NP-MRD: Showing NP-Card for farnesoic acid (NP0325252)

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Record Information

Version

2.0

Created at

2022-09-12 05:51:32 UTC

Updated at

2022-09-12 05:51:33 UTC

NP-MRD ID

NP0325252

Secondary Accession Numbers

None

Natural Product Identification

Common Name

farnesoic acid

Description

Farnesoic acid, also known as farnesoate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. farnesoic acid is found in Conyza stricta and Solanum agrimoniifolium. farnesoic acid was first documented in 2002 (PMID: 11958988). Farnesoic acid is a very weakly acidic compound (based on its pKa) (PMID: 18242777) (PMID: 19919838) (PMID: 20965180) (PMID: 21187079).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 40  0  0  0  0  0  0  0  0999 V2000
   -5.1848    0.7616    0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1302   -0.6371   -0.4206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3424   -1.4860   -0.3921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9685   -1.0796   -0.8883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7485   -0.2270   -0.9175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7019   -0.9184   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -0.1636   -0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    1.2074    0.5174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6767   -0.7251   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899    0.0073   -0.4264 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9971   -0.7325    0.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2946   -0.0447    0.4661 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3999   -0.6318    1.2517 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4846    1.0808   -0.1742 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7589    1.7996   -0.1505 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7105    1.3456    0.4935 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8511    2.9934   -0.8706 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9279    1.4506   -0.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4875    0.8942    0.9505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2073    0.9936    0.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1185   -2.5061   -0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7105   -1.5136    0.6671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1621   -1.0609   -1.0368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9390   -2.1070   -1.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0287    0.7479   -0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3657   -0.1002   -1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5719   -1.9299   -0.4769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1091   -0.9494    0.9693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0162    1.9151   -0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3779    1.6061    0.7844 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2270    1.2731    1.4563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6800   -1.7353   -0.8654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648    0.0955   -1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373    1.0302   -0.0158 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5348   -0.8527    1.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1840   -1.7437   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2280   -0.9222    0.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7135    0.0077    2.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0665   -1.6009    1.7332 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6479    1.4944   -0.7510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2374    2.9638   -1.8033 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 17  1  0
 15 16  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 17 41  1  0
M  END

Farnesoic acid
  Mrv1572001071617252D          

 17 16  0  0  0  0            999 V2000
   -4.6207    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4773    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7628    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3806    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0950    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9529    1.4692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2385    2.7067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9062    2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095    2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484    1.8817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0484    2.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1918    1.4692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  9 17  2  0  0  0  0
  9  1  1  0  0  0  0
 17  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3 13  1  0  0  0  0
 13 16  2  0  0  0  0
 16  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  1  0  0  0  0
 11 15  2  0  0  0  0
 15  7  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  4  0  0  0
 13 14  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0325252

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)=CCCC(C)=CC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-12(2)7-5-8-13(3)9-6-10-14(4)11-15(16)17/h7,9,11H,5-6,8,10H2,1-4H3,(H,16,17)

> <INCHI_KEY>
WJHFZYAELPOJIV-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.885549951303325

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7,11-trimethyldodeca-2,6,10-trienoic acid

> <ALOGPS_LOGP>
4.68

> <JCHEM_LOGP>
4.482372109

> <ALOGPS_LOGS>
-3.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.12157483965426

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
74.8521

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
farnesoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Farnesoic acid                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -8.625   2.743   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.624   3.513   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.291   2.743   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.710   3.513   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.044   2.743   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.379   2.743   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.045   3.513   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.045   5.053   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -7.292   3.513   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -7.292   5.053   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.378   3.513   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.378   5.053   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.957   3.513   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.957   5.053   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.711   2.743   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.623   2.743   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.958   2.743   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   17    3                                                       
CONECT    3    2   13                                                       
CONECT    4   16    5                                                       
CONECT    5    4   11                                                       
CONECT    6    7                                                            
CONECT    7   15    6    8                                                  
CONECT    8    7                                                            
CONECT    9   17    1   10                                                  
CONECT   10    9                                                            
CONECT   11    5   15   12                                                  
CONECT   12   11                                                            
CONECT   13    3   16   14                                                  
CONECT   14   13                                                            
CONECT   15   11    7                                                       
CONECT   16   13    4                                                       
CONECT   17    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
Farnesoate	Generator
3,7,11-Trimethyl-2,6,10-dodecatrienoic acid	MeSH
Farnesenic acid	MeSH

