NP-MRD: Showing NP-Card for geranyl formate (NP0272440)

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Record Information

Version

2.0

Created at

2022-09-08 19:04:07 UTC

Updated at

2022-09-08 19:04:07 UTC

NP-MRD ID

NP0272440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

geranyl formate

Description

(E)-geranyl formate, also known as geranyl methanoate or geraniol formic acid, belongs to the class of organic compounds known as fatty alcohol esters. geranyl formate is found in Citrus aurantium, Cleistopholis patens, Cryptomeria japonica, Daphne papyracea, Elsholtzia ciliata, Hamamelis virginiana, Helichrysum italicum, Lantana strigocamara, Pelargonium citronellum, Pelargonium graveolens, Pelargonium quercifolium, Rhododendron groenlandicum, Salvia sclarea and Vaccinium ashei. geranyl formate was first documented in 2010 (PMID: 20086122). These are ester derivatives of a fatty alcohol (E)-geranyl formate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 20939374) (PMID: 21644162) (PMID: 22287404) (PMID: 23027699).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 30  0  0  0  0  0  0  0  0999 V2000
   -3.5972   -1.2221   -1.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0027   -0.0815   -0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8374    0.7279    0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219    0.2115   -0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1288    1.3510    0.0307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0768    1.0337    1.0267 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1276    0.3367    0.5567 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0529   -1.0425    0.0098 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3379    0.8916    0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6183    0.3290    0.2317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6405   -0.9498   -0.2949 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8661   -1.4826   -0.6698 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9331   -0.8283   -0.5382 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5634   -1.5507   -0.8299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410   -2.1235   -1.2530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8161   -0.9280   -2.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4431    0.7316    1.4330 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9193    1.7924    0.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8552    0.2692    0.4682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1144   -0.3916   -1.4037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9553    1.8614    0.6183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8118    2.1664   -0.6856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5667    0.3956    1.8117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1793    1.9747    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7513   -1.7397    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0304   -1.4510    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1595   -1.0608   -1.0724 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3111    1.9227    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3343    0.3282    1.1099 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0841    1.0048   -0.5205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9246   -2.4763   -1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  6 23  1  0
  6 24  1  0
  5 21  1  0
  5 22  1  0
  4 20  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
M  END

HEADER    PROTEIN                                 22-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-16         0                                  
HETATM    1  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.390  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.540   5.335   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.540   2.667   0.000  0.00  0.00           O+0
HETATM   14  H   UNK     0       2.310  -1.334   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11   14                                                  
CONECT    8    7   13                                                       
CONECT    9   12   13                                                       
CONECT   10    1    2    5                                                  
CONECT   11    3    6    7                                                  
CONECT   12    9                                                            
CONECT   13    8    9                                                       
CONECT   14    7                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3,7-Dimethyl-2,6-octadien-1-ol, 1-formate	ChEBI
Formic acid, geraniol ester	ChEBI
Geraniol formate	ChEBI
Geranyl formate	ChEBI
Geranyl methanoate	ChEBI
Neryl formate	ChEBI
trans-3,7-Dimethyl-2,6-octadien-1-yl formate	ChEBI
trans-3,7-Dimethyl-2,6-octadien-1-yl methanoate	ChEBI
(2E)-3,7-Dimethyl-2,6-octadien-1-ol, 1-formic acid	Generator
Formate, geraniol ester	Generator
Geraniol formic acid	Generator
Geranyl formic acid	Generator
Geranyl methanoic acid	Generator
Neryl formic acid	Generator
trans-3,7-Dimethyl-2,6-octadien-1-yl formic acid	Generator
trans-3,7-Dimethyl-2,6-octadien-1-yl methanoic acid	Generator
(e)-Geranyl formic acid	Generator
[(2E)-3,7-Dimethylocta-2,6-dienyl] formic acid	Generator

