978    1.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788    1.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8313    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099    0.5335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3909   -0.0119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6809    0.4083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8936    0.1619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5499   -0.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304   -0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    0.3158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8950   -0.1619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8577    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666    1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    1.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    2.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668    1.5256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5326    2.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.7205    0.0000 C   0  0  1  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 21 20  1  6  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 22  1  1  0  0  0
 25 33  1  0  0  0  0
M  END

     RDKit          3D

 65 70  0  0  0  0  0  0  0  0999 V2000
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   -0.6719    3.9144   -0.9516 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3372    3.2864    0.1284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085    3.6853    0.3084 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7057    0.8521    0.5298 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0769    0.0999    1.5344 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2462    0.9384    2.8223 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5057   -0.1085    1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5251    0.3256    0.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6047    1.5368   -0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6555   -0.6293    0.5465 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5268   -0.7030   -0.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8719   -0.4564   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2932   -0.6431   -1.9546 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2503   -0.9763   -2.6456 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1587   -1.0293   -1.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9646   -1.9237    0.8592 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8447   -1.4189    1.7523 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6699   -2.1275    1.5062 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2920   -1.2411    1.9786 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6878   -1.7236    1.6206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7372   -3.1018    1.4420 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2242   -3.3842    0.1606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9076   -2.0807   -0.3022 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2677   -2.1309    0.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9008   -1.8877   -1.7420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6394   -0.6734   -2.1951 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2519    4.6640   -2.8228 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4205    2.5763    0.9365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1318    0.7738   -0.4444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6837    1.0350    3.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8798    0.2436    3.4690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8621    1.8160    2.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9034    1.5268   -1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6245    2.4868    0.0662 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6174    1.5247   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2374   -0.3243    1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5419   -0.1703    0.1611 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3227   -0.5172   -2.2799 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1892   -1.2907   -2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6712   -2.5775    1.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5570   -2.4304   -0.0157 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1107   -1.3115    2.7989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2403   -1.3610    3.0964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3766   -1.3514    2.3896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9407   -4.2169    0.1735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4226   -3.6142   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2690   -2.3020    1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9694   -1.3469   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7390   -3.0831   -0.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1004   -2.7046   -2.3978 H   0  0  0  0  0  0  0  0  0  0  0  0
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 31 33  1  0
 31  6  1  0
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 14 13  1  0
 33 22  1  0
  9 19  1  0
 33 25  1  0
  1 34  1  0
  1 35  1  0
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  5 37  1  0
  5 38  1  0
  6 39  1  6
  8 40  1  0
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  8 42  1  0
 21 53  1  1
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 11 45  1  0
 17 49  1  0
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 22 54  1  1
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 32 63  1  0
 32 64  1  0
 33 65  1  6
M  END


  Mrv1652309112203312D          

 33 38  0  0  1  0            999 V2000
    2.4004    4.4994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0075    3.9408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8273    3.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0399    2.8893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4343    2.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2541    1.7720    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8612    1.2134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.1246    1.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6825    1.2908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3016    1.8361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2242    2.6575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0115    1.4159    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7688    1.7433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9491    2.5484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7704    2.6257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0978    1.8685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4788    1.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8313    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0099    0.5335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.6809    0.4083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8936    0.1619    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5499   -0.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7304   -0.4930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676    0.3158    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    0.8577    0.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666    1.5610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    1.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    2.7904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4668    1.5256    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5326    2.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    0.7205    0.0000 C   0  0  1  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  2  0  0  0  0
  3  5  1  0  0  0  0
  6  5  1  1  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
  9 19  1  0  0  0  0
 19 20  1  6  0  0  0
 21 20  1  6  0  0  0
  7 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  1  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
  6 31  1  0  0  0  0
 31 32  1  1  0  0  0
 31 33  1  0  0  0  0
 33 22  1  1  0  0  0
 25 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0308017

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@@H]2OC[C@]3(C)C=CC(=O)[C@@]1(C)[C@@H]23

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O6/c1-14-16(15-7-9-31-12-15)10-17-21(14)27(4)18(11-20(29)30-5)26(3)19(28)6-8-25(2)13-32-22(23(25)26)24(27)33-17/h6-9,12,16-18,22-24H,10-11,13H2,1-5H3/t16-,17+,18-,22-,23+,24-,25+,26+,27-/m1/s1

> <INCHI_KEY>
CWGBIWRWBCYASK-FDRNEMFGSA-N

> <FORMULA>
C27H32O6

> <MOLECULAR_WEIGHT>
452.547

> <EXACT_MASS>
452.21988875

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.19638505693547

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-[(1R,2S,4S,6R,9R,10S,11R,15R,18S)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadeca-7,13-dien-10-yl]acetate

> <JCHEM_LOGP>
3.168734888666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8371868126406907

