NP-MRD: Showing NP-Card for Ganoderic acid U (NP0048386)

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Record Information

Version

2.0

Created at

2022-03-17 20:55:40 UTC

Updated at

2022-03-17 20:55:40 UTC

NP-MRD ID

NP0048386

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ganoderic acid U

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241211152D          

 34 37  0  0  0  0            999 V2000
   -2.5575   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139   -1.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698   -0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8538    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139    0.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    2.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842    1.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    1.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3426    0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883    0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289    1.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439    0.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -0.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042    1.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1499    1.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575   -0.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862   -0.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7012   -1.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8019   -2.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -2.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7012    0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 26  1  0  0  0  0
  1 32  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 24  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 34  1  0  0  0  0
 25 26  1  0  0  0  0
 26 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
 29 32  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END


  Mrv0541 02241211152D          

 34 37  0  0  0  0            999 V2000
   -2.5575   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139   -1.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698   -0.3513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8538    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3698    0.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139    0.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273    1.5490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0741    2.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.7676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4327    1.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842    1.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7913    1.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3426    0.8848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883    0.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289    1.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439    0.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8439   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1289   -0.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4139   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3273   -0.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042    1.8404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1499    1.0554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575    0.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5575   -0.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -0.0969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862   -0.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9862   -1.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7012   -1.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8019   -2.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2711   -1.7484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7418   -2.3795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7012    0.4421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 26  1  0  0  0  0
  1 32  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 20  1  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  8 17  1  0  0  0  0
  8 21  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 15 24  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 26  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 23 24  2  0  0  0  0
 24 34  1  0  0  0  0
 25 26  1  0  0  0  0
 26 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
 29 32  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048386

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC\C=C(/C)C(O)=O)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3O

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O4/c1-18(9-8-10-19(2)26(33)34)20-11-16-30(7)25-21(12-15-29(20,30)6)28(5)14-13-24(32)27(3,4)23(28)17-22(25)31/h10,18,20,22-24,31-32H,8-9,11-17H2,1-7H3,(H,33,34)/b19-10+

> <INCHI_KEY>
QHLHTTNIUVMWRY-VXLYETTFSA-N

> <FORMULA>
C30H48O4

> <MOLECULAR_WEIGHT>
472.6997

> <EXACT_MASS>
472.355260024

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
57.08885027549815

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-6-{5,9-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enoic acid

> <ALOGPS_LOGP>
5.76

> <JCHEM_LOGP>
5.667554053000002

> <ALOGPS_LOGS>
-5.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.55372930235658

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.812294621977863

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4770141605198971

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
137.77739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.00e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-6-{5,9-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enoic 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      -4.774  -2.491   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.442  -3.264   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.107  -2.491   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.773  -3.264   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.690  -0.656   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.594   0.589   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.690   1.836   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.773   1.359   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.611   2.891   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.138   4.442   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.168   3.300   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.674   3.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.704   2.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.210   2.796   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.240   1.652   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.765   0.186   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.107   2.129   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.442   1.359   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.442  -0.181   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.107  -0.951   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.773  -0.181   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.611  -1.713   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.221   3.435   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       7.746   1.970   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.774   0.589   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.774  -0.951   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.106  -0.181   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -7.441  -0.951   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -7.441  -2.491   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -8.776  -3.264   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -7.097  -4.442   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -6.106  -3.264   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.118  -4.442   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       8.776   0.825   0.000  0.00  0.00           O+0
CONECT    1    2   26   32                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3                                                            
CONECT    5    6   21                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9   17   21                                             
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11    7   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   24                                                  
CONECT   16   15                                                            
CONECT   17    8   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20    3   19   21                                                  
CONECT   21    5    8   20   22                                             
CONECT   22   21                                                            
CONECT   23   24                                                            
CONECT   24   15   23   34                                                  
CONECT   25   26                                                            
CONECT   26    1   19   25   27                                             
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   32                                                  
CONECT   30   29                                                            
CONECT   31   32                                                            
CONECT   32    1   29   31   33                                             
CONECT   33   32                                                            
CONECT   34   24                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Ganoderate u	Generator
(2E)-6-{5,9-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enoate	Generator

Chemical Formula

C₃₀H₄₈O₄

Average Mass

472.6997 Da

Monoisotopic Mass

472.35526 Da

IUPAC Name

(2E)-6-{5,9-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enoic acid

Traditional Name

(2E)-6-{5,9-dihydroxy-2,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methylhept-2-enoic acid

CAS Registry Number

86377-51-7

SMILES

CC(CC\C=C(/C)C(O)=O)C1CCC2(C)C3=C(CCC12C)C1(C)CCC(O)C(C)(C)C1CC3O

InChI Identifier

InChI=1S/C30H48O4/c1-18(9-8-10-19(2)26(33)34)20-11-16-30(7)25-21(12-15-29(20,30)6)28(5)14-13-24(32)27(3,4)23(28)17-22(25)31/h10,18,20,22-24,31-32H,8-9,11-17H2,1-7H3,(H,33,34)/b19-10+

InChI Key

QHLHTTNIUVMWRY-VXLYETTFSA-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

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	5.76	ALOGPS
logP	5.67	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	-0.48	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	137.78 m³·mol⁻¹	ChemAxon
Polarizability	57.09 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	No	ChemAxon

External Links

HMDB ID

HMDB0035962

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014766

KNApSAcK ID

C00023849

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

131751888

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Ganoderic acid U (NP0048386)

MOL for NP0048386 (Ganoderic acid U)

3D MOL for NP0048386 (Ganoderic acid U)

3D SDF for NP0048386 (Ganoderic acid U)

3D-SDF for NP0048386 (Ganoderic acid U)

PDB for NP0048386 (Ganoderic acid U)

3D PDB for NP0048386 (Ganoderic acid U)

SMILES for NP0048386 (Ganoderic acid U)

INCHI for NP0048386 (Ganoderic acid U)

Structure for NP0048386 (Ganoderic acid U)

3D Structure for NP0048386 (Ganoderic acid U)