NP-MRD: Showing NP-Card for Lucidenic acid F (NP0048507)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:57:33 UTC

Updated at

2022-03-17 20:57:33 UTC

NP-MRD ID

NP0048507

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Lucidenic acid F

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210372D          

 33 36  0  0  0  0            999 V2000
   -3.2494   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2494   -1.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5345   -2.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -1.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5345   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -2.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -1.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    0.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060    0.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005   -0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5813    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    0.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5331    1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9655    1.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    2.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567   -1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    1.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    0.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -2.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476   -2.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213   -2.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9655   -2.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    0.0254    0.0000 C   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  2  0  0  0  0
  3  4  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  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 33  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 29  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  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 27  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 26  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
 15 25  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END


  Mrv0541 02241210372D          

 33 36  0  0  0  0            999 V2000
   -3.2494   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2494   -1.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5345   -2.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -1.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5345   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -2.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -1.6246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925   -0.7982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -0.3863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    0.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3925    0.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1060    0.4359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005   -0.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5813    0.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    0.6880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1005    1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3842    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5331    1.5144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    1.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9655    1.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2494    2.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3567   -1.4249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196    1.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -1.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    0.8464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -2.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9476   -2.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1213   -2.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9655   -2.0379    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8208    0.0254    0.0000 C   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  2  0  0  0  0
  3  4  1  0  0  0  0
  3 30  1  0  0  0  0
  3 31  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 33  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 29  2  0  0  0  0
  9 10  2  0  0  0  0
  9 11  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 27  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 26  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
 15 25  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048507

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)=O)C1CC(=O)C2(C)C3=C(C(=O)CC12C)C1(C)CCC(=O)C(C)(C)C1CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O6/c1-14(7-8-21(32)33)15-11-20(31)27(6)23-16(28)12-18-24(2,3)19(30)9-10-25(18,4)22(23)17(29)13-26(15,27)5/h14-15,18H,7-13H2,1-6H3,(H,32,33)

> <INCHI_KEY>
GLUXWRYPXYKXKV-UHFFFAOYSA-N

> <FORMULA>
C27H36O6

> <MOLECULAR_WEIGHT>
456.5711

> <EXACT_MASS>
456.251188884

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
49.53125453692195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}pentanoic acid

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.177531432666668

> <ALOGPS_LOGS>
-4.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.917129120574227

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.18747717589689

> <JCHEM_PKA_STRONGEST_BASIC>
-7.097871150752913

> <JCHEM_POLAR_SURFACE_AREA>
105.57999999999998

> <JCHEM_REFRACTIVITY>
122.86679999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.71e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}pentanoic 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      -6.065  -1.490   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.065  -3.033   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.731  -3.804   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.399  -3.033   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.399  -1.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.731  -0.721   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.065  -3.804   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.733  -3.033   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.733  -1.490   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.065  -0.721   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.597  -0.721   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.597   0.814   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.733   1.580   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.065   0.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.054  -1.194   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.952   0.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.054   1.284   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.054   2.827   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.717   3.598   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.391   3.598   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.728   2.827   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.065   3.598   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.402   2.827   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.065   5.141   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.533  -2.660   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.597   2.356   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.597  -2.264   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -3.399   1.580   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.597  -3.804   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -5.502  -5.141   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.960  -5.141   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -7.402  -3.804   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -3.399   0.047   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   32                                                  
CONECT    3    2    4   30   31                                             
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   33                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   27                                             
CONECT   12   11   13   17   26                                             
CONECT   13   12   14                                                       
CONECT   14   10   13   28                                                  
CONECT   15   11   16   25                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16   18                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   15                                                            
CONECT   26   12                                                            
CONECT   27   11                                                            
CONECT   28   14                                                            
CONECT   29    8                                                            
CONECT   30    3                                                            
CONECT   31    3                                                            
CONECT   32    2                                                            
CONECT   33    5                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Lucidenate F	Generator
25,26,27-Trinor-3,7,11,15-tetraoxolanost-8-en-24-Oic acid	HMDB
4,4,14-Trimethyl-3,7,11,15-tetraoxochol-8-en-24-Oic acid	HMDB
4-{2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}pentanoate	Generator

Chemical Formula

C₂₇H₃₆O₆

Average Mass

456.5711 Da

Monoisotopic Mass

456.25119 Da

IUPAC Name

4-{2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}pentanoic acid

Traditional Name

4-{2,6,6,11,15-pentamethyl-5,9,12,17-tetraoxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}pentanoic acid

CAS Registry Number

98665-18-0

SMILES

CC(CCC(O)=O)C1CC(=O)C2(C)C3=C(C(=O)CC12C)C1(C)CCC(=O)C(C)(C)C1CC3=O

InChI Identifier

InChI=1S/C27H36O6/c1-14(7-8-21(32)33)15-11-20(31)27(6)23-16(28)12-18-24(2,3)19(30)9-10-25(18,4)22(23)17(29)13-26(15,27)5/h14-15,18H,7-13H2,1-6H3,(H,32,33)

InChI Key

GLUXWRYPXYKXKV-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
Ganoderma lucidum (FR.)KARST.	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

Not Available

Substituents

Not Available

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	3.64	ALOGPS
logP	4.18	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.19	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.58 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	122.87 m³·mol⁻¹	ChemAxon
Polarizability	49.53 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036436

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015323

KNApSAcK ID

C00024066

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

74028536

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Lucidenic acid F (NP0048507)

MOL for NP0048507 (Lucidenic acid F)

3D MOL for NP0048507 (Lucidenic acid F)

3D SDF for NP0048507 (Lucidenic acid F)

3D-SDF for NP0048507 (Lucidenic acid F)

PDB for NP0048507 (Lucidenic acid F)

3D PDB for NP0048507 (Lucidenic acid F)

SMILES for NP0048507 (Lucidenic acid F)

INCHI for NP0048507 (Lucidenic acid F)

Structure for NP0048507 (Lucidenic acid F)

3D Structure for NP0048507 (Lucidenic acid F)