NP-MRD: Showing NP-Card for Pisumionoside (NP0025893)

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Record Information

Version

2.0

Created at

2021-06-19 17:53:58 UTC

Updated at

2021-06-29 23:51:06 UTC

NP-MRD ID

NP0025893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pisumionoside

Provided By

JEOL Database JEOL Logo

Description

Pisumionoside 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. Pisumionoside is found in Pisum sativum L. Pisumionoside was first documented in 2008 (PMID: 18816526). Based on a literature review a small amount of articles have been published on Pisumionoside (PMID: 34296582) (PMID: 29703100) (PMID: 26226753).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119543D          

 60 61  0  0  0  0            999 V2000
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   -3.9651    6.1147    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306192119543D          

 60 61  0  0  0  0            999 V2000
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   -0.4980    4.0583   -0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.7869    3.8821    0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111    3.8829    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    0.8481    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9152    0.1232    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559    1.7659    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5716    2.0486    3.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2748    2.4566    3.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850    0.7744    3.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450   -0.4591    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    0.7440    2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923    0.0445   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0888   -2.0759    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -4.3513    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -4.5395    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558   -4.6170    0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224   -6.6583    1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5739   -4.5256   -1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541   -6.4835   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522   -4.0545   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400   -5.1482   -3.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566   -2.0301   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2556   -2.0263   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    1.5800   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    1.9696    0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    3.5619   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    1.7941   -1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7587    2.7837   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1445    4.7782   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0  0  0  0
 19 16  1  0  0  0  0
 16 15  1  0  0  0  0
 15 14  1  0  0  0  0
 11  8  1  0  0  0  0
 12 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26  6  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
 19 20  1  0  0  0  0
 26 27  1  0  0  0  0
 21 22  1  0  0  0  0
  6  5  1  0  0  0  0
 12 13  1  0  0  0  0
 23 24  1  0  0  0  0
  8 10  1  0  0  0  0
  6  7  1  1  0  0  0
 26 28  1  6  0  0  0
 17 18  1  0  0  0  0
  5  4  2  0  0  0  0
 11 12  1  0  0  0  0
  4  2  1  0  0  0  0
 23 14  1  0  0  0  0
  2  1  1  0  0  0  0
 23 21  1  0  0  0  0
  2  3  2  0  0  0  0
 16 17  1  0  0  0  0
 14 13  1  0  0  0  0
 14 44  1  1  0  0  0
 19 49  1  6  0  0  0
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 22 52  1  0  0  0  0
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 25 55  1  0  0  0  0
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  9 35  1  0  0  0  0
  9 36  1  0  0  0  0
  9 37  1  0  0  0  0
 27 57  1  0  0  0  0
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  5 33  1  0  0  0  0
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  7 34  1  0  0  0  0
 28 60  1  0  0  0  0
  4 32  1  0  0  0  0
  1 29  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025893

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H32O9/c1-10(21)5-6-19(26)17(2,3)7-11(8-18(19,4)25)27-16-15(24)14(23)13(22)12(9-20)28-16/h5-6,11-16,20,22-26H,7-9H2,1-4H3/b6-5+/t11-,12+,13+,14-,15+,16+,18-,19+/m0/s1

> <INCHI_KEY>
PASRVRCWYGWSDQ-FBOCVPDYSA-N

> <FORMULA>
C19H32O9

> <MOLECULAR_WEIGHT>
404.456

> <EXACT_MASS>
404.20463261

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
42.39043546313506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-4-[(1R,2S,4S)-1,2-dihydroxy-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one

