NP-MRD: Showing NP-Card for lonijaposide L (NP0036278)

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Record Information

Version

2.0

Created at

2021-06-20 19:29:37 UTC

Updated at

2021-06-30 00:07:51 UTC

NP-MRD ID

NP0036278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lonijaposide L

Provided By

JEOL Database JEOL Logo

Description

Lonijaposide L belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. lonijaposide L is found in Lonicera japonica. lonijaposide L was first documented in 2011 (Yu, Y., et al.). Based on a literature review very few articles have been published on Lonijaposide L.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202121293D          

 65 67  0  0  0  0            999 V2000
    3.0255    0.0431    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.3985    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2364   -1.6878    2.3978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -1.7592    3.5000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3938   -1.9098    4.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.9828    5.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3068   -2.0308    7.1037 C   0  0  2  0  0  0  0  0  0  0  0  0
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  2 39  1  0  0  0  0
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 18 53  1  0  0  0  0
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M  CHG  2  22  -1  30   1
M  END

     RDKit          3D

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M  CHG  2  22  -1  30   1
M  END


  Mrv1652306202121293D          

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   -2.3655    0.8294   -1.9684 O   0  5  0  0  0  1  0  0  0  0  0  0
   -0.1809   -0.3809   -0.0667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7179   -0.1861   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505   -0.8638   -2.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.3980    0.9898   -5.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3301    1.7298   -5.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    1.5208   -5.1677 N   0  3  0  0  0  4  0  0  0  0  0  0
   -1.0500    2.3887   -5.6102 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4645    3.3611   -4.5175 C   0  0  1  0  0  0  0  0  0  0  0  0
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    0.4157    4.7353   -4.9838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0084    4.2433   -2.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    0.5754   -4.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3373   -0.9961    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0174   -1.6006    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1571   -0.5369    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460   -0.8443    3.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8390   -1.0754    5.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099   -1.1136    7.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4315   -2.0634    9.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5447   -4.1381    5.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5642   -3.0073    7.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064   -2.3756    4.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1284   -4.5270    5.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4610   -3.8799    3.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1429   -1.6979   -2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -0.4545   -3.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1810   -5.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763    2.5136   -6.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    1.7242   -5.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    2.9092   -6.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1972    0.4562   -3.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0  0  0  0
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 23  3  1  0  0  0  0
 36 30  2  0  0  0  0
 29 28  2  0  0  0  0
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  3  4  1  0  0  0  0
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  4  5  1  0  0  0  0
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  6 15  1  0  0  0  0
 15 13  1  0  0  0  0
 13 11  1  0  0  0  0
 23 24  1  0  0  0  0
 19 20  1  0  0  0  0
 20 22  1  0  0  0  0
 11  8  1  0  0  0  0
  8  7  1  0  0  0  0
  2  1  2  3  0  0  0
  7  6  1  0  0  0  0
 20 21  2  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 30 31  1  0  0  0  0
 11 12  1  0  0  0  0
 31 32  1  0  0  0  0
 13 14  1  0  0  0  0
 32 33  1  0  0  0  0
 15 16  1  0  0  0  0
 33 35  1  0  0  0  0
 33 34  2  0  0  0  0
  3  2  1  0  0  0  0
  8  9  1  0  0  0  0
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  6 42  1  1  0  0  0
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  1 37  1  0  0  0  0
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 31 60  1  0  0  0  0
 31 61  1  0  0  0  0
 32 62  1  0  0  0  0
 32 63  1  0  0  0  0
 35 64  1  0  0  0  0
M  CHG  2  22  -1  30   1
M  END
> <DATABASE_ID>
NP0036278

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H29NO11/c1-2-14-15(6-5-13-4-3-8-25(10-13)9-7-18(27)28)16(22(32)33)12-34-23(14)36-24-21(31)20(30)19(29)17(11-26)35-24/h2-6,8,10,12,14-15,17,19-21,23-24,26,29-31H,1,7,9,11H2,(H-,27,28,32,33)/b6-5+/t14-,15+,17-,19-,20+,21-,23+,24+/m1/s1

> <INCHI_KEY>
ONSYQRQUUDJRLS-IRTUFKDUSA-N

> <FORMULA>
C24H29NO11

> <MOLECULAR_WEIGHT>
507.492

> <EXACT_MASS>
507.174060758

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
50.56513261663401

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(2-carboxyethyl)pyridin-1-ium

> <ALOGPS_LOGP>
-1.51

> <JCHEM_LOGP>
-4.7372143328050775

> <ALOGPS_LOGS>
-3.66

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.066240686382313

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.300347064210951

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615639986

> <JCHEM_POLAR_SURFACE_AREA>
189.92

> <JCHEM_REFRACTIVITY>
134.44369999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(2-carboxyethyl)pyridin-1-ium

