NP-MRD: Showing NP-Card for trichinenlide N (NP0043757)

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Record Information

Version

1.0

Created at

2021-06-21 01:04:38 UTC

Updated at

2021-06-30 00:19:38 UTC

NP-MRD ID

NP0043757

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trichinenlide N

Provided By

JEOL Database JEOL Logo

Description

(1S,2S,5R,6R,9R,12S,13S,14S,16S)-12-(acetyloxy)-6-(furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-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 N 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)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-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          

 88 92  0  0  0  0            999 V2000
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   -1.7368   -2.1563    0.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 88 92  0  0  0  0  0  0  0  0999 V2000
   -2.4288    0.9162    2.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.2006    1.8193 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>
NP0043757

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])C(=O)O[C@@]([H])(C2=C([H])OC([H])=C2[H])[C@]2(C1=C1[C@]([H])(OC(=O)C([H])([H])[H])[C@]3(O[H])C(=O)[C@](C([H])([H])[H])([C@@]1([H])C([H])([H])C2([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]3([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C34H42O12/c1-9-16(2)27(38)46-30-31(4,5)20(14-21(36)42-8)33(7)19-10-12-32(6)23(22(19)26(44-17(3)35)34(30,41)29(33)40)24(37)28(39)45-25(32)18-11-13-43-15-18/h9,11,13,15,19-20,24-26,30,37,41H,10,12,14H2,1-8H3/b16-9+/t19-,20-,24+,25-,26-,30-,32+,33+,34-/m0/s1

> <INCHI_KEY>
DKCVSLKDJKIYEB-XJNAXTSQSA-N

> <FORMULA>
C34H42O12

> <MOLECULAR_WEIGHT>
642.698

> <EXACT_MASS>
642.267626792

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
88

> <JCHEM_AVERAGE_POLARIZABILITY>
64.5786359001967

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <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)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-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>
3.26

> <JCHEM_LOGP>
3.3097196639999997

> <ALOGPS_LOGS>
-4.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.129536940283277

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.057494939411445

> <JCHEM_PKA_STRONGEST_BASIC>
-2.888813638753546

> <JCHEM_POLAR_SURFACE_AREA>
175.87

> <JCHEM_REFRACTIVITY>
159.59029999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,6R,9R,12S,13S,14S,16S)-12-(acetyloxy)-6-(furan-3-yl)-9,13-dihydroxy-16-(2-methoxy-2-oxoethyl)-1,5,15,15-tetramethyl-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

