NP-MRD: Showing NP-Card for Glyuranolide (NP0086435)

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Record Information

Version

2.0

Created at

2022-04-29 06:44:26 UTC

Updated at

2022-04-29 06:44:26 UTC

NP-MRD ID

NP0086435

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glyuranolide

Description

Methyl (1S,2R,5R,6R,9R,11S,14S,15R,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]Tetracos-17-ene-5-carboxylate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Glyuranolide is found in Glycyrrhiza uralensis . Based on a literature review very few articles have been published on methyl (1S,2R,5R,6R,9R,11S,14S,15R,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]Tetracos-17-ene-5-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208442D          

 40 45  0  0  1  0            999 V2000
    8.5597    0.1563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7348    0.1725    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.3364    0.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1170    1.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2091    1.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5116    0.9111    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.6867    0.9273    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1132    1.6335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2883    1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8619    0.9434    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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    4.4354    0.2372    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4835   -0.5176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3084   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
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  9 10  1  0  0  0  0
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  6 13  1  0  0  0  0
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 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
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 30 38  1  1  0  0  0
 36 39  1  0  0  0  0
 31 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292208442D          

 40 45  0  0  1  0            999 V2000
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    4.4915    3.0945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1403    2.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386    1.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8138    1.6982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3874    0.9920    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5741    1.1309    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9585    0.5817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    1.7422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858    0.2696    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9620    0.2240    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -0.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764   -0.7200    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5375   -1.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3939    0.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0040   -0.2420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2816   -0.6404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 10 17  1  1  0  0  0
 10 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 21 22  2  0  0  0  0
 18 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 23 26  2  0  0  0  0
 18 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  1  1  0  0  0
 29 33  1  0  0  0  0
 19 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
 30 38  1  1  0  0  0
 36 39  1  0  0  0  0
 31 39  1  0  0  0  0
 39 40  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086435

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@]3(C)C[C@H](OC3=O)[C@]1(C)CC[C@]1(C(=O)OC)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C31H44O6/c1-26(2)20-8-11-30(6)23(29(20,5)10-9-21(26)33)19(32)14-17-18-15-27(3)16-22(37-24(27)34)28(18,4)12-13-31(17,30)25(35)36-7/h14,18,20-23,33H,8-13,15-16H2,1-7H3/t18-,20-,21-,22-,23+,27-,28+,29-,30+,31+/m0/s1

> <INCHI_KEY>
MKDSBDQLSLPNOQ-ADTJVYGVSA-N

> <FORMULA>
C31H44O6

> <MOLECULAR_WEIGHT>
512.687

> <EXACT_MASS>
512.313789137

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
56.80739027152538

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1S,2R,5R,6R,9R,11S,14S,15R,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-5-carboxylate

> <ALOGPS_LOGP>
3.79

> <JCHEM_LOGP>
4.802574749

> <ALOGPS_LOGS>
-5.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.489419089743183

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.56895050008885

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351234668243886

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
138.7781

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.15e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1S,2R,5R,6R,9R,11S,14S,15R,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-5-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      15.978   0.292   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      14.438   0.322   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.695   1.670   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.152   2.169   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.457   3.192   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.155   1.701   0.000  0.00  0.00           C+0
HETATM    7  H   UNK     0      10.615   1.731   0.000  0.00  0.00           H+0
HETATM    8  C   UNK     0      11.411   3.049   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.872   3.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.076   1.761   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.819   0.413   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       8.279   0.443   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      11.359   0.382   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.563  -0.936   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.103  -0.966   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.642  -0.996   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.266   3.289   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.536   1.791   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.740   0.473   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.483  -0.876   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.023  -0.906   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.767  -2.254   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.332   3.110   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       7.588   4.458   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.384   5.776   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.595   3.990   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.792   3.140   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.252   3.170   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.456   1.852   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.938   2.111   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.789   1.086   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       3.816   3.252   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.200   0.503   0.000  0.00  0.00           C+0
HETATM   34  H   UNK     0       3.662   0.418   0.000  0.00  0.00           H+0
HETATM   35  C   UNK     0       4.609  -0.919   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.129  -1.344   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.870  -2.862   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.602   0.360   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       1.874  -0.452   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       0.526  -1.195   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7    8   13                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17   18                                             
CONECT   11   10   12   13   21                                             
CONECT   12   11                                                            
CONECT   13   11    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    2                                                       
CONECT   17   10                                                            
CONECT   18   10   19   23   27                                             
CONECT   19   18   20   33                                                  
CONECT   20   19   21                                                       
CONECT   21   20   11   22                                                  
CONECT   22   21                                                            
CONECT   23   18   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23                                                            
CONECT   27   18   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32   33                                             
CONECT   30   29   31   38                                                  
CONECT   31   30   39                                                       
CONECT   32   29                                                            
CONECT   33   29   19   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37   38   39                                             
CONECT   37   36                                                            
CONECT   38   36   30                                                       
CONECT   39   36   31   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   90    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1S,2R,5R,6R,9R,11S,14S,15R,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0,.0,.0,.0,]tetracos-17-ene-5-carboxylic acid	Generator

Chemical Formula

C₃₁H₄₄O₆

Average Mass

512.6870 Da

Monoisotopic Mass

512.31379 Da

IUPAC Name

methyl (1S,2R,5R,6R,9R,11S,14S,15R,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-5-carboxylate

Traditional Name

methyl (1S,2R,5R,6R,9R,11S,14S,15R,19S,21S)-11-hydroxy-2,6,10,10,14,21-hexamethyl-16,22-dioxo-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-5-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@]3(C)C[C@H](OC3=O)[C@]1(C)CC[C@]1(C(=O)OC)C2=CC(=O)[C@]2([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]12C

InChI Identifier

InChI=1S/C31H44O6/c1-26(2)20-8-11-30(6)23(29(20,5)10-9-21(26)33)19(32)14-17-18-15-27(3)16-22(37-24(27)34)28(18,4)12-13-31(17,30)25(35)36-7/h14,18,20-23,33H,8-13,15-16H2,1-7H3/t18-,20-,21-,22-,23+,27-,28+,29-,30+,31+/m0/s1

InChI Key

MKDSBDQLSLPNOQ-ADTJVYGVSA-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
Glycyrrhiza uralensis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
19-oxosteroid
Oxosteroid
Steroid
Caprolactone
Cyclohexenone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Cyclic alcohol
Methyl ester
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	3.79	ALOGPS
logP	4.8	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	16.57	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	138.78 m³·mol⁻¹	ChemAxon
Polarizability	56.81 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

C00056706

Chemspider ID

10277075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21669128

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Glyuranolide (NP0086435)

MOL for NP0086435 (Glyuranolide)

3D MOL for NP0086435 (Glyuranolide)

3D SDF for NP0086435 (Glyuranolide)

3D-SDF for NP0086435 (Glyuranolide)

PDB for NP0086435 (Glyuranolide)

3D PDB for NP0086435 (Glyuranolide)

SMILES for NP0086435 (Glyuranolide)

INCHI for NP0086435 (Glyuranolide)

Structure for NP0086435 (Glyuranolide)

3D Structure for NP0086435 (Glyuranolide)