NP-MRD: Showing NP-Card for Geranylbenzoate (NP0085859)

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Record Information

Version

2.0

Created at

2022-04-29 06:18:19 UTC

Updated at

2022-04-29 06:18:19 UTC

NP-MRD ID

NP0085859

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Geranylbenzoate

Description

Geranyl benzoate belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Geranylbenzoate is found in Daphne papyracea and Acca sellowiana. Geranylbenzoate was first documented in 2015 (PMID: 27356375). Based on a literature review very few articles have been published on geranyl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 41 41  0  0  0  0  0  0  0  0999 V2000
   -4.8483    0.4830    2.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2399    0.8821    0.8294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0401    1.5806   -0.1924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9438    0.5963    0.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3098    0.9841   -0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9033   -0.1962   -1.4516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9309   -1.1340   -0.8610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -1.9289    0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2689   -1.3265   -1.4493 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2684   -2.2308   -0.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5009   -1.5575   -0.5989 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5838   -0.5363    0.3093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5445   -0.1652    0.8906 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8861    0.0798    0.5630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0104   -0.3503   -0.0915 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2562    0.2307    0.1434 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3213    1.2608    1.0636 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1923    1.7032    1.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704    1.1055    1.4746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9323    1.3651    2.8128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8669    0.0844    2.0080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2219   -0.2589    2.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0912    1.6550    0.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6138    2.5972   -0.3369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0466    1.0902   -1.1791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208    0.1071    1.4082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0766    1.6052   -1.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4831    1.7231   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5555    0.1791   -2.4581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8010   -0.8400   -1.7159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7814   -1.5554    1.2513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9372   -3.0022    0.2476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3375   -1.9950    0.4813 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4783   -0.7722   -2.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -2.9451   -0.1569 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5859   -2.8845   -1.7957 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9279   -1.1542   -0.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1091   -0.1382   -0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3069    1.6907    1.2224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856    2.5068    2.4381 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1099    1.4613    1.9998 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  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
 10 35  1  0
 10 36  1  0
 15 37  1  0
 16 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
M  END


  Mrv1652304292208182D          

 19 19  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  2 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085859

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\COC(=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H22O2/c1-14(2)8-7-9-15(3)12-13-19-17(18)16-10-5-4-6-11-16/h4-6,8,10-12H,7,9,13H2,1-3H3/b15-12+

> <INCHI_KEY>
YDVXYTIIPGKIJP-NTCAYCPXSA-N

> <FORMULA>
C17H22O2

> <MOLECULAR_WEIGHT>
258.361

> <EXACT_MASS>
258.161979948

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
30.632806788098854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3,7-dimethylocta-2,6-dien-1-yl benzoate

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
4.9976831446666665

> <ALOGPS_LOGS>
-4.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.899829867333711

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
81.00410000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3,7-dimethylocta-2,6-dien-1-yl benzoate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    2   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
(2E)-Geranyl benzoate	ChEBI
Benzoic acid geraniol ester	ChEBI
Benzoic acid geranyl ester	ChEBI
Benzoic acid, geraniol ester	ChEBI
Geraniol benzoate	ChEBI
trans-3,7-Dimethyl-2,6-octadien-1-yl benzoate	ChEBI
(2E)-Geranyl benzoic acid	Generator
Benzoate geraniol ester	Generator
Benzoate geranyl ester	Generator
Benzoate, geraniol ester	Generator
Geraniol benzoic acid	Generator
trans-3,7-Dimethyl-2,6-octadien-1-yl benzoic acid	Generator
Geranyl benzoic acid	Generator

Chemical Formula

C₁₇H₂₂O₂

Average Mass

258.3610 Da

Monoisotopic Mass

258.16198 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\COC(=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C17H22O2/c1-14(2)8-7-9-15(3)12-13-19-17(18)16-10-5-4-6-11-16/h4-6,8,10-12H,7,9,13H2,1-3H3/b15-12+

InChI Key

YDVXYTIIPGKIJP-NTCAYCPXSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Daphne papyracea	LOTUS Database	35616633
Feijoa sellowiana	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
Benzoate ester
Aromatic monoterpenoid
Benzoic acid or derivatives
Benzoyl
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	5.7	ALOGPS
logP	5	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-6.9	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	7	ChemAxon
Refractivity	81 m³·mol⁻¹	ChemAxon
Polarizability	30.63 Å³	ChemAxon
Number of Rings	1	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

C00055896

Chemspider ID

4509792

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5353011

PDB ID

Not Available

ChEBI ID

156234

Good Scents ID

rw1024871

References

General References

Huang TY, Weng YJ, Huang H, Xie QL, Yan CH, Zhao W: [Comparative Study on Volatile Constituents of Plumeriae Flos from Different Origins]. Zhong Yao Cai. 2015 Nov;38(11):2274-6. [PubMed:27356375 ]

Showing NP-Card for Geranylbenzoate (NP0085859)

MOL for NP0085859 (Geranylbenzoate)

3D MOL for NP0085859 (Geranylbenzoate)

3D SDF for NP0085859 (Geranylbenzoate)

3D-SDF for NP0085859 (Geranylbenzoate)

PDB for NP0085859 (Geranylbenzoate)

3D PDB for NP0085859 (Geranylbenzoate)

SMILES for NP0085859 (Geranylbenzoate)

INCHI for NP0085859 (Geranylbenzoate)

Structure for NP0085859 (Geranylbenzoate)

3D Structure for NP0085859 (Geranylbenzoate)