 88 92  0  0  0  0  0  0  0  0999 V2000
   -2.4288    0.9162    2.8153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3984   -0.2006    1.8193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7305   -1.4912    2.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1815   -2.0920    3.3259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7124   -2.4675    0.8963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4702   -3.4212    0.8318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7368   -2.1563    0.0010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6307   -3.0010   -1.1781 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7613   -2.0684   -2.4473 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1507   -2.8954   -3.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9572   -1.1051   -2.2236 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3987   -1.2855   -2.6220 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4308   -0.1606   -3.6915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074    1.1143   -3.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0542    1.5507   -2.0820 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7404    1.7154   -4.2673 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3950    2.9388   -3.9267 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8477   -2.2626   -2.7721 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4166   -2.3303   -4.2088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4305   -3.6955   -2.4095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332   -4.6864   -3.0784 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205   -3.8403   -1.1019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6955   -5.2205   -0.9389 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7112   -3.4404   -0.0012 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7570   -4.4422    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7418   -5.2735    1.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065   -6.2129    1.0586 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9138   -5.2764    2.0320 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4353   -2.1071   -0.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6275   -1.1517    0.6728 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2217   -1.3481    2.1209 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0564   -2.3824    2.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2943   -0.1339    3.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2745   -0.2853    4.2874 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3776    1.0985    2.5259 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3995    1.2772    1.0945 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7872    2.7006    0.7993 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7986    3.4844    1.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7707    4.7199    0.8280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8054    4.7602   -0.1238 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052    3.5439   -0.1283 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889    0.2005    0.3887 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7334    0.1740    0.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3345    0.4813   -1.1332 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8098   -0.7112   -1.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9765   -1.9820   -1.7119 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4231    1.3233    2.9499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8101    0.6216    3.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0706    1.7201    2.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1093    0.1213    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2582   -2.2890    3.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6612   -3.0391    3.5083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9728   -1.4539    4.1877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4834   -3.6920   -1.2111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3135   -2.2500   -4.5688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0897   -3.4348   -3.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4154   -3.6429   -3.9938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2133   -0.5560   -3.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8555   -1.6624   -1.9316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7574   -0.3726   -1.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -0.7629   -1.6674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5824    0.1695   -3.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015   -0.5160   -4.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6677    3.6760   -3.5726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1678    2.7619   -3.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8741    3.3293   -4.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6489   -2.6554   -4.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2403   -3.0520   -4.2746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8153   -1.3814   -4.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0161   -5.7496   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1804   -3.4155    0.9525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8975   -6.8712    1.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8302   -6.8269    0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8406   -5.6455    1.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1822   -1.6827    2.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7843   -2.5107    3.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579    1.1578    0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4607    3.1827    2.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3360    5.6319    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3944    3.4297   -0.8358 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2912   -0.6929    0.5713 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7668    0.1222    2.0363 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2910    1.0684    0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3467    0.7809   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9990    1.3288   -1.3449 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8482   -0.4322   -3.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8520   -0.9255   -1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7045   -2.8030   -1.8216 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 22  1  0
 22 20  1  0
 20 18  1  0
 18 46  1  0
 42 36  1  0
 30 31  1  0
 31 33  1  0
 33 35  1  0
 35 36  1  0
  5  7  1  0
 36 37  1  0
 22 24  1  0
 42 43  1  1
 29 24  1  0
  9 10  1  6
 12  9  1  0
  9 11  1  0
 12 13  1  0
 12 61  1  1
  3  2  2  0
 33 34  2  0
 37 41  2  0
 13 14  1  0
 20 21  2  0
  8  7  1  0
 41 40  1  0
 40 39  1  0
 39 38  2  0
 38 37  1  0
 46 29  1  0
 14 15  2  0
  2  1  1  0
 14 16  1  0
  5  6  2  0
 16 17  1  0
  3  4  1  0
 18 19  1  6
  5  3  1  0
 22 23  1  1
 46 45  1  0
 46 88  1  1
 29 30  2  0
 31 32  1  0
 42 44  1  0
 24 25  1  0
 44 45  1  0
 25 26  1  0
 42 30  1  0
 26 27  1  0
 12 18  1  0
 26 28  2  0
  2 50  1  0
  1 47  1  0
  1 48  1  0
  1 49  1  0
  4 51  1  0
  4 52  1  0
  4 53  1  0
  8 54  1  1
 24 71  1  1
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 13 63  1  0
 44 84  1  0
 44 85  1  0
 45 86  1  0
 45 87  1  0
 31 75  1  6
 36 77  1  6
 43 81  1  0
 43 82  1  0
 43 83  1  0
 10 55  1  0
 10 56  1  0
 10 57  1  0
 11 58  1  0
 11 59  1  0
 11 60  1  0
 41 80  1  0
 39 79  1  0
 38 78  1  0
 17 64  1  0
 17 65  1  0
 17 66  1  0
 19 67  1  0
 19 68  1  0
 19 69  1  0
 23 70  1  0
 32 76  1  0
 27 72  1  0
 27 73  1  0
 27 74  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      -2.429   0.916   2.815  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.398  -0.201   1.819  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.731  -1.491   2.027  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.182  -2.092   3.326  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.712  -2.467   0.896  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.470  -3.421   0.832  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.737  -2.156   0.001  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.631  -3.001  -1.178  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.761  -2.068  -2.447  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.151  -2.895  -3.699  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.957  -1.105  -2.224  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.399  -1.286  -2.622  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.431  -0.161  -3.692  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.107   1.114  -3.224  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.054   1.551  -2.082  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.740   1.715  -4.267  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.395   2.939  -3.927  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.848  -2.263  -2.772  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.417  -2.330  -4.209  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.431  -3.696  -2.410  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.733  -4.686  -3.078  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.321  -3.840  -1.102  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.696  -5.221  -0.939  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.711  -3.440  -0.001  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.757  -4.442   0.054  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.742  -5.274   1.133  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.906  -6.213   1.059  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.914  -5.276   2.032  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.435  -2.107  -0.278  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.628  -1.152   0.673  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.222  -1.348   2.121  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.056  -2.382   2.640  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.294  -0.134   3.066  0.00  0.00           C+0
HETATM   34  O   UNK     0       1.274  -0.285   4.287  0.00  0.00           O+0
