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Showing NP-Card for geranyl acetate (NP0205552)

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Record Information
Version2.0
Created at2022-09-05 01:29:17 UTC
Updated at2022-09-05 01:29:17 UTC
NP-MRD IDNP0205552
Secondary Accession NumbersNone
Natural Product Identification
Common Namegeranyl acetate
DescriptionGeranyl acetate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. geranyl acetate is found in Abies sibirica, Abutilon indicum, Achillea nobilis, Acorus calamus, Aframomum angustifolium, Aloysia citrodora, Alpinia chinensis, Alpinia galanga, Antidesma laciniatum, Artemisia judaica, Artemisia schmidtiana, Artemisia scoparia, Artemisia sericea, Asarum canadense, Baccharis dracunculifolia, Baccharis salicina, Bellis perennis, Blepharocalyx salicifolius, Boswellia sacra, Bothriochloa bladhii, Cananga odorata, Ceratitis capitata, Chaerophyllum bulbosum, Chaerophyllum macrospermum, Cinnamomum burmannii, Cinnamomum osmophloeum, Cinnamomum verum, Citrus aurantium, Citrus iyo, Citrus junos, Citrus limon, Citrus maxima, Citrus medica, Citrus natsudaidai, Citrus reticulata, Citrus sinensis, Citrus trifoliata, Citrus unshiu, Citrus wilsonii, Coriandrum sativum, Cymbopogon citratus, Cymbopogon distans, Cymbopogon flexuosus, Cymbopogon martinii, Cymbopogon nardus, Cymbopogon winterianus, Daphne odora, Daucus carota, Dracocephalum moldavica, Dysphania graveolens, Elettaria cardamomum, Elionurus muticus, Elsholtzia ciliata, Eupatorium fortunei, Helichrysum amorginum, Heracleum antasiaticum, Heracleum dissectum, Houttuynia cordata, Juniperus communis, Lantana camara, Lantana strigocamara, Larix laricina, Laurus nobilis, Lavandula angustifolia, Rhododendron tomentosum, Lepechinia chamaedryoides, Leptospermum scoparium, Levisticum officinale, Lindera umbellata, Machilus japonica, Malus domestica, Mentha piperita, Micromeria biflora, Mikania cordifolia, Mutisia spinosa, Myrtus communis, Nepeta nepetella, Nepeta racemosa, Nepeta tuberosa, Origanum acutidens, Origanum majorana, Origanum vulgare, Pandanus tectorius, Pectis elongata, Pelargonium quercifolium, Picea schrenkiana, Pimenta racemosa, Pinus halepensis, Piper aduncum, Plectranthus glabratus, Rhododendron groenlandicum, Rhododendron mucronulatum, Rosa damascena, Rosa gallica, Salvia absconditiflora, Salvia fruticosa, Salvia sclarea, Saxifraga stolonifera, Scytosiphon lomentaria, Solidago odora, Spondias mombin, Stachys recta, Syzygium nervosum, Tanacetum longifolium, Thapsia maxima, Thapsia villosa, Thuja occidentalis, Thymus vulgaris, Tordylium apulum, Zanthoxylum gilletii, Zanthoxylum simulans and Zingiber officinale. geranyl acetate was first documented in 2015 (PMID: 25698327). Geranyl acetate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0205552 (geranyl acetate)


  Mrv1652309272007392D          

 14 13  0  0  0  0            999 V2000
10006.959610006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.675210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.388810006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.104410006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.818010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.533610006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.818010007.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.244710006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.530010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.815010006.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.100210006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.385410006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.100210007.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.959610007.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
Download

3D MOL for NP0205552 (geranyl acetate)

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3D SDF for NP0205552 (geranyl acetate)

  Mrv1652309272007392D          

 14 13  0  0  0  0            999 V2000
10006.959610006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.675210006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.388810006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.104410006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.818010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.533610006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.818010007.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.244710006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.530010006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.815010006.3509    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.100210006.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.385410006.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.100210007.5881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.959610007.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  2  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0205552

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8+

> <INCHI_KEY>
HIGQPQRQIQDZMP-DHZHZOJOSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.29

