NP-MRD: Showing NP-Card for trichinenlide S (NP0043762)

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Record Information

Version

1.0

Created at

2021-06-21 01:04:53 UTC

Updated at

2021-06-30 00:19:39 UTC

NP-MRD ID

NP0043762

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trichinenlide S

Provided By

JEOL Database JEOL Logo

Description

(1S,2S,5R,6R,9R,12S,13S,14S,16S)-12-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-9-{[(2E)-2-methylbut-2-enoyl]oxy}-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-14-yl (2E)-2-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. trichinenlide S is found in Trichilia sinensis. It was first documented in 2013 (Xu, J. -B., et al.). Based on a literature review very few articles have been published on (1S,2S,5R,6R,9R,12S,13S,14S,16S)-12-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-9-{[(2E)-2-methylbut-2-enoyl]oxy}-8,17-dioxo-7-oxatetracyclo[11.3.1.0²,¹¹.0⁵,¹⁰]Heptadec-10-en-14-yl (2E)-2-methylbut-2-enoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212103043D          

100104  0  0  0  0            999 V2000
    0.5603   -3.2263   -3.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898   -2.7880   -1.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -2.9086   -1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -3.4924   -1.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4464   -2.4668    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2179   -3.0588    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -1.3317    0.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -0.8024    1.8457 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4829   -0.8136    2.5592 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3182   -0.7457    4.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1526   -2.1880    2.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3391    0.3820    1.9764 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8262    0.3896    2.4231 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6955   -0.6184    1.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5788   -0.9107    0.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6406   -1.1135    2.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138   -2.0725    1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6232    1.7914    2.1626 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2706    2.6799    3.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    1.5782    2.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709    2.2049    3.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6192    0.5895    1.7694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9249    0.4563    2.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    1.2538    0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5505    2.4479    0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    2.3115    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5646    3.6277    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.2822   -0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3831    1.7564   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    1.5399   -1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8173    0.7957   -2.5326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0516    1.5117   -2.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955    0.7431   -3.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0712   -0.4758   -3.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077    1.5701   -3.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5729    0.7648   -3.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2109    2.9038   -3.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3144    3.8607   -3.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1814    0.6358   -3.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328    0.6281   -4.9781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    0.4995   -3.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750    0.7765   -2.8360 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4012    0.9433   -3.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670    0.3838   -2.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6381    0.7986   -3.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168    1.5663   -4.4724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652    1.6382   -4.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052    1.9820   -2.0137 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2216    3.2571   -2.8748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3647    2.3053   -0.8434 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7249    3.1775    0.2211 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4393    2.5739    0.8072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1940   -3.7732   -3.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8696   -2.3569   -3.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -3.8850   -2.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -2.3611   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2470   -2.9136   -1.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320   -3.4873   -2.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -4.5241   -1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5743   -1.4729    2.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -1.5785    4.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2844   -0.8300    4.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.1667    4.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685   -3.0081    2.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.3312    2.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4451   -2.3111    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662    0.1835    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995    1.3471    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    0.2408    3.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799   -1.6157    1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9455   -2.9373    1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2192   -2.4120    2.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    2.9626    3.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663    2.1745    4.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171    3.6189    3.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798    1.2647    2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2053    0.5409   -0.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093    4.3701   -0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084    3.9524    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6170    3.5167    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867   -0.2160   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4751    1.3804   -3.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881    0.1549   -4.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6478    0.0959   -2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2341    3.3812   -3.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2700    3.3767   -4.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4559    4.5545   -3.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0440    4.4451   -4.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -0.1319   -2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6176   -0.2463   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7055    0.6376   -3.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793    2.2071   -5.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6591    4.0284   -2.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    3.0723   -3.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875    3.6949   -3.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606    2.8193   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    1.3820   -0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4659    3.4003    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4816    4.1526   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    3.4513    1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  2  0  0  0  0
 48 50  1  0  0  0  0
 50 51  1  0  0  0  0
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 35 37  2  0  0  0  0
  5  3  1  0  0  0  0
 37 38  1  0  0  0  0
  5  6  2  0  0  0  0
 12 18  1  0  0  0  0
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  9  8  1  0  0  0  0
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  8 22  1  0  0  0  0
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  9 10  1  1  0  0  0
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  8  7  1  0  0  0  0
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 31 32  1  0  0  0  0
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M  END

