NP-MRD: Showing NP-Card for 6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid (NP0193595)

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Record Information

Version

2.0

Created at

2022-09-04 11:05:08 UTC

Updated at

2022-09-04 11:05:09 UTC

NP-MRD ID

NP0193595

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid

Description

Ganoderic acid S, also known as ganoderate S, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid was first documented in 2005 (PMID: 15938193). Based on a literature review a significant number of articles have been published on ganoderic acid S (PMID: 17050181) (PMID: 30317980) (PMID: 29748985) (PMID: 28078535) (PMID: 26292672) (PMID: 21036023).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042213052D          

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 14 15  1  0  0  0  0
 16 15  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 13 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
  8 29  1  0  0  0  0
 11 29  1  0  0  0  0
 29 30  1  1  0  0  0
  2 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193595

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C(O)=O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h10-11,14,19,21,24H,8-9,12-13,15-18H2,1-7H3,(H,32,33)/t19?,21-,24+,28-,29-,30+/m1/s1

> <INCHI_KEY>
AQUHIKXTCOSRFY-QREPNUMGSA-N

> <FORMULA>
C30H44O3

> <MOLECULAR_WEIGHT>
452.679

> <EXACT_MASS>
452.329045277

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.834087562598086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-6-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]hept-2-enoic acid

> <JCHEM_LOGP>
7.099971169000001

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.635198846136838

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.852452401143215

> <JCHEM_PKA_STRONGEST_BASIC>
-7.47149360495432

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
136.55620000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-6-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]hept-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       2.527 -10.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.053 -11.147   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.998  -9.932   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.417  -8.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.363  -7.289   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.257  -5.652   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.159  -1.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.323  -0.719   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.185  -1.391   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.633 -12.574   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.158 -12.785   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       3.688 -13.790   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   29                                             
CONECT   12   11                                                            
CONECT   13   11   14   26                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   16   25   26                                             
CONECT   25   24                                                            
CONECT   26   24   13   27                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28    8   11   30                                             
CONECT   30   29                                                            
CONECT   31    2   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
Ganoderate S	Generator
Ganoderic acid SZ	MeSH

Chemical Formula

C₃₀H₄₄O₃

Average Mass

452.6790 Da

Monoisotopic Mass

452.32905 Da

IUPAC Name

2-methyl-6-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]hept-2-enoic acid

Traditional Name

2-methyl-6-[(2S,7R,11R,14R,15R)-2,6,6,11,15-pentamethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(17),9-dien-14-yl]hept-2-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C(O)=O)[C@H]1CC[C@@]2(C)C3=CC[C@H]4C(C)(C)C(=O)CC[C@]4(C)C3=CC[C@]12C

InChI Identifier

InChI=1S/C30H44O3/c1-19(9-8-10-20(2)26(32)33)21-13-17-30(7)23-11-12-24-27(3,4)25(31)15-16-28(24,5)22(23)14-18-29(21,30)6/h10-11,14,19,21,24H,8-9,12-13,15-18H2,1-7H3,(H,32,33)/t19?,21-,24+,28-,29-,30+/m1/s1

InChI Key

AQUHIKXTCOSRFY-QREPNUMGSA-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

Not Available

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
Cholane-skeleton
Bile acid, alcohol, or derivatives
Steroid acid
14-alpha-methylsteroid
3-oxo-5-alpha-steroid
Oxosteroid
3-oxosteroid
3-oxo-delta-7-steroid
Steroid
Delta-7-steroid
Medium-chain fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	7.1	ChemAxon
pKa (Strongest Acidic)	4.85	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.56 m³·mol⁻¹	ChemAxon
Polarizability	54.83 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023847

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

129317011

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Li C, Li Y, Sun HH: New ganoderic acids, bioactive triterpenoid metabolites from the mushroom Ganoderma lucidum. Nat Prod Res. 2006 Sep;20(11):985-91. doi: 10.1080/14786410600921466. [PubMed:17050181 ]
Li C, Yin J, Guo F, Zhang D, Sun HH: Ganoderic acid Sz, a new lanostanoid from the mushroom Ganoderma lucidum. Nat Prod Res. 2005 Jul;19(5):461-5. doi: 10.1080/14786410412331272077. [PubMed:15938193 ]
Zhou S, Tang Q, Tang C, Liu Y, Ma F, Zhang X, Zhang JS: Triterpenes and Soluble Polysaccharide Changes in Lingzhi or Reishi Medicinal Mushroom, Ganoderma lucidum (Agaricomycetes), During Fruiting Growth. Int J Med Mushrooms. 2018;20(9):859-871. doi: 10.1615/IntJMedMushrooms.2018027357. [PubMed:30317980 ]
Feng N, Wei Y, Feng J, Tang Q, Zhang Z, Zhang J, Han W: Preparative isolation of ganoderic acid S, ganoderic acid T and ganoderol B from Ganoderma lucidum mycelia by high-speed counter-current chromatography. Biomed Chromatogr. 2018 Oct;32(10):e4283. doi: 10.1002/bmc.4283. Epub 2018 May 31. [PubMed:29748985 ]
Kohno T, Hai-Bang T, Zhu Q, Amen Y, Sakamoto S, Tanaka H, Morimoto S, Shimizu K: Tubulin polymerization-stimulating activity of Ganoderma triterpenoids. J Nat Med. 2017 Apr;71(2):457-462. doi: 10.1007/s11418-017-1072-y. Epub 2017 Jan 11. [PubMed:28078535 ]
Ruan W, Wei Y, Popovich DG: Distinct Responses of Cytotoxic Ganoderma lucidum Triterpenoids in Human Carcinoma Cells. Phytother Res. 2015 Nov;29(11):1744-52. doi: 10.1002/ptr.5426. Epub 2015 Aug 21. [PubMed:26292672 ]
Liu RM, Zhong JJ: Ganoderic acid Mf and S induce mitochondria mediated apoptosis in human cervical carcinoma HeLa cells. Phytomedicine. 2011 Mar 15;18(5):349-55. doi: 10.1016/j.phymed.2010.08.019. Epub 2010 Oct 29. [PubMed:21036023 ]
Ding N, Yang Q, Huang SS, Fan LY, Zhang W, Zhong JJ, Cao CX: Separation and determination of four ganoderic acids from dried fermentation mycelia powder of Ganoderma lucidum by capillary zone electrophoresis. J Pharm Biomed Anal. 2010 Dec 15;53(5):1224-30. doi: 10.1016/j.jpba.2010.07.025. Epub 2010 Aug 16. [PubMed:20719456 ]
LOTUS database [Link]

Showing NP-Card for 6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid (NP0193595)

MOL for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D MOL for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D SDF for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D-SDF for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

PDB for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D PDB for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

SMILES for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

INCHI for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

Structure for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)

3D Structure for NP0193595 (6-[(1r,3ar,5ar,9as,11ar)-3a,6,6,9a,11a-pentamethyl-7-oxo-1h,2h,3h,5h,5ah,8h,9h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-2-enoic acid)