NP-MRD: Showing NP-Card for 2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile (NP0143281)

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Record Information

Version

2.0

Created at

2022-09-01 21:59:57 UTC

Updated at

2022-09-01 21:59:58 UTC

NP-MRD ID

NP0143281

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

Description

Simmondsin belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. 2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile is found in Simmondsia chinensis. 2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile was first documented in 2002 (PMID: 12456116). Based on a literature review a significant number of articles have been published on Simmondsin (PMID: 34641603) (PMID: 33812189) (PMID: 29558444) (PMID: 35797942) (PMID: 19501769) (PMID: 16462820).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022200002D          

 26 27  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  3  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
M  END

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
   -3.9190   -2.7949    1.8455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0783   -2.2549    0.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6343   -0.9782    1.2203 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1688   -0.9896    1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4697    0.3264    1.1383 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2316    0.2064   -0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211    0.3758    0.1051 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2591   -0.8078   -0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5902   -0.5281   -0.4911 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4612   -1.7610   -0.3713 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0371   -2.7544   -1.2504 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6136    0.0043   -1.9085 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9391    0.2559   -2.2461 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7634    1.2469   -1.9612 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8464    1.0974   -3.0015 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.5744   -0.6589 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9689    2.3672    0.0902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4230    1.4521    1.1092 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1173    2.5683    1.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1053    2.7685    2.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793    2.9222    3.0560 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7283    1.3949    0.4074 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6292    2.1815    1.1220 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2122   -0.0187    0.2248 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9835   -0.4080   -1.0892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1916   -0.6487   -1.7358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8096   -2.1669    1.9719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4022   -3.0575    2.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2918   -3.7677    1.4218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1094   -0.7346    2.2103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6466   -1.7845    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9430   -1.2672    2.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2840    0.5305    1.9217 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868    0.5681    1.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9696    0.2614    0.1871 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4895   -1.4739   -0.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5571   -2.0928    0.6683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1144   -3.6634   -0.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2433   -0.7893   -2.5896 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2893    0.9648   -1.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4314    2.0853   -2.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009    0.3878   -3.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2138    2.2057   -0.8793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9018    2.2213    1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8201    3.4130    1.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5888    1.8815   -0.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9679    1.7499    1.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3092   -0.0128    0.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0065   -0.9582   -2.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6846   -1.5371   -1.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8648    0.2389   -1.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
  5 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  3  0
 18 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 24  3  1  0
 16  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  1
  4 31  1  0
  4 32  1  0
  5 33  1  1
  7 34  1  1
  9 35  1  1
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  6
 13 40  1  0
 14 41  1  6
 15 42  1  0
 16 43  1  6
 17 44  1  0
 19 45  1  0
 22 46  1  6
 23 47  1  0
 24 48  1  1
 26 49  1  0
 26 50  1  0
 26 51  1  0
M  END


  Mrv1652309022200002D          

 26 27  0  0  1  0            999 V2000
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  6  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  7 16  1  0  0  0  0
 16 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  3  0  0  0  0
 18 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
  3 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0143281

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10+,11+,12+,13-,14+,15+,16+/m1/s1

> <INCHI_KEY>
KURSRHBVYUACKS-JICLZLQHSA-N

> <FORMULA>
C16H25NO9

> <MOLECULAR_WEIGHT>
375.374

> <EXACT_MASS>
375.152931389

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
36.6026676762024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(1Z,2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

> <ALOGPS_LOGP>
-1.30

> <JCHEM_LOGP>
-2.9112668076666663

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.012196483340826

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.182450926739444

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981083684476567

> <JCHEM_POLAR_SURFACE_AREA>
161.85999999999999

> <JCHEM_REFRACTIVITY>
85.85309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1Z,2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       1.334  -8.470   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   24                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    7   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19   22                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   18   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    3   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
2-(Cyanomethylene)-3-hydroxy-4,5-dimethoxycyclohexyl-beta-glucoside	MeSH

Chemical Formula

C₁₆H₂₅NO₉

Average Mass

375.3740 Da

Monoisotopic Mass

375.15293 Da

IUPAC Name

2-[(1Z,2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

Traditional Name

2-[(1Z,2S,3R,4S,6R)-2-hydroxy-3,4-dimethoxy-6-{[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@@H](O[C@H]2O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]2O)\C(=C/C#N)[C@H](O)[C@H]1OC

InChI Identifier

InChI=1S/C16H25NO9/c1-23-9-5-8(7(3-4-17)11(19)15(9)24-2)25-16-14(22)13(21)12(20)10(6-18)26-16/h3,8-16,18-22H,5-6H2,1-2H3/b7-3+/t8-,9+,10+,11+,12+,13-,14+,15+,16+/m1/s1

InChI Key

KURSRHBVYUACKS-JICLZLQHSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Simmondsia chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