     RDKit          3D

100104  0  0  0  0  0  0  0  0999 V2000
    0.5603   -3.2263   -3.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898   -2.7880   -1.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -2.9086   -1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -3.4924   -1.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4464   -2.4668    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2179   -3.0588    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -1.3317    0.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -0.8024    1.8457 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4829   -0.8136    2.5592 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3182   -0.7457    4.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1526   -2.1880    2.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306212103043D          

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M  END
> <DATABASE_ID>
NP0043762

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12C(=O)[C@](C([H])([H])[H])([C@]3([H])C(=C4[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C(=O)O[C@@]([H])(C5=C([H])OC([H])=C5[H])[C@]4(C([H])([H])[H])C([H])([H])C3([H])[H])[C@]1([H])OC(=O)C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C39H48O13/c1-11-19(3)31(42)50-28-27-26-23(13-15-37(27,8)29(51-33(28)44)22-14-16-48-18-22)38(9)24(17-25(41)47-10)36(6,7)35(52-32(43)20(4)12-2)39(46,34(38)45)30(26)49-21(5)40/h11-12,14,16,18,23-24,28-30,35,46H,13,15,17H2,1-10H3/b19-11+,20-12+/t23-,24-,28+,29-,30-,35-,37+,38+,39-/m0/s1

> <INCHI_KEY>
YEURVUNYHQSCIT-YIBUEILLSA-N

> <FORMULA>
C39H48O13

> <MOLECULAR_WEIGHT>
724.8

> <EXACT_MASS>
724.309491606

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
100

> <JCHEM_AVERAGE_POLARIZABILITY>
73.69736877199352

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,5R,6R,9R,12S,13S,14S,16S)-12-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-9-{[(2E)-2-methylbut-2-enoyl]oxy}-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-14-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.96

> <JCHEM_LOGP>
5.522656898666665

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.100258547898534

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888769758220418

> <JCHEM_POLAR_SURFACE_AREA>
181.94

> <JCHEM_REFRACTIVITY>
183.4201

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.10e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,6R,9R,12S,13S,14S,16S)-12-(acetyloxy)-6-(furan-3-yl)-13-hydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-9-{[(2E)-2-methylbut-2-enoyl]oxy}-8,17-dioxo-7-oxatetracyclo[11.3.1.0^{2,11}.0^{5,10}]heptadec-10-en-14-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

