NP-MRD: Showing NP-Card for Secologanin (NP0051780)

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Record Information

Version

2.0

Created at

2022-04-27 23:01:02 UTC

Updated at

2022-04-27 23:01:02 UTC

NP-MRD ID

NP0051780

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Secologanin

Description

Methyl (2R,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate 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. Secologanin is found in Adina racemosa, Alangium lamarckii, Alangium salviifolium , Carapichea affinis, Catharanthus roseus , Centaurium erythraea , Cephaelis acuminata, Cornus officinalis , Laurencia dendroidea, Lippia graveolens , Lippia origanoides, Lonicera caerulea, Lonicera japonica Thunb. , Lonicera morrowii, Lonicera periclymenum, Lonicera spp., Mentzelia albescens, Ophiorrhiza pumila, Psychotria burucana, Psychotria ipecacuanha , Psychotria klugii, Rehmannia glutinosa , Sertia mussotii, Sinoadina racemosa, Strychnos nux-vomica and Strychnos spinosa . Based on a literature review very few articles have been published on methyl (2R,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201012D          

 27 28  0  0  1  0            999 V2000
   -0.7145   -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  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  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  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    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
   -0.7145   -5.3625    0.0000 O   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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 11  1  6  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 13 22  1  6  0  0  0
  2 23  1  6  0  0  0
 23 24  2  0  0  0  0
  1 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END

     RDKit          3D

 51 52  0  0  0  0  0  0  0  0999 V2000
    1.2977    2.7284    1.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    1.8639    0.3389 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3725    0.3912    0.5329 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7194   -0.2976    0.3310 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7902    0.5960    0.9392 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5536    0.8528    2.3657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6694    0.3974    3.0314 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0093   -0.5452   -1.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2724   -1.2150   -1.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0862   -1.5935   -0.5956 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489   -1.4233   -2.8017 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7473   -2.0597   -3.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1870   -0.1799   -2.0517 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9866    0.4497   -1.7600 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3823   -0.0285   -0.5328 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8344    0.5637   -0.3158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8938   -0.3620   -0.1682 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8022   -0.2660   -1.1614 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0791    0.0363   -0.9079 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3181    1.5454   -1.0354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6542    1.8484   -0.7686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6791   -0.4795    0.3625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8552   -1.2045    0.1664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6598   -1.2839    1.1589 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1289   -1.6387    2.3888 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4538   -0.3430    1.2363 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5484   -0.7566    2.1740 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9204    2.3582    2.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4336    3.7979    1.1557 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9355    2.1968   -0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9602    0.1268    1.5048 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -1.2393    0.8904 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7617    0.1455    0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7588    1.5509    0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2585    1.5277    2.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989   -2.2517   -4.2483 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5940   -1.4156   -2.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8319   -3.0127   -2.6174 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4687   -0.3821   -3.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2445   -1.1121   -0.5366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3919   -1.3702   -0.2758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7099   -0.4045   -1.7399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1188    1.8712   -2.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7048    2.1140   -0.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9257    2.6202   -1.3211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9483    0.3866    1.0051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2993   -0.9786   -0.6888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4101   -2.1667    0.5640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8253   -1.1081    3.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8010    0.7120    1.4122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8513   -1.5623    2.6837 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15  3  1  0
  3  2  1  0
  2  1  2  3
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  4  8  1  0
 26 17  1  0
 12 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  0
 15 40  1  6
 17 41  1  6
 19 42  1  6
 20 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  1
 23 47  1  0
 24 48  1  6
 25 49  1  0
 26 50  1  1
 27 51  1  0
  3 31  1  1
  2 30  1  0
  1 28  1  0
  1 29  1  0
  4 32  1  1
  5 33  1  0
  5 34  1  0
  6 35  1  0
M  END


  Mrv1652304282201012D          

 27 28  0  0  1  0            999 V2000
   -0.7145   -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  2  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  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  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  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
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  1  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  2  0  0  0  0  0  0  0  0  0
   -2.1434   -5.3625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -6.1875    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
   -0.7145   -5.3625    0.0000 O   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
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    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  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 11  1  6  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  1  0  0  0
 18 19  1  0  0  0  0
 15 20  1  6  0  0  0
 14 21  1  1  0  0  0
 13 22  1  6  0  0  0
  2 23  1  6  0  0  0
 23 24  2  0  0  0  0
  1 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0051780