HETATM   35  O   UNK     0       1.378   1.099   2.526  0.00  0.00           O+0
HETATM   36  C   UNK     0       1.399   1.277   1.095  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.787   2.701   0.799  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.799   3.484   1.429  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.771   4.720   0.828  0.00  0.00           C+0
HETATM   40  O   UNK     0       1.805   4.760  -0.124  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.205   3.544  -0.128  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.289   0.201   0.389  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.733   0.174   0.944  0.00  0.00           C+0
HETATM   44  C   UNK     0       2.334   0.481  -1.133  0.00  0.00           C+0
HETATM   45  C   UNK     0       2.810  -0.711  -1.946  0.00  0.00           C+0
HETATM   46  C   UNK     0       1.976  -1.982  -1.712  0.00  0.00           C+0
HETATM   47  H   UNK     0      -1.423   1.323   2.950  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.810   0.622   3.795  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.071   1.720   2.441  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.109   0.121   0.819  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.258  -2.289   3.301  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.661  -3.039   3.508  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.973  -1.454   4.188  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.483  -3.692  -1.211  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.313  -2.250  -4.569  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.090  -3.435  -3.525  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.415  -3.643  -3.994  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.213  -0.556  -3.136  0.00  0.00           H+0
HETATM   59  H   UNK     0      -3.856  -1.662  -1.932  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.757  -0.373  -1.437  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.273  -0.763  -1.667  0.00  0.00           H+0
HETATM   62  H   UNK     0       0.582   0.170  -3.941  0.00  0.00           H+0
HETATM   63  H   UNK     0      -0.902  -0.516  -4.613  0.00  0.00           H+0
HETATM   64  H   UNK     0      -1.668   3.676  -3.573  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.168   2.762  -3.172  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.874   3.329  -4.829  0.00  0.00           H+0
HETATM   67  H   UNK     0       0.649  -2.655  -4.920  0.00  0.00           H+0
HETATM   68  H   UNK     0       2.240  -3.052  -4.275  0.00  0.00           H+0
HETATM   69  H   UNK     0       1.815  -1.381  -4.572  0.00  0.00           H+0
HETATM   70  H   UNK     0      -0.016  -5.750  -1.405  0.00  0.00           H+0
HETATM   71  H   UNK     0       0.180  -3.416   0.953  0.00  0.00           H+0
HETATM   72  H   UNK     0       2.898  -6.871   1.932  0.00  0.00           H+0
HETATM   73  H   UNK     0       2.830  -6.827   0.158  0.00  0.00           H+0
HETATM   74  H   UNK     0       3.841  -5.646   1.061  0.00  0.00           H+0
HETATM   75  H   UNK     0       0.182  -1.683   2.170  0.00  0.00           H+0
HETATM   76  H   UNK     0       1.784  -2.511   3.570  0.00  0.00           H+0
HETATM   77  H   UNK     0       0.358   1.158   0.761  0.00  0.00           H+0
HETATM   78  H   UNK     0       3.461   3.183   2.230  0.00  0.00           H+0
HETATM   79  H   UNK     0       3.336   5.632   0.961  0.00  0.00           H+0
HETATM   80  H   UNK     0       0.394   3.430  -0.836  0.00  0.00           H+0
HETATM   81  H   UNK     0       4.291  -0.693   0.571  0.00  0.00           H+0
HETATM   82  H   UNK     0       3.767   0.122   2.036  0.00  0.00           H+0
HETATM   83  H   UNK     0       4.291   1.068   0.646  0.00  0.00           H+0
HETATM   84  H   UNK     0       1.347   0.781  -1.492  0.00  0.00           H+0
HETATM   85  H   UNK     0       2.999   1.329  -1.345  0.00  0.00           H+0
HETATM   86  H   UNK     0       2.848  -0.432  -3.001  0.00  0.00           H+0
HETATM   87  H   UNK     0       3.852  -0.926  -1.675  0.00  0.00           H+0
HETATM   88  H   UNK     0       2.704  -2.803  -1.822  0.00  0.00           H+0
CONECT    1    2   47   48   49                                             
CONECT    2    3    1   50                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3   51   52   53                                             
CONECT    5    7    6    3                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    9   22    7   54                                             
CONECT    9    8   10   12   11                                             
CONECT   10    9   55   56   57                                             
CONECT   11    9   58   59   60                                             
CONECT   12    9   13   61   18                                             
CONECT   13   12   14   62   63                                             
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   64   65   66                                             
CONECT   18   20   46   19   12                                             
CONECT   19   18   67   68   69                                             
CONECT   20   22   18   21                                                  
CONECT   21   20                                                            
CONECT   22    8   20   24   23                                             
CONECT   23   22   70                                                       
CONECT   24   22   29   25   71                                             
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26   72   73   74                                             
CONECT   28   26                                                            
CONECT   29   24   46   30                                                  
CONECT   30   31   29   42                                                  
CONECT   31   30   33   32   75                                             
CONECT   32   31   76                                                       
CONECT   33   31   35   34                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   42   35   37   77                                             
CONECT   37   36   41   38                                                  
CONECT   38   39   37   78                                                  
CONECT   39   40   38   79                                                  
CONECT   40   41   39                                                       
CONECT   41   37   40   80                                                  
CONECT   42   36   43   44   30                                             
CONECT   43   42   81   82   83                                             
CONECT   44   42   45   84   85                                             
CONECT   45   46   44   86   87                                             
CONECT   46   18   29   45   88                                             
CONECT   47    1                                                            
CONECT   48    1                                                            
CONECT   49    1                                                            
CONECT   50    2                                                            
CONECT   51    4                                                            
CONECT   52    4                                                            
CONECT   53    4                                                            
CONECT   54    8                                                            
CONECT   55   10                                                            
CONECT   56   10                                                            
CONECT   57   10                                                            
CONECT   58   11                                                            
CONECT   59   11                                                            
CONECT   60   11                                                            
CONECT   61   12                                                            
CONECT   62   13                                                            
CONECT   63   13                                                            
CONECT   64   17                                                            
CONECT   65   17                                                            
CONECT   66   17                                                            
CONECT   67   19                                                            
CONECT   68   19                                                            
CONECT   69   19                                                            
CONECT   70   23                                                            
CONECT   71   24                                                            
CONECT   72   27                                                            
CONECT   73   27                                                            
CONECT   74   27                                                            
CONECT   75   31                                                            
CONECT   76   32                                                            
CONECT   77   36                                                            
CONECT   78   38                                                            
CONECT   79   39                                                            
CONECT   80   41                                                            
CONECT   81   43                                                            
CONECT   82   43                                                            
CONECT   83   43                                                            
CONECT   84   44                                                            
CONECT   85   44                                                            
CONECT   86   45                                                            
CONECT   87   45                                                            
CONECT   88   46                                                            
MASTER        0    0    0    0    0    0    0    0   88    0  184    0
END