100104  0  0  0  0  0  0  0  0999 V2000
    0.5603   -3.2263   -3.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 57  1  0
  4 58  1  0
  4 59  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0       0.560  -3.226  -3.046  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.090  -2.788  -1.695  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.156  -2.909  -1.194  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.343  -3.492  -1.900  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.446  -2.467   0.200  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.218  -3.059   0.937  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.757  -1.332   0.503  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.927  -0.802   1.846  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.483  -0.814   2.559  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.318  -0.746   4.099  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.153  -2.188   2.295  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.339   0.382   1.976  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.826   0.390   2.423  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.696  -0.618   1.698  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.579  -0.911   0.515  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.641  -1.113   2.541  0.00  0.00           O+0
HETATM   17  C   UNK     0       5.514  -2.072   1.942  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.623   1.791   2.163  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.271   2.680   3.252  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.830   1.578   2.600  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.371   2.205   3.514  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.619   0.590   1.769  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.925   0.456   2.362  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.730   1.254   0.358  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.551   2.448   0.455  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.868   2.312   0.148  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.565   3.628   0.307  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.418   1.282  -0.212  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.383   1.756  -0.211  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.028   1.540  -1.492  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.817   0.796  -2.533  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.052   1.512  -2.689  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.095   0.743  -3.103  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.071  -0.476  -3.198  0.00  0.00           O+0
HETATM   35  C   UNK     0      -4.308   1.570  -3.398  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.573   0.765  -3.462  0.00  0.00           C+0
HETATM   37  C   UNK     0      -4.211   2.904  -3.578  0.00  0.00           C+0
HETATM   38  C   UNK     0      -5.314   3.861  -3.899  0.00  0.00           C+0
HETATM   39  C   UNK     0      -0.181   0.636  -3.936  0.00  0.00           C+0
HETATM   40  O   UNK     0      -0.833   0.628  -4.978  0.00  0.00           O+0
HETATM   41  O   UNK     0       1.163   0.500  -3.993  0.00  0.00           O+0
HETATM   42  C   UNK     0       1.975   0.777  -2.836  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.401   0.943  -3.285  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.567   0.384  -2.683  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.638   0.799  -3.437  0.00  0.00           C+0
HETATM   46  O   UNK     0       5.217   1.566  -4.472  0.00  0.00           O+0
HETATM   47  C   UNK     0       3.865   1.638  -4.386  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.405   1.982  -2.014  0.00  0.00           C+0
HETATM   49  C   UNK     0       1.222   3.257  -2.875  0.00  0.00           C+0
HETATM   50  C   UNK     0       2.365   2.305  -0.843  0.00  0.00           C+0
HETATM   51  C   UNK     0       1.725   3.178   0.221  0.00  0.00           C+0
HETATM   52  C   UNK     0       0.439   2.574   0.807  0.00  0.00           C+0
HETATM   53  H   UNK     0      -0.194  -3.773  -3.615  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.870  -2.357  -3.633  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.428  -3.885  -2.934  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.876  -2.361  -1.075  0.00  0.00           H+0
HETATM   57  H   UNK     0      -3.247  -2.914  -1.678  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.232  -3.487  -2.987  0.00  0.00           H+0
HETATM   59  H   UNK     0      -2.509  -4.524  -1.573  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.574  -1.473   2.426  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.301  -1.579   4.455  0.00  0.00           H+0
HETATM   62  H   UNK     0       1.284  -0.830   4.608  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.152   0.167   4.464  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.469  -3.008   2.544  0.00  0.00           H+0
HETATM   65  H   UNK     0       2.046  -2.331   2.913  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.445  -2.311   1.249  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.366   0.184   0.899  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.300   1.347   2.184  0.00  0.00           H+0
HETATM   69  H   UNK     0       2.906   0.241   3.504  0.00  0.00           H+0
HETATM   70  H   UNK     0       6.080  -1.616   1.124  0.00  0.00           H+0
HETATM   71  H   UNK     0       4.946  -2.937   1.585  0.00  0.00           H+0
HETATM   72  H   UNK     0       6.219  -2.412   2.705  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.303   2.963   3.038  0.00  0.00           H+0
HETATM   74  H   UNK     0       1.266   2.175   4.224  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.717   3.619   3.377  0.00  0.00           H+0
HETATM   76  H   UNK     0      -3.080   1.265   2.892  0.00  0.00           H+0
HETATM   77  H   UNK     0      -2.205   0.541  -0.320  0.00  0.00           H+0
HETATM   78  H   UNK     0      -4.109   4.370  -0.354  0.00  0.00           H+0
HETATM   79  H   UNK     0      -4.508   3.952   1.349  0.00  0.00           H+0
HETATM   80  H   UNK     0      -5.617   3.517   0.030  0.00  0.00           H+0
HETATM   81  H   UNK     0      -0.987  -0.216  -2.155  0.00  0.00           H+0
HETATM   82  H   UNK     0      -6.475   1.380  -3.454  0.00  0.00           H+0
HETATM   83  H   UNK     0      -5.588   0.155  -4.372  0.00  0.00           H+0
HETATM   84  H   UNK     0      -5.648   0.096  -2.598  0.00  0.00           H+0
HETATM   85  H   UNK     0      -3.234   3.381  -3.514  0.00  0.00           H+0
HETATM   86  H   UNK     0      -6.270   3.377  -4.108  0.00  0.00           H+0
HETATM   87  H   UNK     0      -5.456   4.555  -3.064  0.00  0.00           H+0
HETATM   88  H   UNK     0      -5.044   4.445  -4.784  0.00  0.00           H+0
HETATM   89  H   UNK     0       1.943  -0.132  -2.217  0.00  0.00           H+0
HETATM   90  H   UNK     0       4.618  -0.246  -1.805  0.00  0.00           H+0
HETATM   91  H   UNK     0       6.705   0.638  -3.378  0.00  0.00           H+0
HETATM   92  H   UNK     0       3.379   2.207  -5.168  0.00  0.00           H+0
HETATM   93  H   UNK     0       0.659   4.028  -2.336  0.00  0.00           H+0
HETATM   94  H   UNK     0       0.678   3.072  -3.806  0.00  0.00           H+0
HETATM   95  H   UNK     0       2.188   3.695  -3.148  0.00  0.00           H+0
