NP-MRD: Showing NP-Card for 3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid (NP0269419)

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Record Information

Version

2.0

Created at

2022-09-08 14:53:43 UTC

Updated at

2022-09-08 14:53:44 UTC

NP-MRD ID

NP0269419

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid

Description

3-Epipapyriferic acid, also known as 3-epipapyriferate, 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. 3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid is found in Betula glandulosa, Betula pendula and Betula platyphylla. 3-Epipapyriferic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061311532D          

 43 47  0  0  0  0            999 V2000
    2.7885    2.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -1.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5378   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5388    4.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9555    3.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7863    1.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3269   -0.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644    2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    1.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979   -1.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562    0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2772    2.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7134    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7244    2.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    1.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0728    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035    3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0690   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2023    4.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7889   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4490    4.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    2.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    3.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 20  1  1  0  0  0  0
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 26 13  1  0  0  0  0
 27 19  1  0  0  0  0
 28 19  1  0  0  0  0
 29 21  1  0  0  0  0
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 30  2  1  0  0  0  0
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 31 26  1  0  0  0  0
 32  6  1  0  0  0  0
 32 14  1  0  0  0  0
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 32 24  1  0  0  0  0
 33  7  1  0  0  0  0
 33 16  1  0  0  0  0
 33 24  1  0  0  0  0
 34  8  1  0  0  0  0
 34 15  1  0  0  0  0
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 34 33  1  0  0  0  0
 35  9  1  0  0  0  0
 35 17  1  0  0  0  0
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 37 27  2  0  0  0  0
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 42 25  1  0  0  0  0
 42 28  1  0  0  0  0
 43 26  1  0  0  0  0
 43 35  1  0  0  0  0
M  END

     RDKit          3D

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 36 89  1  0
 36 90  1  0
 37 91  1  1
 39 92  1  0
 39 93  1  0
 39 94  1  0
 40 95  1  0
 40 96  1  0
 40 97  1  0
 41 98  1  0
M  END


  Mrv0541 05061311532D          

 43 47  0  0  0  0            999 V2000
    2.7885    2.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -1.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5378   -1.6661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5388    4.9717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9555    3.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7863    1.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6252   -0.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3269   -0.0575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1644    2.6471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1992    1.0221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4979   -1.0368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3562    0.2036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2772    2.7502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712    0.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7134    0.3553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2129   -0.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7244    2.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5012    1.4382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0728    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5035    3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7151    1.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2162    1.8497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7840   -0.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5001    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3551   -0.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8657    3.4652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7867    0.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0739   -0.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9302    1.4363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0690   -1.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2023    4.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7851    0.2016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9291    0.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9712    2.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5046    3.9132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855    1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5017    0.2074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7889   -1.0310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4490    4.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2174    2.6747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6401   -1.0329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0585    3.2948    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 13  1  0  0  0  0
 20  1  1  0  0  0  0
 21 10  1  0  0  0  0
 22 18  1  0  0  0  0
 23 11  1  0  0  0  0
 24 18  1  0  0  0  0
 25 12  1  0  0  0  0
 26 13  1  0  0  0  0
 27 19  1  0  0  0  0
 28 19  1  0  0  0  0
 29 21  1  0  0  0  0
 29 22  1  0  0  0  0
 30  2  1  0  0  0  0
 30  3  1  0  0  0  0
 30 23  1  0  0  0  0
 30 25  1  0  0  0  0
 31  4  1  0  0  0  0
 31  5  1  0  0  0  0
 31 26  1  0  0  0  0
 32  6  1  0  0  0  0
 32 14  1  0  0  0  0
 32 23  1  0  0  0  0
 32 24  1  0  0  0  0
 33  7  1  0  0  0  0
 33 16  1  0  0  0  0
 33 24  1  0  0  0  0
 34  8  1  0  0  0  0
 34 15  1  0  0  0  0
 34 29  1  0  0  0  0
 34 33  1  0  0  0  0
 35  9  1  0  0  0  0
 35 17  1  0  0  0  0
 35 21  1  0  0  0  0
 36 20  2  0  0  0  0
 37 27  2  0  0  0  0
 38 27  1  0  0  0  0
 39 28  2  0  0  0  0
 40 31  1  0  0  0  0
 41 20  1  0  0  0  0
 41 22  1  0  0  0  0
 42 25  1  0  0  0  0
 42 28  1  0  0  0  0
 43 26  1  0  0  0  0
 43 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269419

