NP-MRD: Showing NP-Card for Papyriferic acid (NP0052220)

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Record Information

Version

2.0

Created at

2022-04-27 23:21:35 UTC

Updated at

2022-04-27 23:21:35 UTC

NP-MRD ID

NP0052220

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Papyriferic acid

Description

PAPYRIFERIC ACID, also known as papyriferate, belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. Papyriferic acid is found in Betula fruticosa, Betula glandulosa, Betula nana, Betula papyrifera, Betula pendula, Betula platyphylla and Betula resinifera. Papyriferic acid was first documented in 2002 (PMID: 12464579). Based on a literature review a small amount of articles have been published on PAPYRIFERIC ACID (PMID: 22116690) (PMID: 20363142) (PMID: 19838755).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201212D          

 43 47  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    3.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    4.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9702    4.9171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626    3.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2883    2.9282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5247   -0.6098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1808   -1.0953    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
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 16 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 19 22  1  6  0  0  0
 22 23  1  0  0  0  0
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 27 30  1  0  0  0  0
 22 31  1  6  0  0  0
 11 32  1  1  0  0  0
  8 33  1  6  0  0  0
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  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  2 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END

     RDKit          3D

 99103  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652304282201212D          

 43 47  0  0  1  0            999 V2000
    4.2475    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.3777    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.9960    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    0.8922    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9035    1.6682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4354    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.8134    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5596    1.1827    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8399    0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    0.2615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.3279    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4672    2.1038    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9990    2.7345    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8111    2.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7187    3.5104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2505    4.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9702    4.9171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0626    3.9959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    2.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5867    1.2845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    0.8215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    2.7283    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2236    3.4707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0408    3.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1861    2.5457    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4586    2.1567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9284    2.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6708    1.8260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2883    2.9282    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5686    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630    3.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    0.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487    0.4185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    2.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6077    0.1935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -0.0697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.2325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6202    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0884   -0.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4323    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7126   -0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5247   -0.6098    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1808   -1.0953    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
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  6  0  0  0
  8 11  1  0  0  0  0
 12 11  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  7 14  1  6  0  0  0
 13 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 19 22  1  6  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 22 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 22 31  1  6  0  0  0
 11 32  1  1  0  0  0
  8 33  1  6  0  0  0
  5 34  1  6  0  0  0
  3 35  1  0  0  0  0
  3 36  1  0  0  0  0
  2 37  1  1  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  2  0  0  0  0
 41 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052220

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@@H](OC(=O)CC(O)=O)C(C)(C)[C@@H]3CC[C@@]2(C)[C@]2(C)CC[C@@H]([C@@H]12)[C@]1(C)CC[C@@H](O1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C35H56O8/c1-20(36)41-22-18-24-32(6)14-12-25(42-28(39)19-27(37)38)30(2,3)23(32)11-16-33(24,7)34(8)15-10-21(29(22)34)35(9)17-13-26(43-35)31(4,5)40/h21-26,29,40H,10-19H2,1-9H3,(H,37,38)/t21-,22+,23-,24+,25+,26+,29-,32-,33+,34+,35-/m0/s1

> <INCHI_KEY>
RLVAVWQAAQFUOP-GNYBQDBLSA-N

> <FORMULA>
C35H56O8

> <MOLECULAR_WEIGHT>
604.825

> <EXACT_MASS>
604.397518763

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
68.50033501159157

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[(1R,2R,5R,7R,10R,11R,14S,15R,16R)-16-(acetyloxy)-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3-oxopropanoic acid

> <ALOGPS_LOGP>
5.82

> <JCHEM_LOGP>
5.327681833333331

> <ALOGPS_LOGS>
-6.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.325328775704747

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.29453936317829

> <JCHEM_PKA_STRONGEST_BASIC>
-3.09390119352444

> <JCHEM_POLAR_SURFACE_AREA>
119.36

> <JCHEM_REFRACTIVITY>
160.7205000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[(1R,2R,5R,7R,10R,11R,14S,15R,16R)-16-(acetyloxy)-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3-oxopropanoic 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       7.929   4.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.452   2.572   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.459   1.394   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.943   1.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.420   3.114   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.413   4.291   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.904   3.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.911   2.208   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.434   0.759   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.950   0.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.395   2.479   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.872   3.927   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.865   5.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.381   4.833   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.342   6.553   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.334   7.730   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.811   9.179   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       3.850   7.459   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.667   3.877   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.095   2.398   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.179   1.534   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.612   5.093   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.284   6.479   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.810   6.268   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.081   4.752   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.723   4.026   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.466   4.080   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -6.852   3.409   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -6.138   5.466   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.795   2.695   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.304   5.906   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.764   0.984   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.331   0.781   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.897   4.562   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.601   0.361   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.241  -0.130   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       9.968   2.301   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      10.491   0.852   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       9.498  -0.325   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      12.007   0.581   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      12.530  -0.867   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      14.046  -1.138   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      11.538  -2.044   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   37                                                  
CONECT    3    2    4   35   36                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   34                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   33                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   21   32                                             
CONECT   12   11   13   19                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   12   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20   11                                                       
CONECT   22   19   23   26   31                                             
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25   22                                                       
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27                                                            
CONECT   31   22                                                            
CONECT   32   11                                                            
CONECT   33    8                                                            
CONECT   34    5                                                            
CONECT   35    3                                                            
CONECT   36    3                                                            
CONECT   37    2   38                                                       
CONECT   38   37   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
PAPYRIFERate	Generator

