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Showing NP-Card for Soyasapogenol E (NP0048036)

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Record Information
Version1.0
Created at2022-03-17 20:50:03 UTC
Updated at2022-03-17 20:50:03 UTC
NP-MRD IDNP0048036
Secondary Accession NumbersNone
Natural Product Identification
Common NameSoyasapogenol E
DescriptionSoyasapogenol E belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Soyasapogenol E is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Soyasapogenol E has been detected, but not quantified in, several different foods, such as swiss chards, triticales, bitter gourds, canada blueberries, and red algaes. Soyasapogenol E is found in Medicago sativa , Medicago truncatula, Melilotus messanensis and Oxytropis falcata. It was first documented in 2000 (PMID: 11413487). This could make soyasapogenol e a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048036 (Soyasapogenol E)


  Mrv0541 05061307592D          

 33 37  0  0  0  0            999 V2000
    4.6207   -1.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6813   -1.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654   -4.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -4.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -7.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -3.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2931   -4.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2931   -6.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -5.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -4.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -6.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510   -4.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -5.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8655   -2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -7.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -4.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -3.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787   -6.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2931   -4.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -6.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8655   -3.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510   -2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510   -4.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -5.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -6.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -4.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160   -8.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648   -6.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5799   -4.1186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -5.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127   -4.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 13 12  1  0  0  0  0
 17  6  2  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
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 22 15  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24  3  1  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26  5  1  0  0  0  0
 26 16  1  0  0  0  0
 26 19  1  0  0  0  0
 26 21  1  0  0  0  0
 27 13  1  0  0  0  0
 27 17  1  0  0  0  0
 28 11  1  0  0  0  0
 28 20  1  0  0  0  0
 28 27  1  0  0  0  0
 29 16  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  2  0  0  0  0
 27 32  1  0  0  0  0
 28 33  1  0  0  0  0
M  END
Download

3D MOL for NP0048036 (Soyasapogenol E)

Download
3D SDF for NP0048036 (Soyasapogenol E)

  Mrv0541 05061307592D          

 33 37  0  0  0  0            999 V2000
    4.6207   -1.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6813   -1.8367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8654   -4.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -4.5311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3944   -7.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -3.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2931   -4.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2931   -6.5936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -5.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -4.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -6.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510   -4.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -5.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8655   -2.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -7.2256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -4.1186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4365   -3.7061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5787   -6.1812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2931   -4.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1497   -6.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8655   -3.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510   -2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1510   -4.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786   -5.3561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8642   -6.5937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -4.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0076   -5.3562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6160   -8.0009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5648   -6.5936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5799   -4.1186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7221   -5.7687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0127   -4.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  8  1  0  0  0  0
 13 12  1  0  0  0  0
 17  6  2  0  0  0  0
 18 14  1  0  0  0  0
 18 17  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 21  9  1  0  0  0  0
 22 15  1  0  0  0  0
 23  1  1  0  0  0  0
 23  2  1  0  0  0  0
 23 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24  3  1  0  0  0  0
 24 12  1  0  0  0  0
 24 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25  4  1  0  0  0  0
 25 10  1  0  0  0  0
 25 19  1  0  0  0  0
 25 20  1  0  0  0  0
 26  5  1  0  0  0  0
 26 16  1  0  0  0  0
 26 19  1  0  0  0  0
 26 21  1  0  0  0  0
 27 13  1  0  0  0  0
 27 17  1  0  0  0  0
 28 11  1  0  0  0  0
 28 20  1  0  0  0  0
 28 27  1  0  0  0  0
 29 16  1  0  0  0  0
 30 21  1  0  0  0  0
 31 22  2  0  0  0  0
 27 32  1  0  0  0  0
 28 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048036

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(CO)C5CCC4(C)C3(C)CCC2(C)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-23,31-32H,9-18H2,1-7H3

> <INCHI_KEY>
FNRBOAGVUNHDIL-UHFFFAOYSA-N

> <FORMULA>
C30H48O3

> <MOLECULAR_WEIGHT>
456.7003

> <EXACT_MASS>
456.360345402

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
55.2864823847597

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-hydroxy-9-(hydroxymethyl)-2,2,4a,6a,6b,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicen-4-one

