NP-MRD: Showing NP-Card for (5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid (NP0180707)

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Record Information

Version

2.0

Created at

2022-09-03 19:06:45 UTC

Updated at

2022-09-03 19:06:45 UTC

NP-MRD ID

NP0180707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid

Description

Applanoxidic acid F, also known as applanoxidate F, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid is found in Ganoderma applanatum. Based on a literature review very few articles have been published on Applanoxidic acid F.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032221062D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309032221062D          

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    5.2898   -2.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4777   -1.9412    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6656   -1.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1974   -1.1653    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 12  2  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 30 33  1  0  0  0  0
 24 33  1  0  0  0  0
 33 34  1  6  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 37 36  1  1  0  0  0
 23 37  1  0  0  0  0
 35 37  1  0  0  0  0
 16 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0180707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(=O)\C=C(/C)[C@H]1CC(=O)[C@@]2(C)[C@@]34O[C@@H]3C[C@H]3C(C)(C)C(=O)CC[C@]3(C)C4=CC(=O)[C@]12C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O7/c1-15(10-17(31)11-16(2)25(35)36)18-12-23(34)29(7)28(18,6)22(33)13-20-27(5)9-8-21(32)26(3,4)19(27)14-24-30(20,29)37-24/h10,13,16,18-19,24H,8-9,11-12,14H2,1-7H3,(H,35,36)/b15-10+/t16?,18-,19+,24-,27+,28+,29-,30+/m1/s1

> <INCHI_KEY>
IFIKIFMCHAMBFO-LOKDDDFESA-N

> <FORMULA>
C30H38O7

> <MOLECULAR_WEIGHT>
510.627

> <EXACT_MASS>
510.261753564

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
54.75128422518848

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5E)-2-methyl-4-oxo-6-[(1R,3R,5R,10S,14R,15R,18R)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0^{1,3}.0^{5,10}.0^{14,18}]octadec-11-en-15-yl]hept-5-enoic acid

> <JCHEM_LOGP>
4.538696973333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.58393378388808

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.059009204164726

> <JCHEM_PKA_STRONGEST_BASIC>
-4.143634497344335

> <JCHEM_POLAR_SURFACE_AREA>
118.10999999999999

> <JCHEM_REFRACTIVITY>
136.88699999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5E)-2-methyl-4-oxo-6-[(1R,3R,5R,10S,14R,15R,18R)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0^{1,3}.0^{5,10}.0^{14,18}]octadec-11-en-15-yl]hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       3.892   2.137   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.312   0.710   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.786   0.499   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.841   1.715   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.685   1.505   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.421   3.142   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.476   4.357   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.049   4.147   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.056   5.784   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.111   7.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.582   5.995   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.257  -0.506   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.829  -1.985   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.103  -2.849   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.153  -4.388   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.319  -1.904   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.208  -3.440   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.796  -0.456   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.124   0.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.789   0.722   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.266   2.170   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.305   0.451   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.828  -0.998   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      10.344  -1.269   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.821   0.179   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.337  -0.092   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.853  -0.363   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.376  -1.811   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.892  -2.082   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.383  -2.988   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      13.715  -3.762   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.853  -4.434   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.867  -2.717   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.874  -3.895   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       8.358  -3.624   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.842  -3.353   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       7.835  -2.175   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    2   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   37                                             
CONECT   17   16                                                            
CONECT   18   16   12   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   37                                                  
CONECT   24   23   25   26   33                                             
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   33                                             
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   30   24   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35   37                                                       
CONECT   37   36   23   35   16                                             
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
Applanoxidate F	Generator

Chemical Formula

C₃₀H₃₈O₇

Average Mass

510.6270 Da

Monoisotopic Mass

510.26175 Da

IUPAC Name

(5E)-2-methyl-4-oxo-6-[(1R,3R,5R,10S,14R,15R,18R)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0^{1,3}.0^{5,10}.0^{14,18}]octadec-11-en-15-yl]hept-5-enoic acid

Traditional Name

(5E)-2-methyl-4-oxo-6-[(1R,3R,5R,10S,14R,15R,18R)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0^{1,3}.0^{5,10}.0^{14,18}]octadec-11-en-15-yl]hept-5-enoic acid

CAS Registry Number

Not Available

SMILES

CC(CC(=O)\C=C(/C)[C@H]1CC(=O)[C@@]2(C)[C@@]34O[C@@H]3C[C@H]3C(C)(C)C(=O)CC[C@]3(C)C4=CC(=O)[C@]12C)C(O)=O

InChI Identifier

InChI=1S/C30H38O7/c1-15(10-17(31)11-16(2)25(35)36)18-12-23(34)29(7)28(18,6)22(33)13-20-27(5)9-8-21(32)26(3,4)19(27)14-24-30(20,29)37-24/h10,13,16,18-19,24H,8-9,11-12,14H2,1-7H3,(H,35,36)/b15-10+/t16?,18-,19+,24-,27+,28+,29-,30+/m1/s1

InChI Key

IFIKIFMCHAMBFO-LOKDDDFESA-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 applanatum	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
Cholane-skeleton
Medium-chain keto acid
Gamma-keto acid
Branched fatty acid
Cyclohexenone
Heterocyclic fatty acid
Oxepane
Methyl-branched fatty acid
Keto acid
Fatty acyl
Unsaturated fatty acid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
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	4.54	ChemAxon
pKa (Strongest Acidic)	4.06	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	118.11 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	136.89 m³·mol⁻¹	ChemAxon
Polarizability	54.75 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00035047

Chemspider ID

8159412

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9983822

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid (NP0180707)

MOL for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

3D MOL for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

3D SDF for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

3D-SDF for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

PDB for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

3D PDB for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

SMILES for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

INCHI for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

Structure for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)

3D Structure for NP0180707 ((5e)-2-methyl-4-oxo-6-[(1r,3r,5r,10s,14r,15r,18r)-6,6,10,14,18-pentamethyl-7,13,17-trioxo-2-oxapentacyclo[9.7.0.0¹,³.0⁵,¹⁰.0¹⁴,¹⁸]octadec-11-en-15-yl]hept-5-enoic acid)