HETATM   96  H   UNK     0       3.261   2.819  -1.215  0.00  0.00           H+0
HETATM   97  H   UNK     0       2.722   1.382  -0.381  0.00  0.00           H+0
HETATM   98  H   UNK     0       2.466   3.400   0.992  0.00  0.00           H+0
HETATM   99  H   UNK     0       1.482   4.153  -0.220  0.00  0.00           H+0
HETATM  100  H   UNK     0      -0.184   3.451   1.047  0.00  0.00           H+0
CONECT    1    2   53   54   55                                             
CONECT    2    3    1   56                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3   57   58   59                                             
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    9   22    7   60                                             
CONECT    9    8   10   11   12                                             
CONECT   10    9   61   62   63                                             
CONECT   11    9   64   65   66                                             
CONECT   12   18   67   13    9                                             
CONECT   13   12   14   68   69                                             
CONECT   14   15   13   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   70   71   72                                             
CONECT   18   12   20   52   19                                             
CONECT   19   18   73   74   75                                             
CONECT   20   22   18   21                                                  
CONECT   21   20                                                            
CONECT   22    8   20   24   23                                             
CONECT   23   22   76                                                       
CONECT   24   22   29   25   77                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   78   79   80                                             
CONECT   28   26                                                            
CONECT   29   30   24   52                                                  
CONECT   30   29   48   31                                                  
CONECT   31   30   39   32   81                                             
CONECT   32   31   33                                                       
CONECT   33   34   35   32                                                  
CONECT   34   33                                                            
CONECT   35   37   36   33                                                  
CONECT   36   35   82   83   84                                             
CONECT   37   35   38   85                                                  
CONECT   38   37   86   87   88                                             
CONECT   39   31   41   40                                                  
CONECT   40   39                                                            
CONECT   41   39   42                                                       
CONECT   42   48   41   43   89                                             
CONECT   43   42   47   44                                                  
CONECT   44   45   43   90                                                  
CONECT   45   46   44   91                                                  
CONECT   46   47   45                                                       
CONECT   47   43   46   92                                                  
CONECT   48   50   30   42   49                                             
CONECT   49   48   93   94   95                                             
CONECT   50   48   51   96   97                                             
CONECT   51   50   52   98   99                                             
CONECT   52   18   29  100   51                                             
CONECT   53    1                                                            
CONECT   54    1                                                            
CONECT   55    1                                                            
CONECT   56    2                                                            
CONECT   57    4                                                            
CONECT   58    4                                                            
CONECT   59    4                                                            
CONECT   60    8                                                            
CONECT   61   10                                                            
CONECT   62   10                                                            
CONECT   63   10                                                            
CONECT   64   11                                                            
CONECT   65   11                                                            
CONECT   66   11                                                            
CONECT   67   12                                                            
CONECT   68   13                                                            
CONECT   69   13                                                            
CONECT   70   17                                                            
CONECT   71   17                                                            
CONECT   72   17                                                            
CONECT   73   19                                                            
CONECT   74   19                                                            
CONECT   75   19                                                            
CONECT   76   23                                                            
CONECT   77   24                                                            
CONECT   78   27                                                            
CONECT   79   27                                                            
CONECT   80   27                                                            
CONECT   81   31                                                            
CONECT   82   36                                                            
CONECT   83   36                                                            
CONECT   84   36                                                            
CONECT   85   37                                                            
CONECT   86   38                                                            
CONECT   87   38                                                            
CONECT   88   38                                                            
CONECT   89   42                                                            
CONECT   90   44                                                            
CONECT   91   45                                                            
CONECT   92   47                                                            
CONECT   93   49                                                            
CONECT   94   49                                                            
CONECT   95   49                                                            
CONECT   96   50                                                            
CONECT   97   50                                                            
CONECT   98   51                                                            
CONECT   99   51                                                            
CONECT  100   52                                                            
MASTER        0    0    0    0    0    0    0    0  100    0  208    0
END

