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Showing NP-Card for 24-Hydroxyglycyrrhetic acid (NP0335113)

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Record Information
Version2.0
Created at2024-09-10 23:56:47 UTC
Updated at2024-09-10 23:56:47 UTC
NP-MRD IDNP0335113
Secondary Accession NumbersNone
Natural Product Identification
Common Name24-Hydroxyglycyrrhetic acid
Description24-Hydroxyglycyrrhetic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 24-Hydroxyglycyrrhetic acid was first documented in 2021 (PMID: 33931765). Based on a literature review very few articles have been published on 24-Hydroxyglycyrrhetic acid.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0335113 (24-Hydroxyglycyrrhetic acid)


  Mrv2104 05262302292D          

 35 39  0  0  0  0            999 V2000
   -2.7591   -1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7591   -2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439   -2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300   -2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300   -1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115    0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    0.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148    0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -1.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242    0.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    0.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    1.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242    1.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    2.4145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    3.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9520   -0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300    0.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115   -1.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300   -0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -2.4146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573   -3.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304   -3.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843   -3.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 32  1  0  0  0  0
  3  4  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 31  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
  9 11  1  0  0  0  0
  9 30  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 29  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 28  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 27  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
Download

3D MOL for NP0335113 (24-Hydroxyglycyrrhetic acid)

Download
3D SDF for NP0335113 (24-Hydroxyglycyrrhetic acid)

  Mrv2104 05262302292D          

 35 39  0  0  0  0            999 V2000
   -2.7591   -1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7591   -2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439   -2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300   -2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300   -1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -2.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -2.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115    0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992    0.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6148    0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242   -1.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353   -0.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    0.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242    0.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    0.4699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9451    1.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    1.6978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5242    1.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8219    2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6488    2.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4758    2.4145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2353    3.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9520   -0.3528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300    0.4742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8115   -1.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3300   -0.3473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4758   -2.4146    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4573   -3.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6304   -3.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2843   -3.1313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2 32  1  0  0  0  0
  3  4  1  0  0  0  0
  3 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 31  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
  9 11  1  0  0  0  0
  9 30  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 29  1  0  0  0  0
 12 13  2  0  0  0  0
 12 18  1  0  0  0  0
 13 14  1  0  0  0  0
 14 28  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 27  1  0  0  0  0
 18 22  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
 33 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC(C)(CC1C1=CC(=O)C3C4(C)CCC(O)C(C)(CO)C4CCC3(C)C1(C)CC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C30H46O5/c1-25-11-12-26(2,24(34)35)16-19(25)18-15-20(32)23-27(3)9-8-22(33)28(4,17-31)21(27)7-10-30(23,6)29(18,5)14-13-25/h15,19,21-23,31,33H,7-14,16-17H2,1-6H3,(H,34,35)

> <INCHI_KEY>
GSEPOEIKWTXTHS-UHFFFAOYNA-N

> <FORMULA>
C30H46O5

> <MOLECULAR_WEIGHT>
486.693

> <EXACT_MASS>
486.334524581

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.37622178394868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid

> <JCHEM_LOGP>
4.750556879666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.4858992547784

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.444329599256007

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7854502911899646

> <JCHEM_POLAR_SURFACE_AREA>
94.83

> <JCHEM_REFRACTIVITY>
136.04319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0335113 (24-Hydroxyglycyrrhetic acid)
Download
PDB for NP0335113 (24-Hydroxyglycyrrhetic acid)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -5.150  -2.192   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.150  -3.735   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.815  -4.507   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.483  -3.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.483  -2.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.815  -1.423   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.148  -4.507   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.185  -3.735   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.185  -2.192   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.148  -1.423   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.515  -1.423   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.515   0.113   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.185   0.880   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.148   0.113   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.845  -2.189   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.173  -1.423   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.173   0.113   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.845   0.877   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.498   0.877   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.498   2.408   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.173   3.169   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.845   2.408   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.401   4.507   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.944   4.507   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.488   4.507   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.173   5.845   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       5.510  -0.659   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.483   0.885   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.515  -2.966   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.185  -0.648   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.483  -0.648   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.488  -4.507   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.587  -5.845   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.043  -5.845   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -6.131  -5.845   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   32                                                  
CONECT    3    2    4   33   34                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   31                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11   30                                             
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   29                                             
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   10   13   28                                                  
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   27                                             
CONECT   18   12   17   22                                                  
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23   24                                             
CONECT   22   18   21                                                       
CONECT   23   21                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
CONECT   27   17                                                            
CONECT   28   14                                                            
CONECT   29   11                                                            
CONECT   30    9                                                            
CONECT   31    5                                                            
CONECT   32    2                                                            
CONECT   33    3   35                                                       
CONECT   34    3                                                            
CONECT   35   33                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

Download
3D PDB for NP0335113 (24-Hydroxyglycyrrhetic acid)
Download
SMILES for NP0335113 (24-Hydroxyglycyrrhetic acid)
CC12CCC(C)(CC1C1=CC(=O)C3C4(C)CCC(O)C(C)(CO)C4CCC3(C)C1(C)CC2)C(O)=O
Download
INCHI for NP0335113 (24-Hydroxyglycyrrhetic acid)
InChI=1/C30H46O5/c1-25-11-12-26(2,24(34)35)16-19(25)18-15-20(32)23-27(3)9-8-22(33)28(4,17-31)21(27)7-10-30(23,6)29(18,5)14-13-25/h15,19,21-23,31,33H,7-14,16-17H2,1-6H3,(H,34,35)
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View in JSmol
Synonyms
ValueSource
24-HydroxyglycyrrhetateGenerator
Chemical FormulaC30H46O5
Average Mass486.6930 Da
Monoisotopic Mass486.33452 Da
IUPAC Name10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid
Traditional Name10-hydroxy-9-(hydroxymethyl)-2,4a,6a,6b,9,12a-hexamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC12CCC(C)(CC1C1=CC(=O)C3C4(C)CCC(O)C(C)(CO)C4CCC3(C)C1(C)CC2)C(O)=O
InChI Identifier
InChI=1/C30H46O5/c1-25-11-12-26(2,24(34)35)16-19(25)18-15-20(32)23-27(3)9-8-22(33)28(4,17-31)21(27)7-10-30(23,6)29(18,5)14-13-25/h15,19,21-23,31,33H,7-14,16-17H2,1-6H3,(H,34,35)
InChI KeyGSEPOEIKWTXTHS-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound 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
    • 

  • Cyclohexenone
    • 

  • Cyclic alcohol
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP4.75ChemAxon
pKa (Strongest Acidic)4.44ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity136.04 m³·mol⁻¹ChemAxon
Polarizability56.38 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Lan XF, Olaleye OE, Lu JL, Yang W, Du FF, Yang JL, Cheng C, Shi YH, Wang FQ, Zeng XS, Tian NN, Liao PW, Yu X, Xu F, Li YF, Wang HT, Zhang NX, Jia WW, Li C: Pharmacokinetics-based identification of pseudoaldosterogenic compounds originating from Glycyrrhiza uralensis roots (Gancao) after dosing LianhuaQingwen capsule. Acta Pharmacol Sin. 2021 Dec;42(12):2155-2172. doi: 10.1038/s41401-021-00651-2.  Epub 2021 Apr 30. [PubMed:33931765  ]