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(O)=O)C(C)(C)C3CCC2(C)C2(C)CCC(C12)C1(C)CCC(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)

> <INCHI_KEY>
RLVAVWQAAQFUOP-UHFFFAOYSA-N

> <FORMULA>
C35H56O8

> <MOLECULAR_WEIGHT>
604.8143

> <EXACT_MASS>
604.397518768

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
68.42501354678676

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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>
119.36000000000001

> <JCHEM_REFRACTIVITY>
160.7205

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.205   4.997   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.850  -3.113   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.871  -3.110   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.072   9.281   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.850   7.246   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.201   1.916   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.634  -0.778   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.944  -0.107   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.640   4.941   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.572   1.908   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.529  -1.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.532   0.380   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.584   5.134   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.866   1.148   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.665   0.663   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.864  -1.167   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.552   3.991   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.536   2.685   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.136   0.384   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.540   5.765   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.668   3.155   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.870   3.453   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.197  -1.163   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.534   1.144   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.530  -1.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.816   6.468   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.469   1.155   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.138  -1.156   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       9.203   2.681   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       3.862  -1.932   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.444   7.874   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.199   0.376   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       7.866   0.373   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.201   1.141   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      11.146   4.619   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.542   7.305   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -1.466   2.695   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.803   0.387   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -1.473  -1.925   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      12.038   8.503   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       7.872   4.993   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       1.195  -1.928   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      11.309   6.150   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   30                                                            
CONECT    3   30                                                            
CONECT    4   31                                                            
CONECT    5   31                                                            
CONECT    6   32                                                            
CONECT    7   33                                                            
CONECT    8   34                                                            
CONECT    9   35                                                            
CONECT   10   15   21                                                       
CONECT   11   16   23                                                       
CONECT   12   14   25                                                       
CONECT   13   17   26                                                       
CONECT   14   12   32                                                       
CONECT   15   10   34                                                       
CONECT   16   11   33                                                       
CONECT   17   13   35                                                       
CONECT   18   22   24                                                       
CONECT   19   27   28                                                       
CONECT   20    1   36   41                                                  
CONECT   21   10   29   35                                                  
CONECT   22   18   29   41                                                  
CONECT   23   11   30   32                                                  
CONECT   24   18   32   33                                                  
CONECT   25   12   30   42                                                  
CONECT   26   13   31   43                                                  
CONECT   27   19   37   38                                                  
CONECT   28   19   39   42                                                  
CONECT   29   21   22   34                                                  
CONECT   30    2    3   23   25                                             
CONECT   31    4    5   26   40                                             
CONECT   32    6   14   23   24                                             
CONECT   33    7   16   24   34                                             
CONECT   34    8   15   29   33                                             
CONECT   35    9   17   21   43                                             
CONECT   36   20                                                            
CONECT   37   27                                                            
CONECT   38   27                                                            
CONECT   39   28                                                            
CONECT   40   31                                                            
CONECT   41   20   22                                                       
CONECT   42   25   28                                                       
CONECT   43   26   35                                                       
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
3-Epipapyriferate	Generator
[2,2']Bi[1,3,4,9-tetrathia-cyclopenta[b]naphthalenylidene]	HMDB
3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoate	Generator

Chemical Formula

C₃₅H₅₆O₈

Average Mass

604.8143 Da

Monoisotopic Mass

604.39752 Da

IUPAC Name

3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoic acid

Traditional Name

3-{[16-(acetyloxy)-14-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2C3(C)CCC(OC(=O)CC(O)=O)C(C)(C)C3CCC2(C)C2(C)CCC(C12)C1(C)CCC(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)

InChI Key

RLVAVWQAAQFUOP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

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

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Betula glandulosa	LOTUS Database	35616633
Betula pendula	LOTUS Database	35616633
Betula platyphylla	LOTUS Database	35616633

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
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

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	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	68.43 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

HMDB0040498

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020261

KNApSAcK ID

Not Available

Chemspider ID

511579

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

588518

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid (NP0269419)

MOL for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

3D MOL for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

3D SDF for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

3D-SDF for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

PDB for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

3D PDB for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

SMILES for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

INCHI for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

Structure for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)

3D Structure for NP0269419 (3-{[11-(acetyloxy)-1-[5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]-3a,3b,6,6,9a-pentamethyl-dodecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxy}-3-oxopropanoic acid)