NP-MRD: Showing NP-Card for 2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid (NP0314439)

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Record Information

Version

2.0

Created at

2022-09-11 12:32:07 UTC

Updated at

2022-09-11 12:32:08 UTC

NP-MRD ID

NP0314439

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid

Description

2-Methyl-4-oxo-6-{5,9,12-trihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl}heptanoic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review very few articles have been published on 2-methyl-4-oxo-6-{5,9,12-trihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadecan-14-yl}heptanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112214322D          

 37 40  0  0  0  0            999 V2000
    7.6879   -0.9936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2223   -3.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  9 10  1  0  0  0  0
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  9 33  1  0  0  0  0
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 33 34  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309112214322D          

 37 40  0  0  0  0            999 V2000
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   -0.6730   -1.0379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4800   -0.8664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1210   -0.4248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6860   -0.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9409   -1.3810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4930   -0.7679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7479   -1.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2999   -0.9394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0450   -0.1548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1069   -1.1109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3618   -1.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9749   -1.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -2.2311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1168   -1.8186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4023   -3.0561    0.0000 O   0  0  0  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  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 20 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 19 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 15 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
 32 33  1  0  0  0  0
  9 33  1  0  0  0  0
 13 33  1  0  0  0  0
 33 34  1  0  0  0  0
  2 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0314439

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC(=O)CC(C)C(O)=O)C1CC(O)C2(C)C3C(O)CC4C(C)(C)C(O)CCC4(C)C3C(=O)CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H48O7/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/h15-16,18-19,21-25,32,34-35H,8-14H2,1-7H3,(H,36,37)

> <INCHI_KEY>
RQIBZQHGLWMLEC-UHFFFAOYSA-N

> <FORMULA>
C30H48O7

> <MOLECULAR_WEIGHT>
520.707

> <EXACT_MASS>
520.340003886

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
85

> <JCHEM_AVERAGE_POLARIZABILITY>
58.20625300429232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-methyl-4-oxo-6-{5,9,12-trihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}heptanoic acid

> <JCHEM_LOGP>
2.8551705926666653

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.465453337642849

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.316877978775804

> <JCHEM_PKA_STRONGEST_BASIC>
-0.835155803613801

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
139.2193

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-4-oxo-6-{5,9,12-trihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}heptanoic 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      14.351  -1.855   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.351  -3.395   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.017  -4.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.683  -3.395   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      11.683  -1.855   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      10.350  -4.165   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.016  -3.395   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.016  -1.855   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.682  -4.165   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.521  -5.696   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.015  -6.016   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.389  -7.423   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.245  -4.683   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.340  -5.929   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.739  -4.363   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.708  -5.507   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.184  -6.972   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.202  -5.187   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.726  -3.722   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.780  -3.402   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.834  -4.941   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.305  -3.616   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.256  -1.937   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.763  -1.617   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.226  -0.793   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.281  -1.113   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.756  -2.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.787  -1.433   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.263  -2.898   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.293  -1.754   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.817  -0.289   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       5.800  -2.074   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.275  -3.538   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.420  -2.508   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      15.684  -4.165   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      17.018  -3.395   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      15.684  -5.705   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
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   33                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   33                                             
CONECT   14   13                                                            
CONECT   15   13   16   29                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   27                                                  
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   19   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   15   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32    9   13   34                                             
CONECT   34   33                                                            
CONECT   35    2   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Value	Source
2-Methyl-4-oxo-6-{5,9,12-trihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0,.0,]heptadecan-14-yl}heptanoate	Generator

Chemical Formula

C₃₀H₄₈O₇

Average Mass

520.7070 Da

Monoisotopic Mass

520.34000 Da

IUPAC Name

2-methyl-4-oxo-6-{5,9,12-trihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}heptanoic acid

Traditional Name

2-methyl-4-oxo-6-{5,9,12-trihydroxy-2,6,6,11,15-pentamethyl-17-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl}heptanoic acid

CAS Registry Number

Not Available

SMILES

CC(CC(=O)CC(C)C(O)=O)C1CC(O)C2(C)C3C(O)CC4C(C)(C)C(O)CCC4(C)C3C(=O)CC12C

InChI Identifier

InChI=1S/C30H48O7/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/h15-16,18-19,21-25,32,34-35H,8-14H2,1-7H3,(H,36,37)

InChI Key

RQIBZQHGLWMLEC-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

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
Trihydroxy bile acid, alcohol, or derivatives
Cholane-skeleton
23-oxosteroid
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
Steroid acid
7-hydroxysteroid
Oxosteroid
11-oxosteroid
Hydroxysteroid
15-hydroxysteroid
3-hydroxysteroid
Steroid
Medium-chain keto acid
Gamma-keto acid
Keto acid
Cyclic alcohol
Secondary alcohol
Ketone
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	2.86	ChemAxon
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	-0.84	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	139.22 m³·mol⁻¹	ChemAxon
Polarizability	58.21 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4476355

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317500

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid (NP0314439)

MOL for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

3D MOL for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

3D SDF for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

3D-SDF for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

PDB for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

3D PDB for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

SMILES for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

INCHI for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

Structure for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)

3D Structure for NP0314439 (2-methyl-4-oxo-6-{3,4,7-trihydroxy-3a,6,6,9a,11a-pentamethyl-10-oxo-dodecahydrocyclopenta[a]phenanthren-1-yl}heptanoic acid)