NP-MRD: Showing NP-Card for 3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid (NP0309250)

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Record Information

Version

2.0

Created at

2022-09-11 03:43:22 UTC

Updated at

2022-09-11 03:43:22 UTC

NP-MRD ID

NP0309250

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid

Description

Ganoboninone A belongs to the class of organic compounds known as carbocyclic fatty acids. These are fatty acids containing a carbocyclic ring. 3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid is found in Ganoderma boninense. Based on a literature review very few articles have been published on Ganoboninone A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112205432D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112205432D          

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    2.5823   -1.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -1.7385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4940   -0.9567    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  7  6  1  6  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 22 25  1  1  0  0  0
 21 26  1  0  0  0  0
 16 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 17 33  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  6  0  0  0
  7 37  1  0  0  0  0
 11 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309250

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)CC[C@]1(C)OC[C@@]23[C@@H]1CC[C@@]2(C)C1=C(C(=O)C3=O)[C@@](C)(CCC(O)=O)[C@@H](CC1=O)[C@@]1(C)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O8/c1-6-16(30)7-12-27(4)18-8-11-26(3)21-17(31)13-19(28(5)14-36-28)25(2,10-9-20(32)33)22(21)23(34)24(35)29(18,26)15-37-27/h18-19H,6-15H2,1-5H3,(H,32,33)/t18-,19-,25+,26+,27+,28-,29+/m1/s1

> <INCHI_KEY>
ASUPBUQSWCPYPH-HDXHAILPSA-N

> <FORMULA>
C29H38O8

> <MOLECULAR_WEIGHT>
514.615

> <EXACT_MASS>
514.256668184

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.03650387627103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1R,5S,6R,10S,13S,14S)-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoic acid

> <JCHEM_LOGP>
3.4742084156666646

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.718916168719204

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.152863924005439

> <JCHEM_PKA_STRONGEST_BASIC>
-3.88693089197155

> <JCHEM_POLAR_SURFACE_AREA>
127.33999999999999

> <JCHEM_REFRACTIVITY>
133.78809999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1R,5S,6R,10S,13S,14S)-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -5.180  -0.898   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.766  -1.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.530  -0.590   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -2.707   0.939   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.116  -1.202   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.120  -0.283   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.533  -0.894   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.778  -2.236   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.993   0.576   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.533   0.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.025  -0.867   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.169   0.666   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.914   1.558   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.569   1.307   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.714   2.841   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.825   0.416   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.680  -1.117   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.936  -2.009   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.792  -3.542   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.336  -1.368   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.480   0.166   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.880   0.807   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.755  -0.460   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.492   2.297   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.977   1.889   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.225   1.057   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.072   2.343   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.633   2.479   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.568   3.703   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.975   5.124   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.448   5.322   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       8.910   6.348   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.280  -1.759   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.436  -2.777   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.820  -3.229   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.280  -3.245   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.789  -1.786   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   37                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   33   37                                             
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   26                                                  
CONECT   17   16   18   33                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   22                                                       
CONECT   26   21   16   27   28                                             
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   17   11   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₈O₈

Average Mass

514.6150 Da

Monoisotopic Mass

514.25667 Da

IUPAC Name

3-[(1R,5S,6R,10S,13S,14S)-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoic acid

Traditional Name

3-[(1R,5S,6R,10S,13S,14S)-5,10,14-trimethyl-6-[(2S)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0^{1,13}.0^{4,9}]hexadec-4(9)-en-5-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

CCC(=O)CC[C@]1(C)OC[C@@]23[C@@H]1CC[C@@]2(C)C1=C(C(=O)C3=O)[C@@](C)(CCC(O)=O)[C@@H](CC1=O)[C@@]1(C)CO1

InChI Identifier

InChI=1S/C29H38O8/c1-6-16(30)7-12-27(4)18-8-11-26(3)21-17(31)13-19(28(5)14-36-28)25(2,10-9-20(32)33)22(21)23(34)24(35)29(18,26)15-37-27/h18-19H,6-15H2,1-5H3,(H,32,33)/t18-,19-,25+,26+,27+,28-,29+/m1/s1

InChI Key

ASUPBUQSWCPYPH-HDXHAILPSA-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 boninense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbocyclic fatty acids. These are fatty acids containing a carbocyclic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Carbocyclic fatty acids

Alternative Parents

Substituents

Carbocyclic fatty acid
Cyclohexenone
Tetrahydrofuran
Ketone
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	3.47	ChemAxon
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	127.34 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	133.79 m³·mol⁻¹	ChemAxon
Polarizability	55.04 Å³	ChemAxon
Number of Rings	5	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78438198

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

122370814

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid (NP0309250)

MOL for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

3D MOL for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

3D SDF for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

3D-SDF for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

PDB for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

3D PDB for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

SMILES for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

INCHI for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

Structure for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)

3D Structure for NP0309250 (3-[(1r,5s,6r,10s,13s,14s)-5,10,14-trimethyl-6-[(2s)-2-methyloxiran-2-yl]-2,3,8-trioxo-14-(3-oxopentyl)-15-oxatetracyclo[8.6.0.0¹,¹³.0⁴,⁹]hexadec-4(9)-en-5-yl]propanoic acid)