Chemical Formula

C₁₁H₁₈O₂

Average Mass

182.2630 Da

Monoisotopic Mass

182.13068 Da

IUPAC Name

(2E)-3,7-dimethylocta-2,6-dien-1-yl formate

Traditional Name

geranyl formate

CAS Registry Number

Not Available

SMILES

[H]\C(COC=O)=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C11H18O2/c1-10(2)5-4-6-11(3)7-8-13-9-12/h5,7,9H,4,6,8H2,1-3H3/b11-7+

InChI Key

FQMZVFJYMPNUCT-YRNVUSSQSA-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
Citrus aurantium	LOTUS Database	35616633
Cleistopholis patens	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Daphne papyracea	LOTUS Database	35616633
Elsholtzia ciliata	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Lantana strigocamara	LOTUS Database	35616633
Pelargonium citronellum	LOTUS Database	35616633
Pelargonium graveolens	LOTUS Database	35616633
Pelargonium quercifolium	LOTUS Database	35616633
Rhododendron groenlandicum	LOTUS Database	35616633
Salvia sclarea	LOTUS Database	35616633
Vaccinium ashei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Monoterpenoid
Acyclic monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

formate ester (CHEBI:31648 )
Wax monoesters (LMFA07010611 )

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	3.73	ALOGPS
logP	2.89	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Basic)	-6.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	55.84 m³·mol⁻¹	ChemAxon
Polarizability	21.52 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

C12294

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282109

PDB ID

Not Available

ChEBI ID

31648

Good Scents ID

Not Available

References

General References

Yoder JA, Condon MR, Hart CE, Collier MH, Patrick KR, Benoit JB: Use of an alarm pheromone against ants for gaining access to aphid/scale prey by the red velvet mite Balaustium sp. (Erythraeidae) in a honeydew-rich environment. J Exp Biol. 2010 Feb 1;213(3):386-92. doi: 10.1242/jeb.035642. [PubMed:20086122 ]
Skelton AC, Cameron MM, Pickett JA, Birkett MA: Identification of neryl formate as the airborne aggregation pheromone for the American house dust mite and the European house dust mite (Acari: Epidermoptidae). J Med Entomol. 2010 Sep;47(5):798-804. doi: 10.1603/me09295. [PubMed:20939374 ]
Shimotori Y, Hattori K, Aoyama M, Miyakoshi T: Acyclic monoterpenes in tree essential oils as a shrinking agent for waste-expanded polystyrene. J Environ Sci Health A Tox Hazard Subst Environ Eng. 2011;46(8):813-6. doi: 10.1080/10934529.2011.579842. [PubMed:21644162 ]
Bayram I, Erten R, Bayram Y, Bulut G, Ozbek H: The hepatoprotective effects of dihydromyrcenol and geranyl formate in an experimental model of acute hepatic injury induced by the use of carbon tetrachloride. Turk J Gastroenterol. 2011 Dec;22(6):594-601. doi: 10.4318/tjg.2011.0312. [PubMed:22287404 ]
Boukhris M, Simmonds MS, Sayadi S, Bouaziz M: Chemical composition and biological activities of polar extracts and essential oil of rose-scented geranium, Pelargonium graveolens. Phytother Res. 2013 Aug;27(8):1206-13. doi: 10.1002/ptr.4853. Epub 2012 Oct 2. [PubMed:23027699 ]
LOTUS database [Link]

Showing NP-Card for geranyl formate (NP0272440)

MOL for NP0272440 (geranyl formate)

3D MOL for NP0272440 (geranyl formate)

3D SDF for NP0272440 (geranyl formate)

3D-SDF for NP0272440 (geranyl formate)

PDB for NP0272440 (geranyl formate)

3D PDB for NP0272440 (geranyl formate)

SMILES for NP0272440 (geranyl formate)

INCHI for NP0272440 (geranyl formate)

Structure for NP0272440 (geranyl formate)

3D Structure for NP0272440 (geranyl formate)