NP-MRD: Showing NP-Card for 18alpha-Glycyrrhetinic acid (NP0137530)

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Record Information

Version

2.0

Created at

2022-05-30 16:55:13 UTC

Updated at

2022-05-30 16:55:13 UTC

NP-MRD ID

NP0137530

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18alpha-Glycyrrhetinic acid

Description

Beta-Glycyrrhetinic acid, also known as b-glycyrrhetinate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Beta-Glycyrrhetinic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, beta-Glycyrrhetinic acid has been detected, but not quantified in, herbs and spices. 18alpha-Glycyrrhetinic acid is found in Glycyrrhiza glabra. This could make beta-glycyrrhetinic acid a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241219092D          

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M  END

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M  END


  Mrv0541 02241219092D          

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   -1.7384   -2.3350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7234    3.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5484    3.2190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734    3.2190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3349    4.0158    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
  1  6  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 13  1  0  0  0  0
  7 10  1  0  0  0  0
 12  7  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  2  0  0  0  0
 13 15  1  0  0  0  0
 14 13  1  0  0  0  0
 14 18  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 18 17  1  0  0  0  0
 20 18  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
 17 23  1  1  0  0  0
 18 24  1  6  0  0  0
 13 25  1  6  0  0  0
 10 26  1  1  0  0  0
 12 27  2  0  0  0  0
  7 28  1  6  0  0  0
  5 29  1  6  0  0  0
  6 30  1  1  0  0  0
  3 31  1  1  0  0  0
  4 32  1  0  0  0  0
  4 33  1  0  0  0  0
 19 34  1  6  0  0  0
 19 35  1  1  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137530

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21+,22+,23-,26-,27+,28+,29-,30-/m1/s1

> <INCHI_KEY>
MPDGHEJMBKOTSU-PMTKVOBESA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.6838

> <EXACT_MASS>
470.33960996

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
55.39138942197758

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-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

> <ALOGPS_LOGP>
5.45

> <JCHEM_LOGP>
6.031328036333333

> <ALOGPS_LOGS>
-5.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.48941909028516

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.444331881347185

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8351069321304386

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
134.2685

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.72e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.015   0.055   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.349  -0.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.349  -2.255   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.015  -3.025   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.681  -2.255   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.681  -0.715   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.348   0.055   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.348  -3.025   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.014  -2.255   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.014  -0.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.014   2.365   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.348   1.595   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.320   0.055   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.320   1.595   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.653  -0.715   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.987   0.055   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.987   1.595   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.653   2.365   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.987   4.675   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.653   3.905   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.321   2.365   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.321   3.905   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.987   3.135   0.000  0.00  0.00           C+0
HETATM   24  H   UNK     0       2.653   0.825   0.000  0.00  0.00           H+0
HETATM   25  C   UNK     0       1.320  -1.485   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.014   0.825   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.681   2.365   0.000  0.00  0.00           O+0
HETATM   28  H   UNK     0      -1.348  -1.485   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0      -2.681  -3.795   0.000  0.00  0.00           H+0
HETATM   30  C   UNK     0      -2.681   0.825   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.682  -3.025   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.104  -4.114   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.245  -4.359   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.217   6.009   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.757   6.009   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.297   6.009   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       4.358   7.496   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   32   33                                             
CONECT    5    4    6    8   29                                             
CONECT    6    1    7    5   30                                             
CONECT    7    6   10   12   28                                             
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   13    7   26                                             
CONECT   11   12   14                                                       
CONECT   12    7   11   27                                                  
CONECT   13   10   15   14   25                                             
CONECT   14   11   13   18                                                  
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   21   18   23                                             
CONECT   18   14   17   20   24                                             
CONECT   19   20   22   34   35                                             
CONECT   20   18   19                                                       
CONECT   21   17   22                                                       
CONECT   22   21   19                                                       
CONECT   23   17                                                            
CONECT   24   18                                                            
CONECT   25   13                                                            
CONECT   26   10                                                            
CONECT   27   12                                                            
CONECT   28    7                                                            
CONECT   29    5                                                            
CONECT   30    6                                                            
CONECT   31    3                                                            
CONECT   32    4                                                            
CONECT   33    4                                                            
CONECT   34   19                                                            
CONECT   35   19   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
b-Glycyrrhetinate	Generator
b-Glycyrrhetinic acid	Generator
beta-Glycyrrhetinate	Generator
Β-glycyrrhetinate	Generator
Β-glycyrrhetinic acid	Generator
18 alpha-Glycyrrhetinic acid	HMDB
18-Isoglycyrrhetinic acid	HMDB
18a-Glycyrrhetic acid	HMDB
18alpha-Olean-12-en-30-Oic acid, 3beta-hydroxy-11-oxo- (6ci,7ci,8ci)	HMDB
3-Hydroxy-11-oxo-(3beta,18alpha,20beta)-olean-12-en-29-Oic acid	HMDB
Isoglycyrrhetinic acid	HMDB
18a-Glycyrrhetinate	Generator
18a-Glycyrrhetinic acid	Generator
18alpha-Glycyrrhetinate	Generator
18Α-glycyrrhetinate	Generator
18Α-glycyrrhetinic acid	Generator
18beta-Glycyrrhetinic acid	MeSH
18alpha-GA	MeSH
18beta-GA	MeSH

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6838 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-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 Name

(2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,7,8,8a,10,11,12,12b,14b-dodecahydro-1H-picene-2-carboxylic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21+,22+,23-,26-,27+,28+,29-,30-/m1/s1

InChI Key

MPDGHEJMBKOTSU-PMTKVOBESA-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
Glycyrrhiza glabra	LOTUS Database	35616633

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
Cyclohexenone
Cyclic alcohol
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	5.45	ALOGPS
logP	6.03	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	4.44	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	134.27 m³·mol⁻¹	ChemAxon
Polarizability	55.39 Å³	ChemAxon
Number of Rings	5	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

HMDB0034517

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013018

KNApSAcK ID

Not Available

Chemspider ID

66115

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73398

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 18alpha-Glycyrrhetinic acid (NP0137530)

MOL for NP0137530 (18alpha-Glycyrrhetinic acid)

3D MOL for NP0137530 (18alpha-Glycyrrhetinic acid)

3D SDF for NP0137530 (18alpha-Glycyrrhetinic acid)

3D-SDF for NP0137530 (18alpha-Glycyrrhetinic acid)

PDB for NP0137530 (18alpha-Glycyrrhetinic acid)

3D PDB for NP0137530 (18alpha-Glycyrrhetinic acid)

SMILES for NP0137530 (18alpha-Glycyrrhetinic acid)

INCHI for NP0137530 (18alpha-Glycyrrhetinic acid)

Structure for NP0137530 (18alpha-Glycyrrhetinic acid)

3D Structure for NP0137530 (18alpha-Glycyrrhetinic acid)