NP-MRD: Showing NP-Card for (2e,6e)-farnesoic acid (NP0256943)

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Record Information

Version

2.0

Created at

2022-09-07 21:55:57 UTC

Updated at

2022-09-07 21:55:57 UTC

NP-MRD ID

NP0256943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e,6e)-farnesoic acid

Description

Farnesoic acid, also known as (e,e)-farnesoate, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2e,6e)-farnesoic acid is found in Solanum agrimoniifolium. (2e,6e)-farnesoic acid was first documented in 2010 (PMID: 20965180). Farnesoic acid is a very weakly acidic compound (based on its pKa) (PMID: 22137909) (PMID: 23639754).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 40  0  0  0  0  0  0  0  0999 V2000
   -6.4807   -0.0066    0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9592   -0.0457    0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5705   -0.8355   -1.0616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2168    0.5910    0.9697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7792    0.7927    1.0704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9953    0.2998   -0.0763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5188    0.5220    0.1544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0097    1.8842    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -0.4933    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7797   -0.3322    0.4015 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6105   -0.8476   -0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0447   -0.6267   -0.4059 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6418   -1.2523    0.7992 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    0.1331   -1.1705 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2097    0.3985   -0.9016 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8721    1.1490   -1.6986 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9116   -0.1006    0.1659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8374    0.8230   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9117   -0.9640    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6744    0.2729    1.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1109   -1.8146   -0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9136   -0.3401   -1.7718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4986   -1.1088   -1.6787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7905    1.1055    1.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6360    1.9246    1.1951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4286    0.3645    2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2653    0.9372   -0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -0.7622   -0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5195    1.9226    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6279    2.2572   -0.4737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8615    2.5878    0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0892   -1.4817    0.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0849   -0.9578    1.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0266    0.7144    0.6731 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4124   -1.9346   -0.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3929   -0.3608   -1.7022 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9007   -1.8931    1.3367 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0069   -0.4365    1.4486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4888   -1.8957    0.5336 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3655    0.6006   -2.0676 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6358   -0.7903    0.0169 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

47205798
  Mrv1652308181800022D          

 17 16  0  0  0  0            999 V2000
   19.6964  -12.1934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9827  -10.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5516  -11.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2691  -12.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8379  -12.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6929  -11.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9828  -11.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1241  -11.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4066  -12.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9791  -12.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2617  -11.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5516  -10.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5479  -12.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8343  -11.7796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6929  -10.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1168  -12.1934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8343  -10.9558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  3 12  1  0  0  0  0
  4  7  1  0  0  0  0
  5  8  1  0  0  0  0
  6  9  2  0  0  0  0
  6 10  1  0  0  0  0
  6 15  1  0  0  0  0
  8  9  1  0  0  0  0
 10 11  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0256943

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CC\C(C)=C\C(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)/b13-9+,14-11+

> <INCHI_KEY>
WJHFZYAELPOJIV-IJFRVEDASA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
28.859931675731747

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E)-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>
farnesenic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 18-AUG-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 47205798                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-AUG-18         0                                  
HETATM    1  O   UNK     0      36.767 -22.761   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.434 -20.420   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      32.763 -21.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      34.102 -22.761   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.431 -22.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.427 -21.989   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      35.435 -21.989   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.098 -21.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      28.759 -22.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.094 -22.761   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.755 -21.989   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.763 -20.451   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.423 -22.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.091 -21.989   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.427 -20.451   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.751 -22.761   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.091 -20.451   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    5   12                                                  
CONECT    4    3    7                                                       
CONECT    5    3    8                                                       
CONECT    6    9   10   15                                                  
CONECT    7    1    2    4                                                  
CONECT    8    5    9                                                       
CONECT    9    6    8                                                       
CONECT   10    6   11                                                       
CONECT   11   10   13                                                       
CONECT   12    3                                                            
CONECT   13   11   14                                                       
CONECT   14   13   16   17                                                  
CONECT   15    6                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
(2-trans-6-trans) Farnesoic acid	ChEBI
(2E,6E)-Farnesenic acid	ChEBI
(2E,6E)-Farnesic acid	ChEBI
(2E,6E)-Farnesylic acid	ChEBI
(e,e)-Farnesoic acid	ChEBI
all-trans-Farnesoic acid	ChEBI
trans,trans-Farnesoic acid	ChEBI
(2E,6E)-Farnesoate	Kegg
(2-trans-6-trans) Farnesoate	Generator
(2E,6E)-Farnesenate	Generator
(2E,6E)-Farnesate	Generator
(2E,6E)-Farnesylate	Generator
(e,e)-Farnesoate	Generator
all-trans-Farnesoate	Generator
trans,trans-Farnesoate	Generator
(2E,6E)-Farnesoic acid	Generator
Farnesoate	Generator
3,7,11-Trimethyl-2,6,10-dodecatrienoic acid	MeSH
Farnesenic acid	MeSH
Farnesoic acid	ChEBI

Chemical Formula

C₁₅H₂₄O₂

Average Mass

236.3550 Da

Monoisotopic Mass

236.17763 Da

IUPAC Name

(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienoic acid

Traditional Name

farnesenic acid

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CC\C(C)=C\C(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)/b13-9+,14-11+

InChI Key

WJHFZYAELPOJIV-IJFRVEDASA-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
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

farnesoic acid (CHEBI:84162 )

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	28.86 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

C16502

BioCyc ID

CPD-12585

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5275507

PDB ID

Not Available

ChEBI ID

84162

Good Scents ID

Not Available

References

General References

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 ]
Tiu SH, Hult EF, Yagi KJ, Tobe SS: Farnesoic acid and methyl farnesoate production during lobster reproduction: possible functional correlation with retinoid X receptor expression. Gen Comp Endocrinol. 2012 Jan 15;175(2):259-69. doi: 10.1016/j.ygcen.2011.11.016. Epub 2011 Nov 23. [PubMed:22137909 ]
Rivera-Perez C, Nouzova M, Clifton ME, Garcia EM, LeBlanc E, Noriega FG: Aldehyde dehydrogenase 3 converts farnesal into farnesoic acid in the corpora allata of mosquitoes. Insect Biochem Mol Biol. 2013 Aug;43(8):675-82. doi: 10.1016/j.ibmb.2013.04.002. Epub 2013 Apr 29. [PubMed:23639754 ]
LOTUS database [Link]

Showing NP-Card for (2e,6e)-farnesoic acid (NP0256943)

MOL for NP0256943 ((2e,6e)-farnesoic acid)

3D MOL for NP0256943 ((2e,6e)-farnesoic acid)

3D SDF for NP0256943 ((2e,6e)-farnesoic acid)

3D-SDF for NP0256943 ((2e,6e)-farnesoic acid)

PDB for NP0256943 ((2e,6e)-farnesoic acid)

3D PDB for NP0256943 ((2e,6e)-farnesoic acid)

SMILES for NP0256943 ((2e,6e)-farnesoic acid)

INCHI for NP0256943 ((2e,6e)-farnesoic acid)

Structure for NP0256943 ((2e,6e)-farnesoic acid)

3D Structure for NP0256943 ((2e,6e)-farnesoic acid)