RDKit          3D

88 92  0  0  0  0  0  0  0  0999 V2000
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M  END

View in JSmol

Synonyms

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

Chemical Formula

C₃₄H₄₂O₁₂

Average Mass

642.6980 Da

Monoisotopic Mass

642.26763 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C(=O)O[C@@]([H])(C2=C([H])OC([H])=C2[H])[C@]2(C1=C1[C@]([H])(OC(=O)C([H])([H])[H])[C@]3(O[H])C(=O)[C@](C([H])([H])[H])([C@@]1([H])C([H])([H])C2([H])[H])[C@@]([H])(C([H])([H])C(=O)OC([H])([H])[H])C(C([H])([H])[H])(C([H])([H])[H])[C@]3([H])OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C34H42O12/c1-9-16(2)27(38)46-30-31(4,5)20(14-21(36)42-8)33(7)19-10-12-32(6)23(22(19)26(44-17(3)35)34(30,41)29(33)40)24(37)28(39)45-25(32)18-11-13-43-15-18/h9,11,13,15,19-20,24-26,30,37,41H,10,12,14H2,1-8H3/b16-9+/t19-,20-,24+,25-,26-,30-,32+,33+,34-/m0/s1

InChI Key

DKCVSLKDJKIYEB-XJNAXTSQSA-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
Naphthopyran
Tetracarboxylic acid or derivatives
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
Lactone
Ketone
Carboxylic acid ester
Secondary alcohol
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	3.26	ALOGPS
logP	3.31	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	11.06	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	175.87 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	159.59 m³·mol⁻¹	ChemAxon
Polarizability	64.58 Å³	ChemAxon
Number of Rings	5	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

72700786

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 N (NP0043757)

MOL for NP0043757 (trichinenlide N)

3D MOL for NP0043757 (trichinenlide N)

3D SDF for NP0043757 (trichinenlide N)

3D-SDF for NP0043757 (trichinenlide N)

PDB for NP0043757 (trichinenlide N)

3D PDB for NP0043757 (trichinenlide N)

SMILES for NP0043757 (trichinenlide N)

INCHI for NP0043757 (trichinenlide N)

Structure for NP0043757 (trichinenlide N)

3D Structure for NP0043757 (trichinenlide N)