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 65 67  0  0  0  0  0  0  0  0999 V2000
    3.0255    0.0431    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.3985    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -0.5845    1.2606 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.3068   -2.0308    7.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.9556   -3.1749    4.5164 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -1.1413    0.7736    0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    1.4886   -1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1809   -0.3809   -0.0667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7179   -0.1861   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505   -0.8638   -2.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8802   -0.1313   -3.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    0.0638   -4.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980    0.9898   -5.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3301    1.7298   -5.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    1.5208   -5.1677 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0500    2.3887   -5.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645    3.3611   -4.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    4.1892   -4.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157    4.7353   -4.9838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0084    4.2433   -2.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    0.5754   -4.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7923    0.7964    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373   -0.9961    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0174   -1.6006    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1571   -0.5369    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460   -0.8443    3.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8390   -1.0754    5.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7064   -2.3756    4.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1284   -4.5270    5.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4610   -3.8799    3.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323   -3.5802    2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    2.0798    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -1.2787   -0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1429   -1.6979   -2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -0.4545   -3.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1810   -5.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763    2.5136   -6.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    1.7242   -5.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    2.9092   -6.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476    4.0353   -4.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    2.8271   -3.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521    3.6702   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972    0.4562   -3.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  2  0
  9 10  1  0
 26 36  1  0
 23  3  1  0
 36 30  2  0
 29 28  2  0
 28 27  1  0
  3  4  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
  4  5  1  0
 23 19  1  0
 30 29  1  0
  6 15  1  0
 15 13  1  0
 13 11  1  0
 23 24  1  0
 19 20  1  0
 20 22  1  0
 11  8  1  0
  8  7  1  0
  2  1  2  3
  7  6  1  0
 20 21  2  0
 24 25  2  0
 25 26  1  0
 30 31  1  0
 11 12  1  0
 31 32  1  0
 13 14  1  0
 32 33  1  0
 15 16  1  0
 33 35  1  0
 33 34  2  0
  3  2  1  0
  8  9  1  0
  6  5  1  0
 36 65  1  0
 29 59  1  0
 28 58  1  0
 27 57  1  0
 25 56  1  0
  6 42  1  1
 11 47  1  6
 12 48  1  0
 13 49  1  1
 14 50  1  0
 15 51  1  6
 16 52  1  0
  9 44  1  0
  9 45  1  0
  8 43  1  1
 10 46  1  0
  2 39  1  0
  3 40  1  6
  4 41  1  1
 18 53  1  0
 23 54  1  6
 24 55  1  0
  1 37  1  0
  1 38  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 32 63  1  0
 35 64  1  0
M  CHG  2  22  -1  30   1
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       3.026   0.043   1.637  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.743   0.399   1.481  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.597  -0.585   1.261  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.414  -0.512   2.436  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.236  -1.688   2.398  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.141  -1.759   3.500  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.394  -1.910   4.714  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.225  -1.983   5.875  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.307  -2.031   7.104  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.063  -2.165   8.305  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.139  -3.216   5.808  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.063  -3.284   6.901  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.956  -3.175   4.516  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.706  -4.395   4.374  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.064  -2.981   3.291  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.911  -2.827   2.142  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.182   0.707   2.463  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.548   1.227   1.252  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.141   0.774   0.062  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.635   1.489  -1.178  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.162   2.650  -1.386  0.00  0.00           O+0
HETATM   22  O   UNK     0      -2.365   0.829  -1.968  0.00  0.00           O-1
HETATM   23  C   UNK     0      -0.181  -0.381  -0.067  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.718  -0.186  -1.273  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.551  -0.864  -2.422  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.880  -0.131  -3.642  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.176   0.064  -4.101  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.398   0.990  -5.116  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.330   1.730  -5.621  0.00  0.00           C+0
HETATM   30  N   UNK     0       0.073   1.521  -5.168  0.00  0.00           N+1
HETATM   31  C   UNK     0      -1.050   2.389  -5.610  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.464   3.361  -4.518  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.280   4.189  -4.133  0.00  0.00           C+0
