NP-MRD: Showing NP-Card for Ganolucidic acid B (NP0048311)

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Record Information

Version

2.0

Created at

2022-03-17 20:54:27 UTC

Updated at

2022-03-17 20:54:27 UTC

NP-MRD ID

NP0048311

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ganolucidic acid B

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061308422D          

 36 39  0  0  0  0            999 V2000
   -2.6866    3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9634    1.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7516    2.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0236    3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5416    2.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1917    0.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0658    1.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8727    1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6375    3.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8306    3.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4097    2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5137    1.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2166    3.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1277    2.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1896    3.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2942    0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7687    2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9346    2.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5756    2.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    3.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4716    3.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9965    3.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298    0.0729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    0.9936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 16  1  1  0  0  0  0
 16 12  1  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  8  1  0  0  0  0
 20 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 15  1  0  0  0  0
 22  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 14  1  0  0  0  0
 25 19  2  0  0  0  0
 25 21  1  0  0  0  0
 26 17  1  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28  5  1  0  0  0  0
 28 11  1  0  0  0  0
 28 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29  6  1  0  0  0  0
 29 15  1  0  0  0  0
 29 20  1  0  0  0  0
 30  7  1  0  0  0  0
 30 19  1  0  0  0  0
 30 24  1  0  0  0  0
 30 29  1  0  0  0  0
 31 18  2  0  0  0  0
 32 21  2  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
 35 26  2  0  0  0  0
 36 26  1  0  0  0  0
M  END


  Mrv0541 05061308422D          

 36 39  0  0  0  0            999 V2000
   -2.6866    3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9634    1.4027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7516    2.1124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0236    3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5416    2.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1917    0.8736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0658    1.0995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8727    1.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6375    3.6249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8306    3.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9721    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4873    0.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4097    2.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6866    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1713    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5137    1.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4010    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2166    3.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1277    2.0556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1896    3.0118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2942    0.8266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7687    2.4972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    1.8186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9346    2.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5756    2.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547    2.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7067    1.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576    3.0561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4716    3.8949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9965    3.1833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6298    0.0729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6003    2.2311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8858    0.9936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 16  1  1  0  0  0  0
 16 12  1  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 18 12  1  0  0  0  0
 18 13  1  0  0  0  0
 19  8  1  0  0  0  0
 20 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 15  1  0  0  0  0
 22  9  1  0  0  0  0
 23 10  1  0  0  0  0
 24 14  1  0  0  0  0
 25 19  2  0  0  0  0
 25 21  1  0  0  0  0
 26 17  1  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 22  1  0  0  0  0
 27 23  1  0  0  0  0
 28  5  1  0  0  0  0
 28 11  1  0  0  0  0
 28 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29  6  1  0  0  0  0
 29 15  1  0  0  0  0
 29 20  1  0  0  0  0
 30  7  1  0  0  0  0
 30 19  1  0  0  0  0
 30 24  1  0  0  0  0
 30 29  1  0  0  0  0
 31 18  2  0  0  0  0
 32 21  2  0  0  0  0
 33 23  1  0  0  0  0
 34 24  1  0  0  0  0
 35 26  2  0  0  0  0
 36 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048311

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O6/c1-16(12-18(31)13-17(2)26(35)36)20-14-24(34)30(7)19-8-9-22-27(3,4)23(33)10-11-28(22,5)25(19)21(32)15-29(20,30)6/h16-17,20,22-24,33-34H,8-15H2,1-7H3,(H,35,36)

> <INCHI_KEY>
YPYHGMCHNBTMDB-UHFFFAOYSA-N

> <FORMULA>
C30H46O6

> <MOLECULAR_WEIGHT>
502.6826

> <EXACT_MASS>
502.329439204

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
57.12605703296067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.9706652656666668