Chemical Formula

C₃₅H₅₆O₈

Average Mass

604.8250 Da

Monoisotopic Mass

604.39752 Da

IUPAC Name

3-{[(1R,2R,5R,7R,10R,11R,14S,15R,16R)-16-(acetyloxy)-14-[(2S,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-5-yl]oxy}-3-oxopropanoic acid

Traditional Name

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@@H]2[C@@]3(C)CC[C@@H](OC(=O)CC(O)=O)C(C)(C)[C@@H]3CC[C@@]2(C)[C@]2(C)CC[C@@H]([C@@H]12)[C@]1(C)CC[C@@H](O1)C(C)(C)O

InChI Identifier

InChI=1S/C35H56O8/c1-20(36)41-22-18-24-32(6)14-12-25(42-28(39)19-27(37)38)30(2,3)23(32)11-16-33(24,7)34(8)15-10-21(29(22)34)35(9)17-13-26(43-35)31(4,5)40/h21-26,29,40H,10-19H2,1-9H3,(H,37,38)/t21-,22+,23-,24+,25+,26+,29-,32-,33+,34+,35-/m0/s1

InChI Key

RLVAVWQAAQFUOP-GNYBQDBLSA-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
Betula fruticosa	LOTUS Database	35616633
Betula glandulosa	LOTUS Database	35616633
Betula nana	LOTUS Database	35616633
Betula papyrifera	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Betula platyphylla	LOTUS Database	35616633
Betula resinifera	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Steroid ester
14-alpha-methylsteroid
Steroid
Tricarboxylic acid or derivatives
1,3-dicarbonyl compound
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

triterpenoid saponin (CHEBI:7919 )
Dammarenes (C08632 )

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	5.82	ALOGPS
logP	5.33	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	160.72 m³·mol⁻¹	ChemAxon
Polarizability	68.5 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003752

Chemspider ID

390296

KEGG Compound ID

C08632

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

441683

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Forbey JS, Pu X, Xu D, Kielland K, Bryant J: Inhibition of snowshoe hare succinate dehydrogenase activity as a mechanism of deterrence for papyriferic acid in birch. J Chem Ecol. 2011 Dec;37(12):1285-93. doi: 10.1007/s10886-011-0039-9. Epub 2011 Nov 25. [PubMed:22116690 ]
Xiong J, Taniguchi M, Kashiwada Y, Sekiya M, Yamagishi T, Takaishi Y: Papyriferic acid derivatives as reversal agents of multidrug resistance in cancer cells. Bioorg Med Chem. 2010 Apr 15;18(8):2964-75. doi: 10.1016/j.bmc.2010.02.046. Epub 2010 Mar 6. [PubMed:20363142 ]
McLean S, Richards SM, Cover SL, Brandon S, Davies NW, Bryant JP, Clausen TP: Papyriferic acid, an antifeedant triterpene from birch trees, inhibits succinate dehydrogenase from liver mitochondria. J Chem Ecol. 2009 Oct;35(10):1252-61. doi: 10.1007/s10886-009-9702-9. Epub 2009 Oct 17. [PubMed:19838755 ]
Tegelberg R, Aphalo PJ, Julkunen-Tiitto R: Effects of long-term, elevated ultraviolet-B radiation on phytochemicals in the bark of silver birch (Betula pendula). Tree Physiol. 2002 Dec;22(17):1257-63. doi: 10.1093/treephys/22.17.1257. [PubMed:12464579 ]

Showing NP-Card for Papyriferic acid (NP0052220)

MOL for NP0052220 (Papyriferic acid)

3D MOL for NP0052220 (Papyriferic acid)

3D SDF for NP0052220 (Papyriferic acid)

3D-SDF for NP0052220 (Papyriferic acid)

PDB for NP0052220 (Papyriferic acid)

3D PDB for NP0052220 (Papyriferic acid)

SMILES for NP0052220 (Papyriferic acid)

INCHI for NP0052220 (Papyriferic acid)

Structure for NP0052220 (Papyriferic acid)

3D Structure for NP0052220 (Papyriferic acid)