Hexose monosaccharide
O-glycosyl compound
Cyclitol or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Secondary alcohol
Polyol
Acetal
Organoheterocyclic compound
Nitrile
Carbonitrile
Oxacycle
Ether
Dialkyl ether
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Alcohol
Primary alcohol
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	-1.3	ALOGPS
logP	-2.9	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	161.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	85.85 m³·mol⁻¹	ChemAxon
Polarizability	36.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00054415

Chemspider ID

31142816

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Simmondsin

METLIN ID

Not Available

PubChem Compound

76308614

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tietel Z, Melamed S, Eretz-Kdosha N, Guetta A, Gvirtz R, Ogen-Shtern N, Dag A, Cohen G: Anti-Herpes Simplex 1 Activity of Simmondsia chinensis (Jojoba) Wax. Molecules. 2021 Oct 7;26(19). pii: molecules26196059. doi: 10.3390/molecules26196059. [PubMed:34641603 ]
Feki F, Klisurova D, Masmoudi MA, Choura S, Denev P, Trendafilova A, Chamkha M, Sayadi S: Optimization of microwave assisted extraction of simmondsins and polyphenols from Jojoba (Simmondsia chinensis) seed cake using Box-Behnken statistical design. Food Chem. 2021 Sep 15;356:129670. doi: 10.1016/j.foodchem.2021.129670. Epub 2021 Mar 23. [PubMed:33812189 ]
Belhadj S, Hentati O, Hamdaoui G, Fakhreddine K, Maillard E, Dal S, Sigrist S: Beneficial Effect of Jojoba Seed Extracts on Hyperglycemia-Induced Oxidative Stress in RINm5f Beta Cells. Nutrients. 2018 Mar 20;10(3). pii: nu10030384. doi: 10.3390/nu10030384. [PubMed:29558444 ]
Lein S, Van Boven M, Holser R, Decuypere E, Flo G, Lievens S, Cokelaere M: Simultaneous determination of carbohydrates and simmondsins in jojoba seed meal (Simmondsia chinensis) by gas chromatography. J Chromatogr A. 2002 Nov 22;977(2):257-64. doi: 10.1016/s0021-9673(02)01410-3. [PubMed:12456116 ]
Feki F, Mahmoudi A, Denev P, Feki I, Ognyanov M, Georgiev Y, Choura S, Chamkha M, Trendafilova A, Sayadi S: A jojoba (Simmondsia chinensis) seed cake extracts express hepatoprotective activity against paracetamol-induced toxicity in rats. Biomed Pharmacother. 2022 Sep;153:113371. doi: 10.1016/j.biopha.2022.113371. Epub 2022 Jul 4. [PubMed:35797942 ]
Lievens S, Verbaeys I, Flo G, Briers R, Decuypere E, Cokelaere M: Disruption of the behavioral satiety sequence by simmondsin. Appetite. 2009 Jun;52(3):703-710. doi: 10.1016/j.appet.2009.03.010. Epub 2009 Mar 28. [PubMed:19501769 ]
Boozer CN, Herron AJ: Simmondsin for weight loss in rats. Int J Obes (Lond). 2006 Jul;30(7):1143-8. doi: 10.1038/sj.ijo.0803251. Epub 2006 Feb 7. [PubMed:16462820 ]
Lievens S, Flo G, Decuypere E, Van Boven M, Cokelaere M: Simmondsin: effects on meal patterns and choice behavior in rats. Physiol Behav. 2003 Apr;78(4-5):669-77. doi: 10.1016/s0031-9384(03)00039-8. [PubMed:12782222 ]
Baek JS, Kim HY, Abbott TP, Moon TW, Lee SB, Park CS, Park KH: Acarviosine-simmondsin, a novel compound obtained from acarviosine-glucose and simmondsin by Thermus maltogenic amylase and its in vivo effect on food intake and hyperglycemia. Biosci Biotechnol Biochem. 2003 Mar;67(3):532-9. doi: 10.1271/bbb.67.532. [PubMed:12723600 ]
Van Boven M, Laga M, Leonard S, Busson R, Holser R, Decuypere E, Flo G, Lievens S, Cokelaere M: Mechanism of simmondsin decomposition during sodium hydroxide treatment. J Agric Food Chem. 2003 Feb 26;51(5):1260-4. doi: 10.1021/jf025812o. [PubMed:12590465 ]
LOTUS database [Link]

Showing NP-Card for 2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile (NP0143281)

MOL for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

3D MOL for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

3D SDF for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

3D-SDF for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

PDB for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

3D PDB for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

SMILES for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

INCHI for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

Structure for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)

3D Structure for NP0143281 (2-[(1z,2s,3r,4s,6r)-2-hydroxy-3,4-dimethoxy-6-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclohexylidene]acetonitrile)