NP-MRD: Showing NP-Card for 3-Methyl-5-pentyl-2-furannonanoic acid (NP0336593)

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Record Information

Version

2.0

Created at

2024-09-11 07:00:15 UTC

Updated at

2024-09-11 07:00:15 UTC

NP-MRD ID

NP0336593

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Methyl-5-pentyl-2-furannonanoic acid

Description

3-Methyl-5-pentyl-2-furannonanoic acid, also known as emod F-acid or F2 acid, belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid. It is a component of F acid fraction present in beef blood serum. 3-Methyl-5-pentyl-2-furannonanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Methyl-5-pentyl-2-furannonanoic acid, in particular, can be described by the shorthand notation 9M5. They are often incorporated into phospholipids and cholesterol esters of fish and other marine organisms. Despite being found in low concentrations in food lipids, they are excellent antixoxidants and radical scavengers. F-acids are heterocyclic fatty acids containing a central furan moiety with a carboxylalkyl chain (mostly 7, 9, 11, or 13 carbons) in the 2-position and an alkyl chain (mostly 3 or 5 carbons) in the 5-position. This allows them to play an important role in preventing lipid peroxidation and protecting polyunsaturated fatty acids. This refers to its 9-carbon carboxyalkyl moiety, the methyl substitution in the 3-position of its furan moiety, and its 5-carbon alkyl moiety. 3-Methyl-5-pentyl-2-furannonanoic acid is a furan fatty acid (F-acid).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061305432D          

 22 22  0  0  0  0            999 V2000
   17.0156   -0.5676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4000    4.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6801    0.1861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8596    0.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6169    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9024    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3314    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1880    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5240    1.0260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0458    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4735    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7035    1.1122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7603    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7590    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7805    2.5803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2285    3.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3680    1.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4748    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0445    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3301    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0445    4.0954    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5610    2.0374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  4  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  1  0  0  0  0
 16  2  1  0  0  0  0
 16 15  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 18 13  1  0  0  0  0
 18 16  2  0  0  0  0
 19 14  1  0  0  0  0
 20 19  2  0  0  0  0
 21 19  1  0  0  0  0
 22 17  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336593

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC(C)=C(CCCCCCCCC(O)=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C19H32O3/c1-3-4-9-12-17-15-16(2)18(22-17)13-10-7-5-6-8-11-14-19(20)21/h15H,3-14H2,1-2H3,(H,20,21)

> <INCHI_KEY>
TUQVXFOSXOCQCM-UHFFFAOYSA-N

> <FORMULA>
C19H32O3

> <MOLECULAR_WEIGHT>
308.4556

> <EXACT_MASS>
308.23514489

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
39.13492083179564

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-(3-methyl-5-pentylfuran-2-yl)nonanoic acid

> <ALOGPS_LOGP>
6.21

> <JCHEM_LOGP>
6.196525046666666

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.869512823460774

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6878636215899308

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
90.6354

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.66e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(3-methyl-5-pentylfuran-2-yl)nonanoic 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      31.762  -1.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      26.880   7.467   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.136   0.347   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.605   0.508   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.818   5.335   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.484   6.105   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.152   6.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.151   5.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.978   1.915   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      22.485   5.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.817   6.105   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.447   2.076   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.819   6.105   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.483   5.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.590   4.817   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.560   5.961   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.820   3.483   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.153   5.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.150   6.105   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      11.816   5.335   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      13.150   7.645   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      25.314   3.803   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   16                                                            
CONECT    3    1    4                                                       
CONECT    4    3    9                                                       
CONECT    5    6    7                                                       
CONECT    6    5    8                                                       
CONECT    7    5   10                                                       
CONECT    8    6   11                                                       
CONECT    9    4   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   14                                                       
CONECT   12    9   17                                                       
CONECT   13   10   18                                                       
CONECT   14   11   19                                                       
CONECT   15   16   17                                                       
CONECT   16    2   15   18                                                  
CONECT   17   12   15   22                                                  
CONECT   18   13   16   22                                                  
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
3-Methyl-5-pentyl-2-furannonanoate	Generator
10,13-Epoxy-11-methyl-10,12-octadecadienoic acid	HMDB
10,13-Epoxy-11-methyloctadeca-10,12-dienoic acid	HMDB
Emod F-acid	HMDB
F2 acid	HMDB
Furan fatty acid F18	HMDB
MonoMe(9,5)	HMDB
10,13-Epoxy-11-methyloctadeca-10,12-dienoate	Generator

Chemical Formula

C₁₉H₃₂O₃

Average Mass

308.4556 Da

Monoisotopic Mass

308.23514 Da

IUPAC Name

9-(3-methyl-5-pentylfuran-2-yl)nonanoic acid

Traditional Name

9-(3-methyl-5-pentylfuran-2-yl)nonanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC(C)=C(CCCCCCCCC(O)=O)O1

InChI Identifier

InChI=1S/C19H32O3/c1-3-4-9-12-17-15-16(2)18(22-17)13-10-7-5-6-8-11-14-19(20)21/h15H,3-14H2,1-2H3,(H,20,21)

InChI Key

TUQVXFOSXOCQCM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Furanoid fatty acids

Alternative Parents

Substituents

Furanoid fatty acid
Medium-chain fatty acid
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	6.21	ALOGPS
logP	6.2	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	4.87	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	90.64 m³·mol⁻¹	ChemAxon
Polarizability	39.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031091

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB003096

KNApSAcK ID

Not Available

Chemspider ID

2342093

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3085134

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3-Methyl-5-pentyl-2-furannonanoic acid (NP0336593)

MOL for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

3D MOL for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

3D SDF for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

3D-SDF for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

PDB for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

3D PDB for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

SMILES for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

INCHI for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

Structure for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)

3D Structure for NP0336593 (3-Methyl-5-pentyl-2-furannonanoic acid)