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

3,7,11-trimethyldodeca-2,6,10-trienoic acid

Traditional Name

farnesoic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC(C)=CCCC(C)=CC(O)=O

InChI Identifier

InChI=1S/C15H24O2/c1-12(2)7-5-8-13(3)9-6-10-14(4)11-15(16)17/h7,9,11H,5-6,8,10H2,1-4H3,(H,16,17)

InChI Key

WJHFZYAELPOJIV-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

Species Name	Source	Reference
Conyza stricta	LOTUS Database	35616633
Solanum agrimoniifolium	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Farsesane sesquiterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Unsaturated fatty acid
Fatty acyl
Fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

alpha,beta-unsaturated monocarboxylic acid (CHEBI:36969 )
trienoic fatty acid (CHEBI:36969 )
methyl-branched fatty acid (CHEBI:36969 )

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	4.68	ALOGPS
logP	4.48	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.12	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.85 m³·mol⁻¹	ChemAxon
Polarizability	28.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

Not Available

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

93051

PDB ID

Not Available

ChEBI ID

36969

Good Scents ID

Not Available

References

General References

Kim S, Kim E, Shin DS, Kang H, Oh KB: Evaluation of morphogenic regulatory activity of farnesoic acid and its derivatives against Candida albicans dimorphism. Bioorg Med Chem Lett. 2002 Mar 25;12(6):895-8. doi: 10.1016/s0960-894x(02)00038-0. [PubMed:11958988 ]
Burtenshaw SM, Su PP, Zhang JR, Tobe SS, Dayton L, Bendena WG: A putative farnesoic acid O-methyltransferase (FAMeT) orthologue in Drosophila melanogaster (CG10527): relationship to juvenile hormone biosynthesis? Peptides. 2008 Feb;29(2):242-51. doi: 10.1016/j.peptides.2007.10.030. Epub 2007 Dec 7. [PubMed:18242777 ]
Tiu SH, Chan SM, Tobe SS: The effects of farnesoic acid and 20-hydroxyecdysone on vitellogenin gene expression in the lobster, Homarus americanus, and possible roles in the reproductive process. Gen Comp Endocrinol. 2010 Apr 1;166(2):337-45. doi: 10.1016/j.ygcen.2009.11.005. Epub 2009 Nov 15. [PubMed:19919838 ]
Chung SC, Kim TI, Ahn CH, Shin J, Oh KB: Candida albicans PHO81 is required for the inhibition of hyphal development by farnesoic acid. FEBS Lett. 2010 Nov 19;584(22):4639-45. doi: 10.1016/j.febslet.2010.10.026. Epub 2010 Oct 21. [PubMed:20965180 ]
Endo S, Matsunaga T, Ohta C, Soda M, Kanamori A, Kitade Y, Ohno S, Tajima K, El-Kabbani O, Hara A: Roles of rat and human aldo-keto reductases in metabolism of farnesol and geranylgeraniol. Chem Biol Interact. 2011 May 30;191(1-3):261-8. doi: 10.1016/j.cbi.2010.12.017. Epub 2010 Dec 25. [PubMed:21187079 ]
LOTUS database [Link]

Showing NP-Card for farnesoic acid (NP0325252)

MOL for NP0325252 (farnesoic acid)

3D MOL for NP0325252 (farnesoic acid)

3D SDF for NP0325252 (farnesoic acid)

3D-SDF for NP0325252 (farnesoic acid)

PDB for NP0325252 (farnesoic acid)

3D PDB for NP0325252 (farnesoic acid)

SMILES for NP0325252 (farnesoic acid)

INCHI for NP0325252 (farnesoic acid)

Structure for NP0325252 (farnesoic acid)

3D Structure for NP0325252 (farnesoic acid)