> <ALOGPS_LOGP>
-0.88

> <JCHEM_LOGP>
-1.5902255423333342

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.794571997140995

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.126853649030203

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083541572856

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
98.1031

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.29e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-[(1R,2S,4S)-1,2-dihydroxy-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 60 61  0  0  0  0  0  0  0  0999 V2000
   -3.9006    7.2293    2.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9651    6.1147    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8901    6.0267    1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396    5.1397    1.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931    4.0381    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8258    2.9583    1.0259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7050    3.4165    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931    1.5893    1.6619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6368    1.0625    1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4902    1.7313    3.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974    0.5115    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.3690   -0.0139 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3136   -0.5771   -0.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1130   -1.9356   -0.2360 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8518   -2.7404    0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5811   -4.1405    0.3843 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6523   -4.8623    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -6.2763    1.1560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776   -4.6305   -1.0731 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2010   -6.0083   -1.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -3.8110   -1.8802 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3545   -4.1686   -3.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791   -2.3116   -1.7326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2334   -1.6171   -2.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216    1.7000   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2519    2.8390   -0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2718    2.7257   -1.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    4.0583   -0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    6.9743    3.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8988    7.3957    3.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5430    8.1392    2.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972    5.3491    2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7869    3.8821    0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111    3.8829    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    0.8481    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9152    0.1232    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559    1.7659    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5716    2.0486    3.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2748    2.4566    3.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850    0.7744    3.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450   -0.4591    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    0.7440    2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923    0.0445   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0888   -2.0759    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -4.3513    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -4.5395    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558   -4.6170    0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224   -6.6583    1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5739   -4.5256   -1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541   -6.4835   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522   -4.0545   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400   -5.1482   -3.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566   -2.0301   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2556   -2.0263   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    1.5800   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    1.9696    0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    3.5619   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    1.7941   -1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7587    2.7837   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1445    4.7782   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0
 19 16  1  0
 16 15  1  0
 15 14  1  0
 11  8  1  0
 12 25  1  0
 25 26  1  0
 26  6  1  0
  6  8  1  0
  8  9  1  6
 19 20  1  0
 26 27  1  0
 21 22  1  0
  6  5  1  0
 12 13  1  0
 23 24  1  0
  8 10  1  0
  6  7  1  1
 26 28  1  6
 17 18  1  0
  5  4  2  0
 11 12  1  0
  4  2  1  0
 23 14  1  0
  2  1  1  0
 23 21  1  0
  2  3  2  0
 16 17  1  0
 14 13  1  0
 14 44  1  1
 19 49  1  6
 20 50  1  0
 21 51  1  1
 22 52  1  0
 23 53  1  6
 24 54  1  0
 17 46  1  0
 17 47  1  0
 16 45  1  1
 18 48  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  6
 25 55  1  0
 25 56  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
  5 33  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  7 34  1  0
 28 60  1  0
  4 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.901   7.229   2.914  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.965   6.115   1.904  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.890   6.027   1.100  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.840   5.140   1.899  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.893   4.038   1.130  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.826   2.958   1.026  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.705   3.417   1.827  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.293   1.589   1.662  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.637   1.063   1.109  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.490   1.731   3.197  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.197   0.511   1.446  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.755   0.369  -0.014  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.314  -0.577  -0.098  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.113  -1.936  -0.236  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.852  -2.740   0.451  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.581  -4.141   0.384  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.652  -4.862   1.214  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.478  -6.276   1.156  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.578  -4.630  -1.073  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.201  -6.008  -1.193  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.427  -3.811  -1.880  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.355  -4.169  -3.271  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.179  -2.312  -1.733  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.233  -1.617  -2.422  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.222   1.700  -0.535  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.252   2.839  -0.447  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.272   2.726  -1.587  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.498   4.058  -0.701  0.00  0.00           O+0
HETATM   29  H   UNK     0      -3.232   6.974   3.741  0.00  0.00           H+0
HETATM   30  H   UNK     0      -4.899   7.396   3.329  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.543   8.139   2.426  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.997   5.349   2.548  0.00  0.00           H+0
HETATM   33  H   UNK     0      -3.787   3.882   0.527  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.111   3.883   1.202  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.609   0.848   0.043  0.00  0.00           H+0
HETATM   36  H   UNK     0      -3.915   0.123   1.603  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.456   1.766   1.291  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.572   2.049   3.702  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.275   2.457   3.438  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.785   0.774   3.644  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.545  -0.459   1.823  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.314   0.744   2.058  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.592   0.045  -0.638  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.089  -2.076   0.246  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.395  -4.351   0.842  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.597  -4.540   2.259  0.00  0.00           H+0
HETATM   47  H   UNK     0       2.656  -4.617   0.848  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.122  -6.658   1.781  0.00  0.00           H+0
HETATM   49  H   UNK     0       1.574  -4.526  -1.520  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.654  -6.484  -0.460  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.452  -4.054  -1.572  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.340  -5.148  -3.275  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.757  -2.030  -2.231  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.256  -2.026  -3.312  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.128   1.580  -1.570  0.00  0.00           H+0
HETATM   56  H   UNK     0       0.692   1.970   0.014  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.978   3.562  -1.587  0.00  0.00           H+0
HETATM   58  H   UNK     0      -2.836   1.794  -1.579  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.759   2.784  -2.556  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.145   4.778  -0.825  0.00  0.00           H+0
CONECT    1    2   29   30   31                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2   32                                                  
CONECT    5    6    4   33                                                  
CONECT    6   26    8    5    7                                             
CONECT    7    6   34                                                       
CONECT    8   11    6    9   10                                             
CONECT    9    8   35   36   37                                             
CONECT   10    8   38   39   40                                             
CONECT   11    8   12   41   42                                             
CONECT   12   25   13   11   43                                             
CONECT   13   12   14                                                       
CONECT   14   15   23   13   44                                             
CONECT   15   16   14                                                       
CONECT   16   19   15   17   45                                             
CONECT   17   18   16   46   47                                             
CONECT   18   17   48                                                       
CONECT   19   21   16   20   49                                             
CONECT   20   19   50                                                       
CONECT   21   19   22   23   51                                             
CONECT   22   21   52                                                       
CONECT   23   24   14   21   53                                             
CONECT   24   23   54                                                       
CONECT   25   12   26   55   56                                             
CONECT   26   25    6   27   28                                             
CONECT   27   26   57   58   59                                             
CONECT   28   26   60                                                       
CONECT   29    1                                                            
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    4                                                            
CONECT   33    5                                                            
CONECT   34    7                                                            
CONECT   35    9                                                            
CONECT   36    9                                                            
CONECT   37    9                                                            
CONECT   38   10                                                            
CONECT   39   10                                                            
CONECT   40   10                                                            
CONECT   41   11                                                            
CONECT   42   11                                                            
CONECT   43   12                                                            
CONECT   44   14                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   17                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   20                                                            
CONECT   51   21                                                            
CONECT   52   22                                                            
CONECT   53   23                                                            
CONECT   54   24                                                            
CONECT   55   25                                                            
CONECT   56   25                                                            
CONECT   57   27                                                            
CONECT   58   27                                                            
CONECT   59   27                                                            
CONECT   60   28                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  122    0
END