> <ALOGPS_LOGP>
6.05

> <JCHEM_LOGP>
5.4550863163333325

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.270342745780184

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.485961382940463

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7854425934406057

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
134.37519999999992

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.74e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-9-(hydroxymethyl)-2,2,4a,6a,6b,9,12a-heptamethyl-3,5,6,7,8,8a,10,11,12,12b,13,14b-dodecahydro-1H-picen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048036 (Soyasapogenol E)
Download
PDB for NP0048036 (Soyasapogenol E)
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       8.625  -3.429   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.605  -3.429   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.949  -8.458   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.947  -8.458   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.603 -13.488   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.614  -6.918   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.280  -7.688   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.280 -12.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.279  -9.998   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.613  -9.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.614 -11.538   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.615  -9.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.281  -9.998   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.281  -5.378   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.949  -5.378   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.623 -13.488   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.948  -7.688   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.281  -6.918   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.947 -11.538   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.280  -9.228   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.279 -11.538   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.949  -6.918   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.615  -4.608   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.615  -7.688   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.947  -9.998   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.613 -12.308   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.948  -9.228   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.614  -9.998   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.150 -14.935   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -1.054 -12.308   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      12.282  -7.688   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.948 -10.768   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.624  -8.458   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   23                                                            
CONECT    3   24                                                            
CONECT    4   25                                                            
CONECT    5   26                                                            
CONECT    6    7   17                                                       
CONECT    7    6   20                                                       
CONECT    8   11   19                                                       
CONECT    9   10   21                                                       
CONECT   10    9   25                                                       
CONECT   11    8   28                                                       
CONECT   12   13   24                                                       
CONECT   13   12   27                                                       
CONECT   14   18   23                                                       
CONECT   15   22   23                                                       
CONECT   16   26   29                                                       
CONECT   17    6   18   27                                                  
CONECT   18   14   17   24                                                  
CONECT   19    8   25   26                                                  
CONECT   20    7   25   28                                                  
CONECT   21    9   26   30                                                  
CONECT   22   15   24   31                                                  
CONECT   23    1    2   14   15                                             
CONECT   24    3   12   18   22                                             
CONECT   25    4   10   19   20                                             
CONECT   26    5   16   19   21                                             
CONECT   27   13   17   28   32                                             
CONECT   28   11   20   27   33                                             
CONECT   29   16                                                            
CONECT   30   21                                                            
CONECT   31   22                                                            
CONECT   32   27                                                            
CONECT   33   28                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   74    0
END

Download
3D PDB for NP0048036 (Soyasapogenol E)
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SMILES for NP0048036 (Soyasapogenol E)
CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(CO)C5CCC4(C)C3(C)CCC2(C)C(=O)C1
Download
INCHI for NP0048036 (Soyasapogenol E)
InChI=1S/C30H48O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-23,31-32H,9-18H2,1-7H3
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View in JSmol
Synonyms
ValueSource
3,23-Dihydroxy-(3beta,4beta)-olean-12-en-22-oneHMDB
3,24-Dihydroxy-12-oleanen-22-oneHMDB
Chemical FormulaC30H48O3
Average Mass456.7003 Da
Monoisotopic Mass456.36035 Da
IUPAC Name10-hydroxy-9-(hydroxymethyl)-2,2,4a,6a,6b,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicen-4-one
Traditional Name10-hydroxy-9-(hydroxymethyl)-2,2,4a,6a,6b,9,12a-heptamethyl-3,5,6,7,8,8a,10,11,12,12b,13,14b-dodecahydro-1H-picen-4-one
CAS Registry Number6750-59-0
SMILES
CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(CO)C5CCC4(C)C3(C)CCC2(C)C(=O)C1
InChI Identifier
InChI=1S/C30H48O3/c1-25(2)16-20-19-8-9-22-27(4)12-11-23(32)28(5,18-31)21(27)10-13-30(22,7)29(19,6)15-14-26(20,3)24(33)17-25/h8,20-23,31-32H,9-18H2,1-7H3
InChI KeyFNRBOAGVUNHDIL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Glycine maxFooDB
Medicago sativaPlant
Medicago truncatulaPlant
Melilotus messanensisPlant
Oxytropis falcataLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassTriterpenoids  
Direct ParentTriterpenoids  
Alternative Parents
Substituents
  • Triterpenoid
    • 

  • Steroid
    • 

  • Cyclic alcohol
    • 

  • Secondary alcohol
    • 

  • Ketone
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Primary alcohol
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.05ALOGPS
logP5.46ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)14.49ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity134.38 m³·mol⁻¹ChemAxon
Polarizability55.29 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034652  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB013176  
KNApSAcK IDNot Available
Chemspider ID16100549  
KEGG Compound IDC17420  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13632870  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487  ] 
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246  ] 
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880  ] 
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567  ]