HETATM   34  O   UNK     0       0.416   4.735  -4.984  0.00  0.00           O+0
HETATM   35  O   UNK     0       0.008   4.243  -2.827  0.00  0.00           O+0
HETATM   36  C   UNK     0      -0.168   0.575  -4.236  0.00  0.00           C+0
HETATM   37  H   UNK     0       3.792   0.796   1.790  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.337  -0.996   1.614  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.478   1.455   1.510  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.017  -1.601   1.235  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.157  -0.537   3.372  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.746  -0.844   3.536  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.839  -1.075   5.951  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.710  -1.114   7.160  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.608  -2.872   7.033  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.432  -2.063   9.041  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.545  -4.138   5.829  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.564  -3.007   7.703  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.706  -2.376   4.566  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.128  -4.527   5.248  0.00  0.00           H+0
HETATM   51  H   UNK     0      -2.461  -3.880   3.115  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.532  -3.580   2.179  0.00  0.00           H+0
HETATM   53  H   UNK     0      -2.205   2.080   1.377  0.00  0.00           H+0
HETATM   54  H   UNK     0      -0.794  -1.279  -0.234  0.00  0.00           H+0
HETATM   55  H   UNK     0       1.318   0.725  -1.253  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.143  -1.698  -2.495  0.00  0.00           H+0
HETATM   57  H   UNK     0       3.012  -0.455  -3.636  0.00  0.00           H+0
HETATM   58  H   UNK     0       3.408   1.181  -5.469  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.476   2.514  -6.359  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.879   1.724  -5.881  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.737   2.909  -6.522  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.248   4.035  -4.880  0.00  0.00           H+0
HETATM   63  H   UNK     0      -1.880   2.827  -3.668  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.552   3.670  -2.205  0.00  0.00           H+0
HETATM   65  H   UNK     0      -1.197   0.456  -3.913  0.00  0.00           H+0
CONECT    1    2   37   38                                                  
CONECT    2    1    3   39                                                  
CONECT    3   23    4    2   40                                             
CONECT    4    3   17    5   41                                             
CONECT    5    4    6                                                       
CONECT    6   15    7    5   42                                             
CONECT    7    8    6                                                       
CONECT    8   11    7    9   43                                             
CONECT    9   10    8   44   45                                             
CONECT   10    9   46                                                       
CONECT   11   13    8   12   47                                             
CONECT   12   11   48                                                       
CONECT   13   15   11   14   49                                             
CONECT   14   13   50                                                       
CONECT   15    6   13   16   51                                             
CONECT   16   15   52                                                       
CONECT   17    4   18                                                       
CONECT   18   17   19   53                                                  
CONECT   19   18   23   20                                                  
CONECT   20   19   22   21                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23    3   19   24   54                                             
CONECT   24   23   25   55                                                  
CONECT   25   24   26   56                                                  
CONECT   26   27   36   25                                                  
CONECT   27   26   28   57                                                  
CONECT   28   29   27   58                                                  
CONECT   29   28   30   59                                                  
CONECT   30   36   29   31                                                  
CONECT   31   30   32   60   61                                             
CONECT   32   31   33   62   63                                             
CONECT   33   32   35   34                                                  
CONECT   34   33                                                            
CONECT   35   33   64                                                       
CONECT   36   26   30   65                                                  
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    2                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    6                                                            
CONECT   43    8                                                            
CONECT   44    9                                                            
CONECT   45    9                                                            
CONECT   46   10                                                            
CONECT   47   11                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   16                                                            
CONECT   53   18                                                            
CONECT   54   23                                                            
CONECT   55   24                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   29                                                            
CONECT   60   31                                                            
CONECT   61   31                                                            
CONECT   62   32                                                            
CONECT   63   32                                                            
CONECT   64   35                                                            
CONECT   65   36                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  134    0
END