RDKit          3D

60 61  0  0  0  0  0  0  0  0999 V2000
   -3.9006    7.2293    2.9137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9651    6.1147    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8901    6.0267    1.0996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8396    5.1397    1.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931    4.0381    1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8258    2.9583    1.0259 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7050    3.4165    1.8269 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2931    1.5893    1.6619 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6368    1.0625    1.1094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4902    1.7313    3.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1974    0.5115    1.4464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7554    0.3690   -0.0139 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3136   -0.5771   -0.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1130   -1.9356   -0.2360 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8518   -2.7404    0.4507 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5811   -4.1405    0.3843 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6523   -4.8623    1.2137 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4777   -6.2763    1.1560 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5776   -4.6305   -1.0731 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2010   -6.0083   -1.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4273   -3.8110   -1.8802 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3545   -4.1686   -3.2711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1791   -2.3116   -1.7326 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2334   -1.6171   -2.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2216    1.7000   -0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2519    2.8390   -0.4465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2718    2.7257   -1.5874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4980    4.0583   -0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2324    6.9743    3.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8988    7.3957    3.3285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5430    8.1392    2.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9972    5.3491    2.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7869    3.8821    0.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1111    3.8829    1.2018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    0.8481    0.0426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9152    0.1232    1.6034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4559    1.7659    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5716    2.0486    3.7020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2748    2.4566    3.4375 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7850    0.7744    3.6443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5450   -0.4591    1.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3137    0.7440    2.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5923    0.0445   -0.6380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0888   -2.0759    0.2460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3950   -4.3513    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5966   -4.5395    2.2593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6558   -4.6170    0.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1224   -6.6583    1.7812 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5739   -4.5256   -1.5200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541   -6.4835   -0.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4522   -4.0545   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3400   -5.1482   -3.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7566   -2.0301   -2.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2556   -2.0263   -3.3118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1281    1.5800   -1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6922    1.9696    0.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9781    3.5619   -1.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8355    1.7941   -1.5795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7587    2.7837   -2.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1445    4.7782   -0.8254 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 21  1  0
 19 16  1  0
 16 15  1  0
 15 14  1  0
 11  8  1  0
 12 25  1  0
 25 26  1  0
 26  6  1  0
  6  8  1  0
  8  9  1  6
 19 20  1  0
 26 27  1  0
 21 22  1  0
  6  5  1  0
 12 13  1  0
 23 24  1  0
  8 10  1  0
  6  7  1  1
 26 28  1  6
 17 18  1  0
  5  4  2  0
 11 12  1  0
  4  2  1  0
 23 14  1  0
  2  1  1  0
 23 21  1  0
  2  3  2  0
 16 17  1  0
 14 13  1  0
 14 44  1  1
 19 49  1  6
 20 50  1  0
 21 51  1  1
 22 52  1  0
 23 53  1  6
 24 54  1  0
 17 46  1  0
 17 47  1  0
 16 45  1  1
 18 48  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  6
 25 55  1  0
 25 56  1  0
  9 35  1  0
  9 36  1  0
  9 37  1  0
 27 57  1  0
 27 58  1  0
 27 59  1  0
  5 33  1  0
 10 38  1  0
 10 39  1  0
 10 40  1  0
  7 34  1  0
 28 60  1  0
  4 32  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₃₂O₉