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.55377231056278

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.3517701034894785

> <JCHEM_PKA_STRONGEST_BASIC>
-0.284133362984642

> <JCHEM_POLAR_SURFACE_AREA>
111.90000000000002

> <JCHEM_REFRACTIVITY>
138.23609999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.59e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{5,12-dihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-4-oxoheptanoic 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      -5.015   5.705   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.320   5.705   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -14.865   2.618   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -16.336   3.943   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -11.244   6.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.611   5.052   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -9.691   1.631   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -11.323   2.052   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.829   2.373   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -14.257   6.766   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -12.750   6.446   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.681   3.395   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.014   3.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.510   1.863   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.231   5.486   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.015   4.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.320   4.165   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.348   4.165   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -10.292   3.197   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -6.349   3.395   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.738   5.806   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -13.305   3.837   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -15.287   5.622   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.016   1.543   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.768   4.661   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.653   3.395   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0     -14.811   4.157   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -12.274   4.982   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.755   4.021   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.786   2.877   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.348   5.705   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0     -10.214   7.270   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -16.793   5.942   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -8.642   0.136   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0       2.987   4.165   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       1.653   1.855   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   27                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   19                                                       
CONECT    9    8   22                                                       
CONECT   10   11   23                                                       
CONECT   11   10   28                                                       
CONECT   12   16   18                                                       
CONECT   13   17   18                                                       
CONECT   14   20   24                                                       
CONECT   15   21   29                                                       
CONECT   16    1   12   20                                                  
CONECT   17    2   13   26                                                  
CONECT   18   12   13   31                                                  
CONECT   19    8   25   30                                                  
CONECT   20   14   16   29                                                  
CONECT   21   15   25   32                                                  
CONECT   22    9   27   28                                                  
CONECT   23   10   27   33                                                  
CONECT   24   14   30   34                                                  
CONECT   25   19   21   28                                                  
CONECT   26   17   35   36                                                  
CONECT   27    3    4   22   23                                             
CONECT   28    5   11   22   25                                             
CONECT   29    6   15   20   30                                             
CONECT   30    7   19   24   29                                             
CONECT   31   18                                                            
CONECT   32   21                                                            
CONECT   33   23                                                            
CONECT   34   24                                                            
CONECT   35   26                                                            
CONECT   36   26                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
Ganolucidate b	Generator
3,15-Dihydroxy-11,23-dioxolanost-8-en-26-Oic acid	HMDB
6-{5,12-dihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-4-oxoheptanoate	Generator

Chemical Formula

C₃₀H₄₆O₆

Average Mass

502.6826 Da

Monoisotopic Mass

502.32944 Da

IUPAC Name

6-{5,12-dihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-4-oxoheptanoic acid

Traditional Name

6-{5,12-dihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-4-oxoheptanoic acid

CAS Registry Number

98683-75-1

SMILES

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

InChI Identifier

InChI=1S/C30H46O6/c1-16(12-18(31)13-17(2)26(35)36)20-14-24(34)30(7)19-8-9-22-27(3,4)23(33)10-11-28(22,5)25(19)21(32)15-29(20,30)6/h16-17,20,22-24,33-34H,8-15H2,1-7H3,(H,35,36)

InChI Key

YPYHGMCHNBTMDB-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	4.14	ALOGPS
logP	3.97	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-0.28	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	138.24 m³·mol⁻¹	ChemAxon
Polarizability	57.13 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0035751

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014483

KNApSAcK ID

C00024063

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

73657197

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ganolucidic acid B (NP0048311)

MOL for NP0048311 (Ganolucidic acid B)

3D MOL for NP0048311 (Ganolucidic acid B)

3D SDF for NP0048311 (Ganolucidic acid B)

3D-SDF for NP0048311 (Ganolucidic acid B)

PDB for NP0048311 (Ganolucidic acid B)

3D PDB for NP0048311 (Ganolucidic acid B)

SMILES for NP0048311 (Ganolucidic acid B)

INCHI for NP0048311 (Ganolucidic acid B)

Structure for NP0048311 (Ganolucidic acid B)

3D Structure for NP0048311 (Ganolucidic acid B)