RDKit          3D

65 67  0  0  0  0  0  0  0  0999 V2000
    3.0255    0.0431    1.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431    0.3985    1.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5971   -0.5845    1.2606 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4140   -0.5123    2.4355 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2364   -1.6878    2.3978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -1.7592    3.5000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3938   -1.9098    4.7142 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2246   -1.9828    5.8745 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3068   -2.0308    7.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0634   -2.1651    8.3047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1393   -3.2164    5.8075 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.0631   -3.2844    6.9014 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9556   -3.1749    4.5164 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7058   -4.3947    4.3743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0641   -2.9805    3.2907 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9114   -2.8270    2.1418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1821    0.7066    2.4630 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5478    1.2272    1.2521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1413    0.7736    0.0621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6354    1.4886   -1.1779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1616    2.6500   -1.3862 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3655    0.8294   -1.9684 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.1809   -0.3809   -0.0667 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7179   -0.1861   -1.2728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5505   -0.8638   -2.4223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8802   -0.1313   -3.6421 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    0.0638   -4.1010 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3980    0.9898   -5.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3301    1.7298   -5.6214 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0726    1.5208   -5.1677 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.0500    2.3887   -5.6102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4645    3.3611   -4.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2803    4.1892   -4.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157    4.7353   -4.9838 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0084    4.2433   -2.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1676    0.5754   -4.2360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7923    0.7964    1.7895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373   -0.9961    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    1.4554    1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0174   -1.6006    1.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1571   -0.5369    3.3723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7460   -0.8443    3.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8390   -1.0754    5.9514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7099   -1.1136    7.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6079   -2.8718    7.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4315   -2.0634    9.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5447   -4.1381    5.8292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5642   -3.0073    7.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7064   -2.3756    4.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1284   -4.5270    5.2477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4610   -3.8799    3.1148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5323   -3.5802    2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    2.0798    1.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7944   -1.2787   -0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3181    0.7252   -1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1429   -1.6979   -2.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0118   -0.4545   -3.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1810   -5.4692 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4763    2.5136   -6.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8787    1.7242   -5.8814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7366    2.9092   -6.5224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2476    4.0353   -4.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8801    2.8271   -3.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5521    3.6702   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1972    0.4562   -3.9125 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  2  0
  9 10  1  0
 26 36  1  0
 23  3  1  0
 36 30  2  0
 29 28  2  0
 28 27  1  0
  3  4  1  0
  4 17  1  0
 17 18  1  0
 18 19  2  0
  4  5  1  0
 23 19  1  0
 30 29  1  0
  6 15  1  0
 15 13  1  0
 13 11  1  0
 23 24  1  0
 19 20  1  0
 20 22  1  0
 11  8  1  0
  8  7  1  0
  2  1  2  3
  7  6  1  0
 20 21  2  0
 24 25  2  0
 25 26  1  0
 30 31  1  0
 11 12  1  0
 31 32  1  0
 13 14  1  0
 32 33  1  0
 15 16  1  0
 33 35  1  0
 33 34  2  0
  3  2  1  0
  8  9  1  0
  6  5  1  0
 36 65  1  0
 29 59  1  0
 28 58  1  0
 27 57  1  0
 25 56  1  0
  6 42  1  1
 11 47  1  6
 12 48  1  0
 13 49  1  1
 14 50  1  0
 15 51  1  6
 16 52  1  0
  9 44  1  0
  9 45  1  0
  8 43  1  1
 10 46  1  0
  2 39  1  0
  3 40  1  6
  4 41  1  1
 18 53  1  0
 23 54  1  6
 24 55  1  0
  1 37  1  0
  1 38  1  0
 31 60  1  0
 31 61  1  0
 32 62  1  0
 32 63  1  0
 35 64  1  0
M  CHG  2  22  -1  30   1
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₉NO₁₁

Average Mass

507.4920 Da

Monoisotopic Mass

507.17406 Da

IUPAC Name

3-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(2-carboxyethyl)pyridin-1-ium

Traditional Name

3-[(E)-2-[(2S,3R,4S)-5-carboxy-3-ethenyl-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]ethenyl]-1-(2-carboxyethyl)pyridin-1-ium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H29NO11/c1-2-14-15(6-5-13-4-3-8-25(10-13)9-7-18(27)28)16(22(32)33)12-34-23(14)36-24-21(31)20(30)19(29)17(11-26)35-24/h2-6,8,10,12,14-15,17,19-21,23-24,26,29-31H,1,7,9,11H2,(H-,27,28,32,33)/b6-5+/t14-,15+,17-,19-,20+,21-,23+,24+/m1/s1

InChI Key

ONSYQRQUUDJRLS-IRTUFKDUSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, 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
Lonicera japonica	JEOL database	Yu, Y., et al, J. Nat. Prod. 74, 2151 (2011)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Glycosyl compound
Secoiridoid-skeleton
O-glycosyl compound
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Pyridinium
Pyridine
Heteroaromatic compound
Vinylogous ester
Carboxylic acid salt
Secondary alcohol
Acetal
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Azacycle
Organoheterocyclic compound
Polyol
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Organic salt
Organonitrogen compound
Organooxygen compound
Organic zwitterion
Organic oxygen compound
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

terpene glycoside (CHEBI:69650 )

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	-1.5	ALOGPS
logP	-4.7	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	3.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.92 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	134.44 m³·mol⁻¹	ChemAxon
Polarizability	50.57 Å³	ChemAxon
Number of Rings	3	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

28477841

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

56599872

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yu, Y., et al. (2011). Yu, Y., et al, J. Nat. Prod. 74, 2151 (2011). J. Nat. Prod..

Showing NP-Card for lonijaposide L (NP0036278)

MOL for NP0036278 (lonijaposide L)

3D MOL for NP0036278 (lonijaposide L)

3D SDF for NP0036278 (lonijaposide L)

3D-SDF for NP0036278 (lonijaposide L)

PDB for NP0036278 (lonijaposide L)

3D PDB for NP0036278 (lonijaposide L)

SMILES for NP0036278 (lonijaposide L)

INCHI for NP0036278 (lonijaposide L)

Structure for NP0036278 (lonijaposide L)

3D Structure for NP0036278 (lonijaposide L)