RDKit          3D

100104  0  0  0  0  0  0  0  0999 V2000
    0.5603   -3.2263   -3.0463 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0898   -2.7880   -1.6954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1562   -2.9086   -1.1935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3433   -3.4924   -1.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4464   -2.4668    0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2179   -3.0588    0.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7566   -1.3317    0.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9271   -0.8024    1.8457 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4829   -0.8136    2.5592 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3182   -0.7457    4.0994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1526   -2.1880    2.2952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3391    0.3820    1.9764 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8262    0.3896    2.4231 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6955   -0.6184    1.6976 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5788   -0.9107    0.5148 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6406   -1.1135    2.5408 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5138   -2.0725    1.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6232    1.7914    2.1626 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2706    2.6799    3.2518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8303    1.5782    2.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3709    2.2049    3.5144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6192    0.5895    1.7694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9249    0.4563    2.3618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7295    1.2538    0.3581 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5505    2.4479    0.4549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8683    2.3115    0.1475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5646    3.6277    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4184    1.2822   -0.2120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3831    1.7564   -0.2106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0281    1.5399   -1.4923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8173    0.7957   -2.5326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0516    1.5117   -2.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0955    0.7431   -3.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0712   -0.4758   -3.1977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3077    1.5701   -3.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5729    0.7648   -3.4622 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2109    2.9038   -3.5782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3144    3.8607   -3.8989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1814    0.6358   -3.9362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8328    0.6281   -4.9781 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1634    0.4995   -3.9927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9750    0.7765   -2.8360 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4012    0.9433   -3.2851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5670    0.3838   -2.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6381    0.7986   -3.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2168    1.5663   -4.4724 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8652    1.6382   -4.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4052    1.9820   -2.0137 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2216    3.2571   -2.8748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3647    2.3053   -0.8434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249    3.1775    0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4393    2.5739    0.8072 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1940   -3.7732   -3.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8696   -2.3569   -3.6330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -3.8850   -2.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8760   -2.3611   -1.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2470   -2.9136   -1.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2320   -3.4873   -2.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5094   -4.5241   -1.5735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5743   -1.4729    2.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3007   -1.5785    4.4552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2844   -0.8300    4.6081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.1667    4.4636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685   -3.0081    2.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0455   -2.3312    2.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4451   -2.3111    1.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3662    0.1835    0.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2995    1.3471    2.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9060    0.2408    3.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0799   -1.6157    1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9455   -2.9373    1.5851 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2192   -2.4120    2.7052 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3027    2.9626    3.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2663    2.1745    4.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171    3.6189    3.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0798    1.2647    2.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2053    0.5409   -0.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1093    4.3701   -0.3537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5084    3.9524    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6170    3.5167    0.0304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9867   -0.2160   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4751    1.3804   -3.4542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5881    0.1549   -4.3715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6478    0.0959   -2.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2341    3.3812   -3.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2700    3.3767   -4.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4559    4.5545   -3.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0440    4.4451   -4.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9427   -0.1319   -2.2166 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6176   -0.2463   -1.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7055    0.6376   -3.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3793    2.2071   -5.1675 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6591    4.0284   -2.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6782    3.0723   -3.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1875    3.6949   -3.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2606    2.8193   -1.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7223    1.3820   -0.3813 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4659    3.4003    0.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4816    4.1526   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1840    3.4513    1.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
 29 30  2  0
 48 50  1  0
 50 51  1  0
 48 30  1  0
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  9  8  1  0
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  8 22  1  0
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  9 10  1  1
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  9 11  1  0
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  4 58  1  0
  4 59  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1S,2S,5R,6R,9R,12S,13S,14S,16S)-12-(Acetyloxy)-6-(furan-3-yl)-13-hydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-9-{[(2E)-2-methylbut-2-enoyl]oxy}-8,17-dioxo-7-oxatetracyclo[11.3.1.0,.0,]heptadec-10-en-14-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₃₉H₄₈O₁₃

