Np mrd loader

Showing NP-Card for 3,7-dimethyl-2,6-octadienal (NP0238495)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-09-06 21:54:06 UTC
Updated at2022-09-06 21:54:06 UTC
NP-MRD IDNP0238495
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,7-dimethyl-2,6-octadienal
DescriptionCitral, also known as cis,trans-citral, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. 3,7-dimethyl-2,6-octadienal is found in Aleuroglyphus ovatus, Aloysia citrodora, Aloysia triphylla, Artemisia fragrans, Backhousia citriodora, Bunium persicum, Bupleurum fruticescens, Centaurea benedicta, Citrus aurantiifolia, Citrus junos, Citrus limon, Citrus maxima, Citrus paradisi, Citrus wilsonii, Cymbopogon citratus, Cymbopogon distans, Cymbopogon flexuosus, Dracocephalum kotschyi, Humulus lupulus, Lantana camara, Lippia alba, Litsea cubeba, Magnolia salicifolia, Melissa officinalis, Monarda fistulosa, Nepeta cataria, Ocimum basilicum, Perilla frutescens, Pieris napi, Pistacia atlantica, Rosa gallica, Solanum tuberosum, Suidasia medanensis, Thymus pulegioides and Zingiber officinale. 3,7-dimethyl-2,6-octadienal was first documented in 2011 (PMID: 20303242). Citral is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 21174108) (PMID: 21209212) (PMID: 21316719) (PMID: 21366054).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0238495 (3,7-dimethyl-2,6-octadienal)


  Mrv1533004161520322D          

 11 10  0  0  0  0            999 V2000
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
Download

3D MOL for NP0238495 (3,7-dimethyl-2,6-octadienal)

     RDKit          3D

 27 26  0  0  0  0  0  0  0  0999 V2000
   -4.0061    0.7845    0.0847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6537    0.1512    0.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5191   -1.3262    0.0042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    0.8682    0.4130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2404    0.2381    0.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7228    0.7763   -0.5351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0555    0.1346   -0.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2316   -1.3206   -0.5918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1138    0.8758   -0.1911 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4477    0.3117   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291   -0.9011   -0.1924 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    1.7810   -0.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4604    0.9416    1.0809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7141    0.1788   -0.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -1.5667   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0417   -1.7920    0.9010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5314   -1.7602   -0.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6637    1.9293    0.5387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3399   -0.8629    0.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502    0.3293    1.5204 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3486    0.5644   -1.5575 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8073    1.8569   -0.3947 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6420   -1.7574    0.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8956   -1.6198   -1.4136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2326   -1.7626   -0.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9559    1.9559   -0.0761 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2797    0.9919    0.1238 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  2  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
M  END
Download

3D SDF for NP0238495 (3,7-dimethyl-2,6-octadienal)


  Mrv1533004161520322D          

 11 10  0  0  0  0            999 V2000
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  2  0  0  0  0
  6 10  1  0  0  0  0
  2 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0238495

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3

> <INCHI_KEY>
WTEVQBCEXWBHNA-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.660159596081563

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,7-dimethylocta-2,6-dienal

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
2.664041581666667

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.056096067340819

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
50.12409999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.00e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyl-2,6-octadienal

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0238495 (3,7-dimethyl-2,6-octadienal)

Download
PDB for NP0238495 (3,7-dimethyl-2,6-octadienal)
HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6                                                            
CONECT   11    2                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