> <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

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16-,17+/m1/s1

> <INCHI_KEY>
CSKKDSFETGLMSB-FUJZYWHJSA-N

> <FORMULA>
C17H24O10

> <MOLECULAR_WEIGHT>
388.369

> <EXACT_MASS>
388.136946973

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.69529550644115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.83

> <JCHEM_LOGP>
-1.6899511996666665

> <ALOGPS_LOGS>
-1.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.187394981609977

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.205711973943044

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847615592584

> <JCHEM_POLAR_SURFACE_AREA>
151.98000000000002

> <JCHEM_REFRACTIVITY>
88.5206

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+01 g/l

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

> <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      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -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       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -0.000   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6   25                                                  
CONECT    2    1    3   23                                                  
CONECT    3    2    4   11                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9                                                            
CONECT   11    3   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15   21                                                  
CONECT   15   14   16   20                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16   12                                                       
CONECT   18   16   19                                                       
CONECT   19   18                                                            
CONECT   20   15                                                            
CONECT   21   14                                                            
CONECT   22   13                                                            
CONECT   23    2   24                                                       
CONECT   24   23                                                            
CONECT   25    1   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   56    0
END

View in JSmol

Synonyms

Value	Source
Methyl (2R,3R,4S)-3-ethenyl-4-(2-oxoethyl)-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₁₇H₂₄O₁₀

Average Mass

388.3690 Da

Monoisotopic Mass

388.13695 Da

IUPAC Name

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

Traditional Name

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

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

InChI Identifier

InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16-,17+/m1/s1

InChI Key

CSKKDSFETGLMSB-FUJZYWHJSA-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
Adina racemosa	Plant	KNApSAcK
Alangium lamarckii	Plant	KNApSAcK
Alangium salviifolium	Plant	KNApSAcK
Carapichea affinis	-	KNApSAcK
Catharanthus roseus	Plant	KNApSAcK
Centaurium erythraea	Plant	KNApSAcK
Cephaelis acuminata	Plant	KNApSAcK
Cornus officinalis	Plant	KNApSAcK
Laurencia dendroidea	-	KNApSAcK
Lippia graveolens	Plant	KNApSAcK
Lippia origanoides	LOTUS Database	35616633
Lonicera caerulea	LOTUS Database	35616633
Lonicera japonica	Plant	KNApSAcK
Lonicera morrowii	Plant	KNApSAcK
Lonicera periclymenum	LOTUS Database	35616633
Lonicera spp.	Plant	KNApSAcK
Mentzelia albescens	LOTUS Database	35616633
Ophiorrhiza pumila	Plant	KNApSAcK
Psychotria burucana	Plant	KNApSAcK
Psychotria ipecacuanha	Plant	KNApSAcK
Psychotria klugii	Plant	KNApSAcK
Rehmannia glutinosa	Plant	KNApSAcK
Sertia mussotii	-	KNApSAcK
Sinoadina racemosa	LOTUS Database	35616633
Strychnos nux-vomica L.	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
O-glycosyl compound
Secoiridoid-skeleton
Glycosyl compound
Monoterpenoid
Monocyclic monoterpenoid
Sugar acid
Oxane
Monosaccharide
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Alpha-hydrogen aldehyde
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Aldehyde
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	-0.83	ALOGPS
logP	-1.7	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	151.98 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	88.52 m³·mol⁻¹	ChemAxon
Polarizability	37.7 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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

124351303

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Secologanin (NP0051780)

MOL for NP0051780 (Secologanin)

3D MOL for NP0051780 (Secologanin)

3D SDF for NP0051780 (Secologanin)

3D-SDF for NP0051780 (Secologanin)

PDB for NP0051780 (Secologanin)

3D PDB for NP0051780 (Secologanin)

SMILES for NP0051780 (Secologanin)

INCHI for NP0051780 (Secologanin)

Structure for NP0051780 (Secologanin)

3D Structure for NP0051780 (Secologanin)