NP-MRD: Showing NP-Card for methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate (NP0326640)

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Record Information

Version

2.0

Created at

2022-09-12 08:23:50 UTC

Updated at

2022-09-12 08:23:50 UTC

NP-MRD ID

NP0326640

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate

Description

Methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-10-en-18-yl]acetate belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate is found in Xylocarpus moluccensis. Methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]Octadec-10-en-18-yl]acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231523052D          

 40 45  0  0  0  0            999 V2000
   -3.5248    0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    1.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1163    0.6815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2556   -0.1317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3425    0.9675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7079    0.4403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6290   -0.3926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4184   -0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2100    0.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3706   -0.2012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1867   -0.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3729    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3341    1.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2466    0.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5406    1.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3552    1.4432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8757    0.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1697    1.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6903    0.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2109    0.2939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4374   -1.1169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1023   -0.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672   -0.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571   -0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9508   -1.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366   -1.7873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5070   -2.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -1.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5459   -1.9222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616   -2.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590   -2.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979   -3.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843    1.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335    2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0513    3.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221    2.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807    1.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 19 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 36 40  1  0  0  0  0
M  END

     RDKit          3D

 76 81  0  0  0  0  0  0  0  0999 V2000
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   -3.4720   -3.1464    1.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1705   -2.1277   -0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8691   -0.8627    0.0647 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8291   -0.8610    1.1286 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7687   -2.0824    1.9942 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614   -0.5448    0.7226 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2940   -1.5662   -0.0721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824   -1.1770    0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0173    0.1134   -0.6697 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2297   -0.2600   -2.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8702    1.0531   -0.5267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7585    0.7778    0.0821 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1847    3.3597   -1.0247 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3528   -0.3749    0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.3111    0.3300    1.9699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6895    0.4652    3.1550 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691    2.3980   -1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979    2.5959   -1.5229 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7656    3.3442   -2.4882 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5040    1.9925   -0.8297 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2562    0.7747   -0.1222 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4326   -0.1086   -0.1642 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2196   -0.4055   -1.2649 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2019   -1.2738   -0.8233 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0258   -1.4900    0.4551 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9837   -0.8157    0.8870 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3518   -6.0654   -0.8405 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5588   -1.8859   -1.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.5173   -2.1549    2.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7579   -2.9926    1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.0759   -0.8603    2.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
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  6 26  1  0
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 37 74  1  0
M  END


  Mrv1533004231523052D          

 40 45  0  0  0  0            999 V2000
   -3.5248    0.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509    1.2087    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4184   -0.6324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1867   -0.0803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.1023   -0.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817    0.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672   -0.0985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4571   -0.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9508   -1.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6071   -0.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7366   -1.7873    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5070   -2.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -1.1689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5459   -1.9222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0616   -2.5901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7590   -2.5046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3979   -3.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9843    1.7048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5335    2.3957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0513    3.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8221    2.7440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807    1.9200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 17 24  1  0  0  0  0
 24 25  2  0  0  0  0
 14 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 10 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  1  0  0  0  0
  7 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 19 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  2  0  0  0  0
 36 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0326640

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC1C2(C)CC3(O)C1(C)C1CCC4(C)C(OC(=O)CC4=C1C(=O)C3(OC)C2OC(C)=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O10/c1-15(31)39-25-27(3)14-29(35)28(4,19(27)12-20(32)36-5)17-7-9-26(2)18(22(17)23(34)30(25,29)37-6)11-21(33)40-24(26)16-8-10-38-13-16/h8,10,13,17,19,24-25,35H,7,9,11-12,14H2,1-6H3

> <INCHI_KEY>
DXAWUJPEJQPCGT-UHFFFAOYSA-N

> <FORMULA>
C30H36O10

> <MOLECULAR_WEIGHT>
556.608

> <EXACT_MASS>
556.230847359

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
55.99081621892839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate

> <ALOGPS_LOGP>
2.71

> <JCHEM_LOGP>
1.9053032243333314

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.032289801054016

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8698095051268915

> <JCHEM_POLAR_SURFACE_AREA>
138.57

> <JCHEM_REFRACTIVITY>
137.33149999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      -6.580   1.722   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.135   2.256   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -3.950   1.272   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.210  -0.246   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.506   1.806   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.321   0.822   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.174  -0.733   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.648  -1.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.392   0.805   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.692  -0.376   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.215  -0.150   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.696   1.004   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.624   2.542   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.327   1.011   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.876   2.450   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.396   2.694   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.368   1.499   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.917   2.938   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.889   1.743   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       7.860   0.549   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.311  -0.890   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       8.283  -2.085   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.791  -1.134   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.819   0.060   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.299  -0.184   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.720  -1.689   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.642  -2.923   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.133  -1.815   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.375  -3.336   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.813  -3.887   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.391  -2.182   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -1.019  -3.588   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.115  -4.835   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.417  -4.675   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.743  -6.241   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.437   3.182   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.596   4.472   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       7.562   5.671   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.001   5.122   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       8.924   3.584   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   12                                                  
CONECT    7    6    8    9   31                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10    6   13   14                                             
CONECT   13   12                                                            
CONECT   14   12   15   25                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   24                                             
CONECT   18   17                                                            
CONECT   19   17   20   36                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   17   25                                                  
CONECT   25   24   14   26                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   10   29   31                                             
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28    7   32                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   19   37   40                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   36                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0,.0,.0,]octadec-10-en-18-yl]acetic acid	Generator
Methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetic acid	Generator

Chemical Formula

C₃₀H₃₆O₁₀

Average Mass

556.6080 Da

Monoisotopic Mass

556.23085 Da

IUPAC Name

methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate

Traditional Name

methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate

CAS Registry Number

Not Available

SMILES

COC(=O)CC1C2(C)CC3(O)C1(C)C1CCC4(C)C(OC(=O)CC4=C1C(=O)C3(OC)C2OC(C)=O)C1=COC=C1

InChI Identifier

InChI=1S/C30H36O10/c1-15(31)39-25-27(3)14-29(35)28(4,19(27)12-20(32)36-5)17-7-9-26(2)18(22(17)23(34)30(25,29)37-6)11-21(33)40-24(26)16-8-10-38-13-16/h8,10,13,17,19,24-25,35H,7,9,11-12,14H2,1-6H3

InChI Key

DXAWUJPEJQPCGT-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Xylocarpus moluccensis	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

Mexicanolide
Limonoid skeleton
Prostaglandin skeleton
Steroid lactone
Eicosanoid
2-oxosteroid
Oxosteroid
11-oxosteroid
Steroid
3-oxasteroid
Naphthopyran
Naphthalene
Tricarboxylic acid or derivatives
Delta valerolactone
Delta_valerolactone
Fatty acyl
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Methyl ester
Tertiary alcohol
Lactone
Ketone
Carboxylic acid ester
Ether
Dialkyl ether
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
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	2.71	ALOGPS
logP	1.91	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	138.57 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.33 m³·mol⁻¹	ChemAxon
Polarizability	55.99 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate (NP0326640)

MOL for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D MOL for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D SDF for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D-SDF for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

PDB for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D PDB for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

SMILES for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

INCHI for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

Structure for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)

3D Structure for NP0326640 (methyl 2-[14-(acetyloxy)-6-(furan-3-yl)-17-hydroxy-13-methoxy-1,5,15-trimethyl-8,12-dioxo-7-oxapentacyclo[13.2.1.0²,¹¹.0⁵,¹⁰.0¹³,¹⁷]octadec-10-en-18-yl]acetate)