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
23.609741514763815

> <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 acetate

> <ALOGPS_LOGP>
4.11

> <JCHEM_LOGP>
2.9435087063333336

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004434726067085

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
60.333600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
geranyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0205552 (geranyl acetate)
Download
PDB for NP0205552 (geranyl acetate)
HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8679.6588679.290   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8680.9948678.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8682.3268679.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8683.6628678.522   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8684.9948679.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8686.3298678.522   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8684.9948680.831   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8678.3248678.522   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8676.9898679.290   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8675.6558678.522   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8674.3208679.290   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8672.9868678.522   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8674.3208680.831   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8679.6588680.831   0.000  0.00  0.00           C+0
CONECT    1    2    8   14                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

Download
3D PDB for NP0205552 (geranyl acetate)
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SMILES for NP0205552 (geranyl acetate)
CC(C)=CCC\C(C)=C\COC(C)=O
Download
INCHI for NP0205552 (geranyl acetate)
InChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8+
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View in JSmol
Synonyms
ValueSource
trans-3,7-Dimethyl-2,6-octadien-1-yl acetateChEBI
trans-3,7-Dimethyl-2,6-octadien-1-yl acetic acidGenerator
Geranyl acetic acidGenerator
Geraniol acetate, (Z)-isomerMeSH
Geraniol acetate, (e)-isomerMeSH
Nerol acetateMeSH
Neryl acetateMeSH
Geraniol acetateMeSH
(E)-3,7-Dimethyl-2,6-octadien-1-ol acetatePhytoBank
(E)-3,7-Dimethyl-2,6-octadienyl acetatePhytoBank
3,7-Dimethyl-2,6-octadien-1-ol acetatePhytoBank
Acetic acid (2E)-3,7-dimethyl-2,6-octadienyl esterPhytoBank
Acetic acid geraniol esterPhytoBank
Acetic acid geranyl esterPhytoBank
Geranyl ethanoatePhytoBank
trans-1-Acetoxy-3,7-dimethyl-2,6-octadienePhytoBank
trans-Geranyl acetatePhytoBank
beta-Geranyl acetatePhytoBank
β-Geranyl acetatePhytoBank
Chemical FormulaC12H20O2
Average Mass196.2900 Da
Monoisotopic Mass196.14633 Da
IUPAC Name(2E)-3,7-dimethylocta-2,6-dien-1-yl acetate
Traditional Namegeranyl acetate
CAS Registry NumberNot Available
SMILES
CC(C)=CCC\C(C)=C\COC(C)=O
InChI Identifier
InChI=1S/C12H20O2/c1-10(2)6-5-7-11(3)8-9-14-12(4)13/h6,8H,5,7,9H2,1-4H3/b11-8+
InChI KeyHIGQPQRQIQDZMP-DHZHZOJOSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Abies sibiricaLOTUS Database
Abutilon indicumLOTUS Database
Achillea nobilisLOTUS Database
Acorus calamusLOTUS Database
Aframomum angustifoliumLOTUS Database
Aloysia citrodoraLOTUS Database
Alpinia chinensisLOTUS Database
Alpinia galangaLOTUS Database
Antidesma laciniatumLOTUS Database
Artemisia judaicaLOTUS Database
Artemisia schmidtianaLOTUS Database
Artemisia scopariaLOTUS Database
Artemisia sericeaLOTUS Database
Asarum canadenseLOTUS Database
Baccharis dracunculifoliaLOTUS Database
Baccharis salicinaLOTUS Database
Bellis perennisLOTUS Database
Blepharocalyx salicifoliusLOTUS Database
Boswellia sacraLOTUS Database
Bothriochloa bladhiiLOTUS Database
