NP-MRD: Showing NP-Card for Lancerin (NP0051699)

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Record Information

Version

2.0

Created at

2022-04-27 22:58:05 UTC

Updated at

2022-04-27 22:58:05 UTC

NP-MRD ID

NP0051699

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lancerin

Description

Lancerin belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring. Lancerin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Lancerin is found in Gentiana utriculosa, Maclura cochinchinensis, Polygala caudata, Polygala sibirica , Polygala tenuifolia , Schultesia lisianthoides, Tripterospermum lanceolatum and Tripterospermum taiwanense. Lancerin was first documented in 2005 (PMID: 15974611). Based on a literature review a small amount of articles have been published on lancerin (PMID: 24702811) (PMID: 29997352) (PMID: 22006717) (PMID: 19296391).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282200582D          

 29 32  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    2.1434    2.0625    0.0000 O   0  0  0  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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  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   -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 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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 19 26  2  0  0  0  0
 24 27  1  0  0  0  0
  3 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END

     RDKit          3D

 47 50  0  0  0  0  0  0  0  0999 V2000
    4.3589   -1.9505    0.2992 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3835   -1.1838    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6043    0.1959    0.1902 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8723    0.6865    0.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0312    2.0549    0.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3198    2.5229    0.7161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9514    2.9023    0.2877 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6993    2.3779    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5077    0.9988   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2968    0.5049   -0.2378 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0539   -0.7846   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2389   -1.2268   -0.5613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3052   -0.2345   -0.6428 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8366   -0.0645    0.6915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522    1.1118    0.6706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7210    1.6944    2.0660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542    1.9463    2.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8956    0.8186    0.0403 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4113    1.9305   -0.6199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8251   -0.3380   -0.9170 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3251   -1.4802   -0.3250 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4655   -0.5337   -1.5278 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4497    0.4328   -2.6085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4367   -2.5691   -0.6281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6545   -3.1123   -0.8699 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386   -3.4653   -0.4409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8892   -3.0030   -0.1888 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -3.8609   -0.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1104   -1.6431   -0.1157 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7171    0.0095    0.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9629    2.7033   -0.0532 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1254    3.9804    0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8412    3.0228   -0.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9132    0.7661   -0.8950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0590    1.8897    0.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2950    2.6142    2.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1554    0.9029    2.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6067    2.4538    3.4293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5955    0.5588    0.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2034    2.3164   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5436   -0.1496   -1.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161   -1.7295    0.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4608   -1.4730   -2.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5664    0.8786   -2.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7871   -4.1087   -0.8969 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4599   -4.5175   -0.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7871   -4.8465   -0.0522 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 22  1  0
 22 23  1  0
 22 20  1  0
 20 21  1  0
 20 18  1  0
 18 19  1  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  8  2  0
  8  7  1  0
  7  5  2  0
  5  6  1  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 29  1  0
 29 27  2  0
 27 28  1  0
 27 26  1  0
 26 24  2  0
 24 25  1  0
 18 15  1  0
 24 12  1  0
 29 11  1  0
  3  9  1  0
 17 38  1  0
 16 36  1  0
 16 37  1  0
 15 35  1  6
 13 34  1  6
 22 43  1  6
 23 44  1  0
 20 41  1  6
 21 42  1  0
 18 39  1  1
 19 40  1  0
  8 33  1  0
  7 32  1  0
  6 31  1  0
  4 30  1  0
 28 47  1  0
 26 46  1  0
 25 45  1  0
M  END


  Mrv1652304282200582D          

 29 32  0  0  1  0            999 V2000
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    3.3000    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
    2.1434    2.0625    0.0000 O   0  0  0  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
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  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   -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 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
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
  7 13  1  0  0  0  0
 12 14  1  1  0  0  0
 14 15  1  0  0  0  0
  9 16  1  1  0  0  0
  8 17  1  6  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 20 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 19 26  2  0  0  0  0
 24 27  1  0  0  0  0
  3 28  1  0  0  0  0
  1 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051699

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC3=CC=C(O)C=C3C(=O)C2=C(O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O10/c20-5-11-15(25)16(26)17(27)19(29-11)13-9(23)4-8(22)12-14(24)7-3-6(21)1-2-10(7)28-18(12)13/h1-4,11,15-17,19-23,25-27H,5H2/t11-,15-,16+,17-,19+/m1/s1

> <INCHI_KEY>
JUZGXATTXYZBGK-HBVDJMOISA-N

> <FORMULA>
C19H18O10

> <MOLECULAR_WEIGHT>
406.343

> <EXACT_MASS>
406.08999678

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
38.51687307491018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3,7-trihydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9H-xanthen-9-one

> <ALOGPS_LOGP>
-0.14

> <JCHEM_LOGP>
-0.058376649666666336

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.779937542253103

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.139904957532055

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791926292654223

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
95.87729999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lancerin

