NP-MRD: Showing NP-Card for Lucidenic acid G (NP0048260)

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Record Information

Version

2.0

Created at

2022-03-17 20:53:39 UTC

Updated at

2022-03-17 20:53:39 UTC

NP-MRD ID

NP0048260

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lucidenic acid G

Description

Lucidenic acid G, also known as lucidenate g, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Lucidenic acid G is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, lucidenic acid g has been detected, but not quantified in, mushrooms. Lucidenic acid G is found in Ganoderma lucidum . This could make lucidenic acid g a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308352D          

 34 37  0  0  0  0            999 V2000
   -0.5528   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119    3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    2.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    2.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075    3.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -0.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1230    3.0489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -0.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    0.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14  1  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 19  8  1  0  0  0  0
 20 10  1  0  0  0  0
 21  7  1  0  0  0  0
 22 17  1  0  0  0  0
 23 16  1  0  0  0  0
 23 22  2  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 24 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25  3  1  0  0  0  0
 25 13  1  0  0  0  0
 25 18  1  0  0  0  0
 25 19  1  0  0  0  0
 26  4  1  0  0  0  0
 26 12  1  0  0  0  0
 26 15  1  0  0  0  0
 27  5  1  0  0  0  0
 27 20  1  0  0  0  0
 27 23  1  0  0  0  0
 27 26  1  0  0  0  0
 28 13  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  2  0  0  0  0
 31 19  2  0  0  0  0
 32 20  1  0  0  0  0
 33 21  2  0  0  0  0
 34 21  1  0  0  0  0
M  END


  Mrv0541 05061308352D          

 34 37  0  0  0  0            999 V2000
   -0.5528   -0.4466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6232    0.6018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7119    3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1073    0.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9451    2.5190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6810    0.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1873   -0.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2475    0.8922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4354    0.7470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5867    1.7614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6520    2.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9990    0.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7094    2.7131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637    0.3176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    0.9689    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399    2.6391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111    0.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1838    2.1537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5278    1.6682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0962    2.2244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0046   -0.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0914    1.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.8632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9035    1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960    2.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4672    0.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7475    1.7180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7075    3.5381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081    3.2699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3429   -0.1741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3399    1.8134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1230    3.0489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5109   -0.7594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3155    0.6561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14  1  1  0  0  0  0
 14  6  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18 11  1  0  0  0  0
 19  8  1  0  0  0  0
 20 10  1  0  0  0  0
 21  7  1  0  0  0  0
 22 17  1  0  0  0  0
 23 16  1  0  0  0  0
 23 22  2  0  0  0  0
 24  2  1  0  0  0  0
 24  9  1  0  0  0  0
 24 18  1  0  0  0  0
 24 22  1  0  0  0  0
 25  3  1  0  0  0  0
 25 13  1  0  0  0  0
 25 18  1  0  0  0  0
 25 19  1  0  0  0  0
 26  4  1  0  0  0  0
 26 12  1  0  0  0  0
 26 15  1  0  0  0  0
 27  5  1  0  0  0  0
 27 20  1  0  0  0  0
 27 23  1  0  0  0  0
 27 26  1  0  0  0  0
 28 13  1  0  0  0  0
 29 16  1  0  0  0  0
 30 17  2  0  0  0  0
 31 19  2  0  0  0  0
 32 20  1  0  0  0  0
 33 21  2  0  0  0  0
 34 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048260

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)=O)C1CC(O)C2(C)C3=C(C(=O)CC12C)C1(C)CCC(=O)C(C)(CO)C1CC3O

> <INCHI_IDENTIFIER>
InChI=1S/C27H40O7/c1-14(6-7-21(33)34)15-10-20(32)27(5)23-16(29)11-18-24(2,9-8-19(31)25(18,3)13-28)22(23)17(30)12-26(15,27)4/h14-16,18,20,28-29,32H,6-13H2,1-5H3,(H,33,34)

> <INCHI_KEY>
PWSMDKBWXADYJS-UHFFFAOYSA-N

> <FORMULA>
C27H40O7

> <MOLECULAR_WEIGHT>
476.6023

> <EXACT_MASS>
476.277403634

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
52.625267002439685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[9,12-dihydroxy-6-(hydroxymethyl)-2,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl]pentanoic acid

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
1.7697048646666662

> <ALOGPS_LOGS>
-3.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.185458293277748