Cananga odorataLOTUS Database
Ceratitis capitataLOTUS Database
Chaerophyllum bulbosumLOTUS Database
Chaerophyllum macrospermumLOTUS Database
Cinnamomum burmanniLOTUS Database
Cinnamomum osmophloeumLOTUS Database
Cinnamomum verumLOTUS Database
Citrus aurantiumLOTUS Database
Citrus iyoLOTUS Database
Citrus junosLOTUS Database
Citrus limonLOTUS Database
Citrus maximaLOTUS Database
Citrus medicaLOTUS Database
Citrus natsudaidaiLOTUS Database
Citrus reticulataLOTUS Database
Citrus sinensisLOTUS Database
Citrus trifoliataLOTUS Database
Citrus unshiuLOTUS Database
Citrus wilsoniiLOTUS Database
Coriandrum sativumLOTUS Database
Cymbopogon citratusLOTUS Database
Cymbopogon distansLOTUS Database
Cymbopogon flexuosusLOTUS Database
Cymbopogon martiniiLOTUS Database
Cymbopogon nardusLOTUS Database
Cymbopogon winterianusLOTUS Database
Daphne odoraLOTUS Database
Daucus carotaLOTUS Database
Dracocephalum moldavicaLOTUS Database
Dysphania graveolensLOTUS Database
Elettaria cardamomumLOTUS Database
Elionurus muticusLOTUS Database
Elsholtzia ciliataLOTUS Database
Eupatorium fortuneiLOTUS Database
Helichrysum amorginumLOTUS Database
Heracleum antasiaticumLOTUS Database
Heracleum dissectumLOTUS Database
Houttuynia cordataLOTUS Database
Juniperus communisLOTUS Database
Lantana camaraLOTUS Database
Lantana strigocamaraLOTUS Database
Larix laricinaLOTUS Database
Laurus nobilisLOTUS Database
Lavandula angustifoliaLOTUS Database
Ledum palustreLOTUS Database
Lepechinia chamaedryoidesLOTUS Database
Leptospermum scopariumLOTUS Database
Levisticum officinaleLOTUS Database
Lindera umbellataLOTUS Database
Machilus japonicaLOTUS Database
Malus domesticaLOTUS Database
Mentha piperitaLOTUS Database
Micromeria bifloraLOTUS Database
Mikania cordifoliaLOTUS Database
Mutisia spinosaLOTUS Database
Myrtus communisLOTUS Database
Nepeta nepetellaLOTUS Database
Nepeta racemosaLOTUS Database
Nepeta tuberosaLOTUS Database
Origanum acutidensLOTUS Database
Origanum majoranaLOTUS Database
Origanum vulgareLOTUS Database
Pandanus tectoriusLOTUS Database
Pectis elongataLOTUS Database
Pelargonium quercifoliumLOTUS Database
Picea schrenkianaLOTUS Database
Pimenta racemosaLOTUS Database
Pinus halepensisLOTUS Database
Piper aduncumLOTUS Database
Plectranthus glabratusLOTUS Database
Rhododendron groenlandicumLOTUS Database
Rhododendron mucronulatumLOTUS Database
Rosa damascenaLOTUS Database
Rosa gallicaLOTUS Database
Salvia absconditifloraLOTUS Database
Salvia fruticosaLOTUS Database
Salvia sclareaLOTUS Database
Saxifraga stoloniferaLOTUS Database
Scytosiphon lomentariaLOTUS Database
Solidago odoraLOTUS Database
Spondias mombinLOTUS Database
Stachys rectaLOTUS Database
Syzygium nervosumLOTUS Database
Tanacetum longifoliumLOTUS Database
Thapsia maximaLOTUS Database
Thapsia villosaLOTUS Database
Thuja occidentalisLOTUS Database
Thymus vulgarisLOTUS Database
Tordylium apulumLOTUS Database
Zanthoxylum gilletiiLOTUS Database
Zanthoxylum simulansLOTUS Database
Zingiber officinaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassFatty alcohol esters  
Direct ParentFatty 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.11ALOGPS
logP2.94ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity60.33 m³·mol⁻¹ChemAxon
Polarizability23.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00003046  
Chemspider IDNot Available
KEGG Compound IDC09861  
BioCyc IDCPD-9758  
BiGG IDNot Available
Wikipedia LinkGeranyl_acetate  
METLIN IDNot Available
PubChem Compound1549026  
PDB IDNot Available
ChEBI ID5331  
Good Scents IDNot Available
References
General References
  1. Zhang Q, Tiefenbacher K: Terpene cyclization catalysed inside a self-assembled cavity. Nat Chem. 2015 Mar;7(3):197-202. doi: 10.1038/nchem.2181. Epub 2015 Feb 16. [PubMed:25698327  ] 
  2. LOTUS database [Link]