NP-MRD: Showing NP-Card for 6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid (NP0190084)

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Record Information

Version

2.0

Created at

2022-09-04 06:41:48 UTC

Updated at

2022-09-04 06:41:48 UTC

NP-MRD ID

NP0190084

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid

Description

Ganoderic acid B, also known as ganoderate b, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Ganoderic acid B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, ganoderic acid b has been detected, but not quantified in, mushrooms. 6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid is found in Ganoderma sinense. This could make ganoderic acid b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308402D          

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M  END

     RDKit          3D

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M  END


  Mrv0541 05061308402D          

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   -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
   -5.8108    0.3149    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
 15  1  1  0  0  0  0
 15 10  1  0  0  0  0
 16  2  1  0  0  0  0
 16 11  1  0  0  0  0
 17 10  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 15  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 13  1  0  0  0  0
 22  8  1  0  0  0  0
 23 12  1  0  0  0  0
 24 20  1  0  0  0  0
 25 19  1  0  0  0  0
 25 24  2  0  0  0  0
 26 16  1  0  0  0  0
 27  3  1  0  0  0  0
 27  4  1  0  0  0  0
 27 21  1  0  0  0  0
 27 22  1  0  0  0  0
 28  5  1  0  0  0  0
 28  9  1  0  0  0  0
 28 21  1  0  0  0  0
 28 24  1  0  0  0  0
 29  6  1  0  0  0  0
 29 14  1  0  0  0  0
 29 18  1  0  0  0  0
 30  7  1  0  0  0  0
 30 23  1  0  0  0  0
 30 25  1  0  0  0  0
 30 29  1  0  0  0  0
 31 17  2  0  0  0  0
 32 19  1  0  0  0  0
 33 20  2  0  0  0  0
 34 22  1  0  0  0  0
 35 23  2  0  0  0  0
 36 26  2  0  0  0  0
 37 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190084

> <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)C1CC3O

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h15-16,18-19,21-22,32,34H,8-14H2,1-7H3,(H,36,37)

> <INCHI_KEY>
LWPLEHFGBRFRKI-UHFFFAOYSA-N

> <FORMULA>
C30H44O7

> <MOLECULAR_WEIGHT>
516.6662

> <EXACT_MASS>
516.308703762

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
55.9202632766731

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
3.303381904333333

> <ALOGPS_LOGS>
-4.62

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.51466313463079

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.314694886258931

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8070077635910818

> <JCHEM_POLAR_SURFACE_AREA>
128.96999999999997

> <JCHEM_REFRACTIVITY>
138.92929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{5,9-dihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[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     -14.257   6.766   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -12.750   6.446   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.681   3.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.014   3.395   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.510   1.863   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -12.829   2.373   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -8.231   5.486   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.015   4.165   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.320   4.165   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.348   4.165   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -6.349   3.395   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.323   2.052   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -9.738   5.806   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -13.305   3.837   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -15.287   5.622   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -8.016   1.543   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -10.768   4.661   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -10.292   3.197   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     -10.847   0.588   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0     -10.214   7.270   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0     -16.793   5.942   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -8.642   0.136   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0       2.987   4.165   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       1.653   1.855   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   27                                                            
CONECT    4   27                                                            
CONECT    5   28                                                            
CONECT    6   29                                                            
CONECT    7   30                                                            
CONECT    8    9   22                                                       
CONECT    9    8   28                                                       
CONECT   10   15   17                                                       
CONECT   11   16   17                                                       
CONECT   12   18   23                                                       
CONECT   13   19   21                                                       
CONECT   14   20   29                                                       
CONECT   15    1   10   18                                                  
CONECT   16    2   11   26                                                  
CONECT   17   10   11   31                                                  
CONECT   18   12   15   29                                                  
CONECT   19   13   25   32                                                  
CONECT   20   14   24   33                                                  
CONECT   21   13   27   28                                                  
CONECT   22    8   27   34                                                  
CONECT   23   12   30   35                                                  
CONECT   24   20   25   28                                                  
CONECT   25   19   24   30                                                  
CONECT   26   16   36   37                                                  
CONECT   27    3    4   21   22                                             
CONECT   28    5    9   21   24                                             
CONECT   29    6   14   18   30                                             
CONECT   30    7   23   25   29                                             
CONECT   31   17                                                            
CONECT   32   19                                                            
CONECT   33   20                                                            
CONECT   34   22                                                            
CONECT   35   23                                                            
CONECT   36   26                                                            
CONECT   37   26                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
Ganoderate b	Generator
6-{5,9-dihydroxy-2,6,6,11,15-pentamethyl-12,17-dioxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-14-yl}-2-methyl-4-oxoheptanoate	Generator
Ganoderic acid b	MeSH

Chemical Formula

C₃₀H₄₄O₇

Average Mass

516.6662 Da

Monoisotopic Mass

516.30870 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

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)C1CC3O

InChI Identifier

InChI=1S/C30H44O7/c1-15(10-17(31)11-16(2)26(36)37)18-12-23(35)30(7)25-19(32)13-21-27(3,4)22(34)8-9-28(21,5)24(25)20(33)14-29(18,30)6/h15-16,18-19,21-22,32,34H,8-14H2,1-7H3,(H,36,37)

InChI Key

LWPLEHFGBRFRKI-UHFFFAOYSA-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
Ganoderma sinense	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
Dihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
23-oxosteroid
Bile acid, alcohol, or derivatives
Steroid acid
Hydroxysteroid
3-hydroxysteroid
11-oxosteroid
15-oxosteroid
Oxosteroid
7-hydroxysteroid
Steroid
Medium-chain keto acid
Gamma-keto acid
Cyclohexenone
Keto acid
Cyclic alcohol
Secondary alcohol
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
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	3.72	ALOGPS
logP	3.3	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	4.31	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	128.97 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	138.93 m³·mol⁻¹	ChemAxon
Polarizability	55.92 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

HMDB0035719

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014443

KNApSAcK ID

C00023821

Chemspider ID

25993032

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14109389

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid (NP0190084)

MOL for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D MOL for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D SDF for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D-SDF for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

PDB for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D PDB for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

SMILES for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

INCHI for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

Structure for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)

3D Structure for NP0190084 (6-{4,7-dihydroxy-3a,6,6,9a,11a-pentamethyl-3,10-dioxo-1h,2h,4h,5h,5ah,7h,8h,9h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-4-oxoheptanoic acid)