Download
3D PDB for NP0238495 (3,7-dimethyl-2,6-octadienal)
Download
SMILES for NP0238495 (3,7-dimethyl-2,6-octadienal)
CC(C)=CCCC(C)=CC=O
Download
INCHI for NP0238495 (3,7-dimethyl-2,6-octadienal)
InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3
Download
View in JSmol
Synonyms
ValueSource
3,7-Dimethyl-2,6-octadienalChEBI
cis,trans-CitralChEBI
(Z)-CitralMeSH
NeralMeSH
(e)-CitralMeSH
GeranialMeSH
Citral aMeSH
Citral bMeSH
Chemical FormulaC10H16O
Average Mass152.2370 Da
Monoisotopic Mass152.12012 Da
IUPAC Name3,7-dimethylocta-2,6-dienal
Traditional Name3,7-dimethyl-2,6-octadienal
CAS Registry NumberNot Available
SMILES
CC(C)=CCCC(C)=CC=O
InChI Identifier
InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3
InChI KeyWTEVQBCEXWBHNA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aleuroglyphus ovatusLOTUS Database
Aloysia citrodoraLOTUS Database
Aloysia triphyllaLOTUS Database
Artemisia fragransLOTUS Database
Backhousia citriodoraLOTUS Database
Bunium persicumLOTUS Database
Bupleurum fruticescensLOTUS Database
Centaurea benedictaLOTUS Database
Citrus aurantiifoliaLOTUS Database
Citrus junosLOTUS Database
Citrus limonLOTUS Database
Citrus maximaLOTUS Database
Citrus paradisiLOTUS Database
Citrus wilsoniiLOTUS Database
Cymbopogon citratusLOTUS Database
Cymbopogon distansLOTUS Database
Cymbopogon flexuosusLOTUS Database
Dracocephalum kotschyiLOTUS Database
Humulus lupulusLOTUS Database
Lantana camaraLOTUS Database
Lippia albaLOTUS Database
Litsea cubebaLOTUS Database
Magnolia salicifoliaLOTUS Database
Melissa officinalisLOTUS Database
Monarda fistulosaLOTUS Database
Nepeta catariaLOTUS Database
Ocimum basilicumLOTUS Database
Perilla frutescensLOTUS Database
Pieris napiLOTUS Database
Pistacia atlanticaLOTUS Database
Rosa gallicaLOTUS Database
Solanum tuberosumLOTUS Database
Suidasia medanensisLOTUS Database
Thymus pulegioidesLOTUS Database
Zingiber officinaleLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassPrenol lipids  
Sub ClassMonoterpenoids  
Direct ParentAcyclic monoterpenoids  
Alternative Parents
Substituents
  • Acyclic monoterpenoid
    • 

  • Medium-chain aldehyde
    • 

  • Enal
    • 

  • Alpha,beta-unsaturated aldehyde
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Aldehyde
    • 

  • 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
logP3.37ALOGPS
logP2.66ChemAxon
logS-2.6ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.12 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitral  
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID23316  
Good Scents IDNot Available
References
General References
  1. Koussoulakou DS, Margaritis LH, Koussoulakos SL: Antagonists of retinoic acid and BMP4 affect fetal mouse osteogenesis and odontoblast differentiation. Pathophysiology. 2011 Apr;18(2):103-9. doi: 10.1016/j.pathophys.2010.02.001. Epub 2010 Mar 29. [PubMed:20303242  ] 
  2. Gonzalez-Audino P, Picollo MI, Gallardo A, Toloza A, Vassena C, Mougabure-Cueto G: Comparative toxicity of oxygenated monoterpenoids in experimental hydroalcoholic lotions to permethrin-resistant adult head lice. Arch Dermatol Res. 2011 Jul;303(5):361-6. doi: 10.1007/s00403-010-1110-z. Epub 2010 Dec 21. [PubMed:21174108  ] 
  3. Ukhanov K, Brunert D, Corey EA, Ache BW: Phosphoinositide 3-kinase-dependent antagonism in mammalian olfactory receptor neurons. J Neurosci. 2011 Jan 5;31(1):273-80. doi: 10.1523/JNEUROSCI.3698-10.2011. [PubMed:21209212  ] 
  4. Aiemsaard J, Aiumlamai S, Aromdee C, Taweechaisupapong S, Khunkitti W: The effect of lemongrass oil and its major components on clinical isolate mastitis pathogens and their mechanisms of action on Staphylococcus aureus DMST 4745. Res Vet Sci. 2011 Dec;91(3):e31-7. doi: 10.1016/j.rvsc.2011.01.012. Epub 2011 Feb 12. [PubMed:21316719  ] 
  5. Gupta S, Pandotra P, Ram G, Anand R, Gupta AP, Husain K, Bedi YS, Mallavarapu GR: Composition of a monoterpenoid-rich essential oil from the rhizome of Zingiber officinale from north western Himalayas. Nat Prod Commun. 2011 Jan;6(1):93-6. [PubMed:21366054  ] 
  6. LOTUS database [Link]