Average Mass

404.4560 Da

Monoisotopic Mass

404.20463 Da

IUPAC Name

(3E)-4-[(1R,2S,4S)-1,2-dihydroxy-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one

Traditional Name

(3E)-4-[(1R,2S,4S)-1,2-dihydroxy-2,6,6-trimethyl-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexyl]but-3-en-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H32O9/c1-10(21)5-6-19(26)17(2,3)7-11(8-18(19,4)25)27-16-15(24)14(23)13(22)12(9-20)28-16/h5-6,11-16,20,22-26H,7-9H2,1-4H3/b6-5+/t11-,12+,13+,14-,15+,16+,18-,19+/m0/s1

InChI Key

PASRVRCWYGWSDQ-FBOCVPDYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₅D₅N, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₅D₅N, 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
Pisum sativum	JEOL database	Murakami, T., et al, Chem. Pharm. Bull. 49, 1003 (2001)

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
Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cyclohexanol
Cyclitol or derivatives
Oxane
Monosaccharide
Alpha,beta-unsaturated ketone
Tertiary alcohol
Acryloyl-group
Cyclic alcohol
Enone
Secondary alcohol
Ketone
Organoheterocyclic compound
Oxacycle
Polyol
Acetal
Alcohol
Carbonyl group
Primary alcohol
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-0.88	ALOGPS
logP	-1.6	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	12.13	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	98.1 m³·mol⁻¹	ChemAxon
Polarizability	42.39 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9037641

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10862351

PDB ID

Not Available

ChEBI ID

168297

Good Scents ID

Not Available

References

General References

Kuang H, Xia Y, Yang B, Wang Q, Lu S: Sesquiterpene Glucosides from Chloranthus japonicus Sieb. Chem Biodivers. 2008 Sep;5(9):1736-42. doi: 10.1002/cbdv.200890162. [PubMed:18816526 ]
Duan ZW, Wang SY, Pang X, Zhang J, Zhao Y, Zheng XH, Ma BP: [Terpenoids from leaves of Chinese hawthorn]. Zhongguo Zhong Yao Za Zhi. 2021 Jun;46(11):2830-2836. doi: 10.19540/j.cnki.cjcmm.20210222.601. [PubMed:34296582 ]
Shao JH, Chen J, Zhao CC, Shen J, Liu WY, Gu WY, Li KH: Insecticidal and alpha-glucosidase inhibitory activities of chemical constituents from Viburnum fordiae Hance. Nat Prod Res. 2019 Sep;33(18):2662-2667. doi: 10.1080/14786419.2018.1466130. Epub 2018 Apr 27. [PubMed:29703100 ]
Sheng W, Xu WD, Zhu CG, Yang YC, Shi JG: [Glycosides from Machilus wangchiana]. Zhongguo Zhong Yao Za Zhi. 2015 Mar;40(6):1102-7. [PubMed:26226753 ]
Murakami, T., et al. (2001). Murakami, T., et al, Chem. Pharm. Bull. 49, 1003 (2001). Chem. Pharm. Bull..

Showing NP-Card for Pisumionoside (NP0025893)

MOL for NP0025893 (Pisumionoside)

3D MOL for NP0025893 (Pisumionoside)

3D SDF for NP0025893 (Pisumionoside)

3D-SDF for NP0025893 (Pisumionoside)

PDB for NP0025893 (Pisumionoside)

3D PDB for NP0025893 (Pisumionoside)

SMILES for NP0025893 (Pisumionoside)

INCHI for NP0025893 (Pisumionoside)

Structure for NP0025893 (Pisumionoside)

3D Structure for NP0025893 (Pisumionoside)