> <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       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.668   8.470   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669   6.160   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6   29                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   28                                                  
CONECT    4    3    5   21                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   17                                                  
CONECT    9    8   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12    7                                                       
CONECT   14   12   15                                                       
CONECT   15   14                                                            
CONECT   16    9                                                            
CONECT   17    8                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21   23                                                  
CONECT   21   20    4   22                                                  
CONECT   22   21                                                            
CONECT   23   20   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25   19                                                       
CONECT   27   24                                                            
CONECT   28    3                                                            
CONECT   29    1                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

View in JSmol

Synonyms

Value	Source
4-C-Glucosyl-1,3,7-trihydroxyxanthone	ChEBI

Chemical Formula

C₁₉H₁₈O₁₀

Average Mass

406.3430 Da

Monoisotopic Mass

406.09000 Da

IUPAC Name

1,3,7-trihydroxy-4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-9H-xanthen-9-one

Traditional Name

lancerin

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC3=CC=C(O)C=C3C(=O)C2=C(O)C=C1O

InChI Identifier

InChI=1S/C19H18O10/c20-5-11-15(25)16(26)17(27)19(29-11)13-9(23)4-8(22)12-14(24)7-3-6(21)1-2-10(7)28-18(12)13/h1-4,11,15-17,19-23,25-27H,5H2/t11-,15-,16+,17-,19+/m1/s1

InChI Key

JUZGXATTXYZBGK-HBVDJMOISA-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
Gentiana utriculosa	LOTUS Database	35616633
Maclura cochinchinensis	LOTUS Database	35616633
Polygala caudata	Plant	KNApSAcK
Polygala sibirica	Plant	KNApSAcK
Polygala tenuifolia	Plant	KNApSAcK
Schultesia lisianthoides	LOTUS Database	35616633
Tripterospermum lanceolatum	Plant	KNApSAcK
Tripterospermum taiwanense	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Xanthones

Alternative Parents

Substituents

Phenolic glycoside
Xanthone
Hexose monosaccharide
C-glycosyl compound
Chromone
Glycosyl compound
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Oxane
Monosaccharide
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Oxacycle
Polyol
Dialkyl ether
Ether
Primary alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:6373 )
C-glycosyl compound (CHEBI:6373 )
xanthones (CHEBI:6373 )
xanthenes (C10075 )

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	-0.14	ALOGPS
logP	-0.058	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	95.88 m³·mol⁻¹	ChemAxon
Polarizability	38.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

C00002960

Chemspider ID

4444964

KEGG Compound ID

C10075

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281645

PDB ID

Not Available

ChEBI ID

6373

Good Scents ID

Not Available

References

General References

Zhou YH, Zhang SY, Guo Q, Chai XY, Jiang Y, Tu PF: Chemical investigation of the roots of Polygala sibirica L. Chin J Nat Med. 2014 Mar;12(3):225-8. doi: 10.1016/S1875-5364(14)60038-8. [PubMed:24702811 ]
Li X, Chen B, Zhao X, Chen D: 2-Phenyl-4,4,5,5-tetramethylimidazoline-1-oxyl 3-oxide Radical (PTIO*) Trapping Activity and Mechanisms of 16 Phenolic Xanthones. Molecules. 2018 Jul 11;23(7). pii: molecules23071692. doi: 10.3390/molecules23071692. [PubMed:29997352 ]
Xu M, Zhang M, Wang D, Yang CR, Zhang YJ: Phenolic compounds from the whole plants of Gentiana rhodantha (Gentianaceae). Chem Biodivers. 2011 Oct;8(10):1891-900. doi: 10.1002/cbdv.201000220. [PubMed:22006717 ]
Jankovic T, Krstic-Milosevic D, Aljancic I, Savikin K, Menkovic N, Radanovic D, Milosavljevic S: Phytochemical re-investigation of Gentiana utriculosa. Nat Prod Res. 2009;23(5):466-9. doi: 10.1080/14786410802079477. [PubMed:19296391 ]
Jiang Y, Zhang W, Tu P, Xu X: Xanthone glycosides from Polygala tenuifolia and their conformational analyses. J Nat Prod. 2005 Jun;68(6):875-9. doi: 10.1021/np050026+. [PubMed:15974611 ]

Showing NP-Card for Lancerin (NP0051699)

MOL for NP0051699 (Lancerin)

3D MOL for NP0051699 (Lancerin)

3D SDF for NP0051699 (Lancerin)

3D-SDF for NP0051699 (Lancerin)

PDB for NP0051699 (Lancerin)

3D PDB for NP0051699 (Lancerin)

SMILES for NP0051699 (Lancerin)

INCHI for NP0051699 (Lancerin)

Structure for NP0051699 (Lancerin)

3D Structure for NP0051699 (Lancerin)