> <JCHEM_POLAR_SURFACE_AREA>
74.97

> <JCHEM_REFRACTIVITY>
121.90449999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl [(1R,2S,4S,6R,9R,10S,11R,15R,18S)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadeca-7,13-dien-10-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       4.481   8.399   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.614   7.356   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.278   5.853   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.808   5.393   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.411   4.811   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.074   3.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.208   2.265   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.699   3.724   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.741   2.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.896   3.427   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.752   4.961   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.222   2.643   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.635   3.254   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.972   4.757   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.505   4.901   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.116   3.488   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      13.960   2.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.885   1.140   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.352   0.996   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.196  -0.022   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.871   0.762   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.401   0.302   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       4.760  -1.098   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       3.230  -0.920   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.926   0.589   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.671  -0.302   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.601   1.374   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.618   2.914   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.960   3.669   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.921   5.209   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.605   2.848   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.728   4.383   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.268   1.345   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   31                                                  
CONECT    7    6    8    9   21                                             
CONECT    8    7                                                            
CONECT    9    7   10   19                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13                                                       
CONECT   18   12   19                                                       
CONECT   19   18    9   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20    7   22                                                  
CONECT   22   21   23   33                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27   33                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29    6   32   33                                             
CONECT   32   31                                                            
CONECT   33   31   22   25                                                  
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₂O₆

Average Mass

452.5470 Da

Monoisotopic Mass

452.21989 Da

IUPAC Name

methyl 2-[(1R,2S,4S,6R,9R,10S,11R,15R,18S)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadeca-7,13-dien-10-yl]acetate

Traditional Name

methyl [(1R,2S,4S,6R,9R,10S,11R,15R,18S)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0^{2,9}.0^{4,8}.0^{15,18}]octadeca-7,13-dien-10-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H]1[C@@]2(C)[C@H](O[C@H]3C[C@H](C(C)=C23)C2=COC=C2)[C@@H]2OC[C@]3(C)C=CC(=O)[C@@]1(C)[C@@H]23

InChI Identifier

InChI=1S/C27H32O6/c1-14-16(15-7-9-31-12-15)10-17-21(14)27(4)18(11-20(29)30-5)26(3)19(28)6-8-25(2)13-32-22(23(25)26)24(27)33-17/h6-9,12,16-18,22-24H,10-11,13H2,1-5H3/t16-,17+,18-,22-,23+,24-,25+,26+,27-/m1/s1

InChI Key

CWGBIWRWBCYASK-FDRNEMFGSA-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
Owenia cepiodora	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
Naphthofuran
Cyclohexenone
Heteroaromatic compound
Methyl ester
Tetrahydrofuran
Furan
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	3.17	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.97 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	121.9 m³·mol⁻¹	ChemAxon
Polarizability	48.2 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00040807

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

101936072

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Takagi M, Tachi Y, Zhang J, Shinozaki T, Ishii K, Kikuchi T, Ukiya M, Banno N, Tokuda H, Akihisa T: Cytotoxic and melanogenesis-inhibitory activities of limonoids from the leaves of Azadirachta indica (Neem). Chem Biodivers. 2014 Mar;11(3):451-68. doi: 10.1002/cbdv.201300348. [PubMed:24634075 ]
Kikuchi T, Ishii K, Noto T, Takahashi A, Tabata K, Suzuki T, Akihisa T: Cytotoxic and apoptosis-inducing activities of limonoids from the seeds of Azadirachta indica (neem). J Nat Prod. 2011 Apr 25;74(4):866-70. doi: 10.1021/np100783k. Epub 2011 Mar 7. [PubMed:21381696 ]
Liu L, Zhao YL, Cheng GG, Chen YY, Qin XJ, Song CW, Yang XW, Liu YP, Luo XD: Limonoid and Steroidal Saponin from Azadirachta indica. Nat Prod Bioprospect. 2014 Dec;4(6):335-40. doi: 10.1007/s13659-014-0042-2. Epub 2014 Nov 8. [PubMed:25381190 ]
Wu Q, Kohli M, Bergen HR 3rd, Cheville JC, Karnes RJ, Cao H, Young CY, Tindall DJ, McNiven MA, Donkena KV: Preclinical evaluation of the supercritical extract of azadirachta indica (neem) leaves in vitro and in vivo on inhibition of prostate cancer tumor growth. Mol Cancer Ther. 2014 May;13(5):1067-77. doi: 10.1158/1535-7163.MCT-13-0699. Epub 2014 Mar 27. [PubMed:24674886 ]
Zhao FW, Luo M, Wang YH, Li ML, Tang GH, Long CL: A piperidine alkaloid and limonoids from Arisaema decipiens, a traditional antitumor herb used by the Dong people. Arch Pharm Res. 2010 Nov;33(11):1735-9. doi: 10.1007/s12272-010-1104-6. Epub 2010 Nov 30. [PubMed:21116775 ]
LOTUS database [Link]

Showing NP-Card for methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate (NP0308017)

MOL for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

3D MOL for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

3D SDF for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

3D-SDF for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

PDB for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

3D PDB for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

SMILES for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

INCHI for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

Structure for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)

3D Structure for NP0308017 (methyl 2-[(1r,2s,4s,6r,9r,10s,11r,15r,18s)-6-(furan-3-yl)-7,9,11,15-tetramethyl-12-oxo-3,17-dioxapentacyclo[9.6.1.0²,⁹.0⁴,⁸.0¹⁵,¹⁸]octadeca-7,13-dien-10-yl]acetate)