NP-MRD: Showing NP-Card for Secoxyloganin (NP0071835)

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Record Information

Version

2.0

Created at

2022-04-28 17:11:03 UTC

Updated at

2022-04-28 17:11:03 UTC

NP-MRD ID

NP0071835

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Secoxyloganin

Description

Secoxyloganin 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. Thus, secoxyloganin is considered to be an isoprenoid. Secoxyloganin is found in Acicarpha tribuloides, Adina racemosa, Calycophyllum spruceanum , Citronella gongonha, Gentiana rhodantha, Guettarda platypoda, Hydrangea macrophylla, Klaprothia mentzelioides, Lippia graveolens , Lippia origanoides, Loasa acerifolia, Lonicera japonica , Lonicera periclymenum, Morinda coreia, Phillyrea latifolia, Picconia excelsa, Rauwolfia serpentina, Sinoadina racemosa, Strychnos lucida and Strychnos spinosa . Secoxyloganin was first documented in 2021 (PMID: 34574160). Based on a literature review a small amount of articles have been published on secoxyloganin (PMID: 35137662) (PMID: 34147039) (PMID: 33124697).

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652304282219112D          

 28 29  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  1  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
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -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
    0.7145   -1.2375    0.0000 C   0  0  0  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
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  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
    3.5724   -1.2375    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  4  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 11 24  1  6  0  0  0
 24 25  2  0  0  0  0
  3 26  1  1  0  0  0
  2 27  1  6  0  0  0
  1 28  1  1  0  0  0
M  END

     RDKit          3D

 52 53  0  0  0  0  0  0  0  0999 V2000
   -1.5286   -0.3108   -2.8409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6092   -1.0902   -1.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0475   -0.7737   -0.4957 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2743    0.4843   -0.3498 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8049    0.3382    0.5386 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0355    0.5812   -0.0847 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7204   -0.6372   -0.0840 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0581   -0.4781   -0.4262 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6530   -1.8665   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9992   -1.7633   -0.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8267    0.2665    0.6481 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7325    1.1720    0.0986 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8255    1.0087    1.5045 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1219    0.0682    2.2322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8294    1.6702    0.5563 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5076    2.4131   -0.4225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0588    1.5493    0.2115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4192    1.5462   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0564    0.3714    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4860    0.3406   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2135   -0.6802   -0.0621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1807    1.5045   -0.5346 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5722    1.4964   -0.7924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953   -0.7289    0.5051 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8031   -2.0280    0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7286   -1.8815    1.9721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650   -2.8191    2.3531 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7906   -0.6809    2.6462 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0338    0.6405   -2.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9726   -0.5945   -3.8182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -2.0653   -1.8657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4354   -1.6765   -0.1847 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1872    0.7576   -1.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8949    0.8414   -1.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1609    0.0317   -1.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5612   -2.3801    0.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1332   -2.4347   -1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2523   -0.8355   -1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3263   -0.4633    1.3166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6654    2.0128    0.5913 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2904    1.7559    2.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5689   -0.8005    2.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2654    2.3851    1.1543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8262    3.0471   -0.8012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9769    2.4325   -0.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9912    0.4869   -0.9021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7824    2.0209   -1.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1273    2.0780   -0.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6782   -0.3922    1.4614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2611   -2.5656   -0.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9465   -2.7060    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4838   -0.6483    3.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 20  1  0
 20 21  2  0
 20 19  1  0
 19 18  2  0
 18 17  1  0
 17  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
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  3 24  1  0
 24 25  1  0
 25 26  1  0
 26 28  1  0
 26 27  2  0
 24 19  1  0
 15  6  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 18 45  1  0
  4 33  1  6
  6 34  1  6
  8 35  1  6
  9 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  1
 12 40  1  0
 13 41  1  1
 14 42  1  0
 15 43  1  1
 16 44  1  0
  3 32  1  1
  2 31  1  0
  1 29  1  0
  1 30  1  0
 24 49  1  1
 25 50  1  0
 25 51  1  0
 28 52  1  0
M  END

  Mrv1652304282219112D          

 28 29  0  0  1  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  1  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
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -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
    0.7145   -1.2375    0.0000 C   0  0  0  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
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  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
    3.5724   -1.2375    0.0000 O   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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  8  1  0  0  0  0
  4  9  1  6  0  0  0
 10  9  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 10 15  1  0  0  0  0
 13 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 12 20  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 11 24  1  6  0  0  0
 24 25  2  0  0  0  0
  3 26  1  1  0  0  0
  2 27  1  6  0  0  0
  1 28  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0071835

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1

> <INCHI_KEY>
MQLSOVRLZHTATK-PEYNGXJCSA-N

> <FORMULA>
C17H24O11

> <MOLECULAR_WEIGHT>
404.368

> <EXACT_MASS>
404.131861593

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.7817254701385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid

> <ALOGPS_LOGP>
-1.37

> <JCHEM_LOGP>
-1.5313349473333333

> <ALOGPS_LOGS>
-1.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.207016198119142