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.302779116376273

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8187849249315393

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
126.28609999999993

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[9,12-dihydroxy-6-(hydroxymethyl)-2,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl]pentanoic 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      -1.032  -0.834   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.897   1.123   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.929   5.737   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.200   0.373   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.764   4.702   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.138   0.803   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.083  -0.412   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.929   1.665   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.413   1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.095   3.288   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.950   5.198   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.865   0.581   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.791   5.064   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.612   0.593   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.667   1.809   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.434   4.926   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.381   0.852   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.943   4.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.452   3.114   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.180   4.152   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.609  -0.202   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.904   2.301   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.911   3.478   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.420   2.572   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.459   4.291   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.872   1.759   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.395   3.207   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.787   6.604   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.442   6.104   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.373  -0.325   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       9.968   3.385   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.230   5.691   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -6.554  -1.418   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -6.189   1.225   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6    7   14                                                       
CONECT    7    6   21                                                       
CONECT    8    9   19                                                       
CONECT    9    8   24                                                       
CONECT   10   15   20                                                       
CONECT   11   16   18                                                       
CONECT   12   17   26                                                       
CONECT   13   25   28                                                       
CONECT   14    1    6   15                                                  
CONECT   15   10   14   26                                                  
CONECT   16   11   23   29                                                  
CONECT   17   12   22   30                                                  
CONECT   18   11   24   25                                                  
CONECT   19    8   25   31                                                  
CONECT   20   10   27   32                                                  
CONECT   21    7   33   34                                                  
CONECT   22   17   23   24                                                  
CONECT   23   16   22   27                                                  
CONECT   24    2    9   18   22                                             
CONECT   25    3   13   18   19                                             
CONECT   26    4   12   15   27                                             
CONECT   27    5   20   23   26                                             
CONECT   28   13                                                            
CONECT   29   16                                                            
CONECT   30   17                                                            
CONECT   31   19                                                            
CONECT   32   20                                                            
CONECT   33   21                                                            
CONECT   34   21                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Lucidenate g	Generator
3,11-Dioxo-4beta,7beta,15alpha-trihydroxy-5alpha-lanost-8-en-24-Oic acid	HMDB
7b,15a,29-Trihydroxy-3,11-dioxo-25,26,27-trinorlanost-8-en-24-Oic acid	HMDB
4-[9,12-Dihydroxy-6-(hydroxymethyl)-2,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl]pentanoate	Generator

Chemical Formula

C₂₇H₄₀O₇

Average Mass

476.6023 Da

Monoisotopic Mass

476.27740 Da

IUPAC Name

4-[9,12-dihydroxy-6-(hydroxymethyl)-2,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl]pentanoic acid

Traditional Name

4-[9,12-dihydroxy-6-(hydroxymethyl)-2,6,11,15-tetramethyl-5,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(O)=O)C1CC(O)C2(C)C3=C(C(=O)CC12C)C1(C)CCC(=O)C(C)(CO)C1CC3O

InChI Identifier

InChI=1S/C27H40O7/c1-14(6-7-21(33)34)15-10-20(32)27(5)23-16(29)11-18-24(2,9-8-19(31)25(18,3)13-28)22(23)17(30)12-26(15,27)4/h14-16,18,20,28-29,32H,6-13H2,1-5H3,(H,33,34)

InChI Key

PWSMDKBWXADYJS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Ganoderma lucidum	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
3-oxosteroid
6-hydroxysteroid
7-hydroxysteroid
15-hydroxysteroid
Hydroxysteroid
Oxosteroid
11-oxosteroid
Steroid
Cyclohexenone
Short-chain hydroxy acid
Cyclic alcohol
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
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	2.45	ALOGPS
logP	1.77	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	126.29 m³·mol⁻¹	ChemAxon
Polarizability	52.63 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035599

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014292

KNApSAcK ID

C00023879

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14109385

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lucidenic acid G (NP0048260)

MOL for NP0048260 (Lucidenic acid G)

3D MOL for NP0048260 (Lucidenic acid G)

3D SDF for NP0048260 (Lucidenic acid G)

3D-SDF for NP0048260 (Lucidenic acid G)

PDB for NP0048260 (Lucidenic acid G)

3D PDB for NP0048260 (Lucidenic acid G)

SMILES for NP0048260 (Lucidenic acid G)

INCHI for NP0048260 (Lucidenic acid G)

Structure for NP0048260 (Lucidenic acid G)

3D Structure for NP0048260 (Lucidenic acid G)