Average Mass

724.8000 Da

Monoisotopic Mass

724.30949 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@]12C(=O)[C@](C([H])([H])[H])([C@]3([H])C(=C4[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C(=O)O[C@@]([H])(C5=C([H])OC([H])=C5[H])[C@]4(C([H])([H])[H])C([H])([H])C3([H])[H])[C@]1([H])OC(=O)C([H])([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]2([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H]

InChI Identifier

InChI=1S/C39H48O13/c1-11-19(3)31(42)50-28-27-26-23(13-15-37(27,8)29(51-33(28)44)22-14-16-48-18-22)38(9)24(17-25(41)47-10)36(6,7)35(52-32(43)20(4)12-2)39(46,34(38)45)30(26)49-21(5)40/h11-12,14,16,18,23-24,28-30,35,46H,13,15,17H2,1-10H3/b19-11+,20-12+/t23-,24-,28+,29-,30-,35-,37+,38+,39-/m0/s1

InChI Key

YEURVUNYHQSCIT-YIBUEILLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Trichilia sinensis	JEOL database	Xu, J. -B., et al, J. Nat. Prod. 76, 1872 (2013)

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
Mexicanolide
Steroid lactone
12-hydroxysteroid
Hydroxysteroid
12-alpha-hydroxysteroid
Steroid
Pentacarboxylic acid or derivatives
Naphthopyran
Naphthalene
Delta valerolactone
Fatty acid ester
Delta_valerolactone
Fatty acyl
Oxane
Pyran
Cyclic alcohol
Furan
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary alcohol
Ketone
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Organooxygen compound
Organic oxygen 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	3.96	ALOGPS
logP	5.52	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	11.1	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	181.94 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	183.42 m³·mol⁻¹	ChemAxon
Polarizability	73.7 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	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

72703239

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu, J. -B., et al. (2013). Xu, J. -B., et al, J. Nat. Prod. 76, 1872 (2013). J. Nat. Prod..

Showing NP-Card for trichinenlide S (NP0043762)

MOL for NP0043762 (trichinenlide S)

3D MOL for NP0043762 (trichinenlide S)

3D SDF for NP0043762 (trichinenlide S)

3D-SDF for NP0043762 (trichinenlide S)

PDB for NP0043762 (trichinenlide S)

3D PDB for NP0043762 (trichinenlide S)

SMILES for NP0043762 (trichinenlide S)

INCHI for NP0043762 (trichinenlide S)

Structure for NP0043762 (trichinenlide S)

3D Structure for NP0043762 (trichinenlide S)