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8697267975186844

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592584

> <JCHEM_POLAR_SURFACE_AREA>
172.21

> <JCHEM_REFRACTIVITY>
89.446

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667 -13.860   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   28                                                  
CONECT    2    1    3   27                                                  
CONECT    3    2    4   26                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12   24                                                  
CONECT   12   11   13   20                                                  
CONECT   13   12   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16   13   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   11   25                                                       
CONECT   25   24                                                            
CONECT   26    3                                                            
CONECT   27    2                                                            
CONECT   28    1                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

View in JSmol

Synonyms

Value	Source
Secoxy-loganin	MeSH

Chemical Formula

C₁₇H₂₄O₁₁

Average Mass

404.3680 Da

Monoisotopic Mass

404.13186 Da

IUPAC Name

2-[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid

Traditional Name

[(2S,3R,4S)-3-ethenyl-5-(methoxycarbonyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-4-yl]acetic acid

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H](C=C)[C@@H]1CC(O)=O

InChI Identifier

InChI=1S/C17H24O11/c1-3-7-8(4-11(19)20)9(15(24)25-2)6-26-16(7)28-17-14(23)13(22)12(21)10(5-18)27-17/h3,6-8,10,12-14,16-18,21-23H,1,4-5H2,2H3,(H,19,20)/t7-,8+,10-,12-,13+,14-,16+,17+/m1/s1

InChI Key

MQLSOVRLZHTATK-PEYNGXJCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acicarpha tribuloides	LOTUS Database	35616633
Adina racemosa	Plant	KNApSAcK
Calycophyllum spruceanum	Plant	KNApSAcK
Citronella gongonha	LOTUS Database	35616633
Gentiana rhodantha	Plant	KNApSAcK
Guettarda platypoda	LOTUS Database	35616633
Hydrangea macrophylla	LOTUS Database	35616633
Klaprothia mentzelioides	LOTUS Database	35616633
Lippia graveolens	Plant	KNApSAcK
Lippia origanoides	LOTUS Database	35616633
Loasa acerifolia	Plant	KNApSAcK
Lonicera japonica	Plant	KNApSAcK
Lonicera periclymenum	LOTUS Database	35616633
Morinda coreia	Plant	KNApSAcK
Phillyrea latifolia	LOTUS Database	35616633
Picconia excelsa	LOTUS Database	35616633
Rauvolfia serpentina	Plant	KNApSAcK
Sinoadina racemosa	Plant	KNApSAcK
Strychnos lucida	Plant	KNApSAcK
Strychnos spinosa	Plant	KNApSAcK

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
Monocyclic monoterpenoid
Monoterpenoid
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Carboxylic acid ester
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
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	-1.4	ALOGPS
logP	-1.5	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	89.45 m³·mol⁻¹	ChemAxon
Polarizability	38.78 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

C00031346

Chemspider ID

142980

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162868

PDB ID

Not Available

ChEBI ID

132712

Good Scents ID

Not Available

References

General References

Nakayama H, Nishi N, Matsuo Y, Tanaka T, Kotoda N, Ishimaru K: A new secoiridoid glucoside from Olea europaea. J Asian Nat Prod Res. 2022 Feb 9:1-8. doi: 10.1080/10286020.2021.2017898. [PubMed:35137662 ]
Abbattista R, Losito I, Calvano CD, Cataldi TRI: Exploring the Isomeric Precursors of Olive Oil Major Secoiridoids: An Insight into Olive Leaves and Drupes by Liquid-Chromatography and Fourier-Transform Tandem Mass Spectrometry. Foods. 2021 Aug 31;10(9). pii: foods10092050. doi: 10.3390/foods10092050. [PubMed:34574160 ]
Xu QD, Zhou ZQ, Yu J, He Q, Sun Q, Zeng WC: Effect of Cedrus deodara extract on the physiochemical and sensory properties of salted meat and its action mechanism. J Food Sci. 2021 Jul;86(7):2910-2923. doi: 10.1111/1750-3841.15801. Epub 2021 Jun 19. [PubMed:34147039 ]
Rodriguez-Lopez CE, Hong B, Paetz C, Nakamura Y, Koudounas K, Passeri V, Baldoni L, Alagna F, Calderini O, O'Connor SE: Two bi-functional cytochrome P450 CYP72 enzymes from olive (Olea europaea) catalyze the oxidative C-C bond cleavage in the biosynthesis of secoxy-iridoids - flavor and quality determinants in olive oil. New Phytol. 2021 Feb;229(4):2288-2301. doi: 10.1111/nph.16975. Epub 2020 Oct 30. [PubMed:33124697 ]

Showing NP-Card for Secoxyloganin (NP0071835)

MOL for NP0071835 (Secoxyloganin)

3D MOL for NP0071835 (Secoxyloganin)

3D SDF for NP0071835 (Secoxyloganin)

3D-SDF for NP0071835 (Secoxyloganin)

PDB for NP0071835 (Secoxyloganin)

3D PDB for NP0071835 (Secoxyloganin)

SMILES for NP0071835 (Secoxyloganin)

INCHI for NP0071835 (Secoxyloganin)

Structure for NP0071835 (Secoxyloganin)

3D Structure for NP0071835 (Secoxyloganin)