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Showing NP-Card for 2,5,5-Trimethyl-3,6-heptadien-2-ol (NP0057298)

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Record Information
Version2.0
Created at2022-04-28 02:46:43 UTC
Updated at2022-04-28 02:46:43 UTC
NP-MRD IDNP0057298
Secondary Accession NumbersNone
Natural Product Identification
Common Name2,5,5-Trimethyl-3,6-heptadien-2-ol
DescriptionYomogi alcohol belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). 2,5,5-Trimethyl-3,6-heptadien-2-ol is found in Achillea millefolium, Artemisia argyi , Artemisia douglasiana, Artemisia feddei, Artemisia herba-alba, Artemisia judaica, Daucus carota, Santolina chamaecyparissus, Santolina corsica Jordan et Fourr and Tanacetum vulgare. 2,5,5-Trimethyl-3,6-heptadien-2-ol was first documented in 2012 (PMID: 23285821). Based on a literature review a small amount of articles have been published on Yomogi alcohol (PMID: 35170197) (PMID: 34451766) (PMID: 26876676) (PMID: 25829614).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)


  Mrv1652304282204462D          

 11 10  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    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
   -0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  3 10  1  0  0  0  0
  3 11  1  0  0  0  0
M  END
Download

3D MOL for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
   -2.9316    1.8420    0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7320    1.3900    0.5485 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4905    0.0335    0.0273 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6265   -1.0292    1.0973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4330   -0.2308   -1.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1161   -0.0367   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8632   -0.4708    0.3018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2190   -0.5068   -0.3176 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3883    0.7946   -1.0746 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2466   -0.6079    0.7773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2458   -1.5793   -1.1879 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0322    2.8432    1.2398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7728    1.1794    0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8887    2.0555    0.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705   -1.8738    0.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6659   -1.3958    1.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2347   -0.6078    2.0370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9080   -0.0587   -2.0962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6614   -1.3173   -1.1028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3126    0.4079   -1.0938 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0720    0.2646   -1.5193 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6704   -0.7711    1.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8287    1.6223   -0.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    1.1151   -1.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    0.6495   -2.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2794    0.3756    1.2875 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9261   -1.4079    1.4854 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2271   -0.8095    0.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3309   -1.8695   -1.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8 10  1  0
  8 11  1  6
  8  7  1  0
  7  6  2  0
  6  3  1  0
  3  4  1  1
  3  5  1  0
  3  2  1  0
  2  1  2  3
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
  7 22  1  0
  6 21  1  0
  4 15  1  0
  4 16  1  0
  4 17  1  0
  5 18  1  0
  5 19  1  0
  5 20  1  0
  2 14  1  0
  1 12  1  0
  1 13  1  0
M  END
Download

3D SDF for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)


  Mrv1652304282204462D          

 11 10  0  0  0  0            999 V2000
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4289    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
   -0.8250   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    0.3020    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  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  3 10  1  0  0  0  0
  3 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057298

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-6-9(2,3)7-8-10(4,5)11/h6-8,11H,1H2,2-5H3/b8-7+

> <INCHI_KEY>
CSMMFGCGBLZIJE-BQYQJAHWSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.852576577077983

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-2,5,5-trimethylhepta-3,6-dien-2-ol

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.4686750023333333

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.687238914848816

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6234016986451278

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
50.4243

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.23e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-2,5,5-trimethylhepta-3,6-dien-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)

Download
PDB for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)
HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.080   2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   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  -2.667   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.104  -0.564   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.564  -2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.644   0.564   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10   11                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
CONECT   10    3                                                            
CONECT   11    3                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END

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3D PDB for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)
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SMILES for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)
CC(C)(O)\C=C\C(C)(C)C=C
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INCHI for NP0057298 (2,5,5-Trimethyl-3,6-heptadien-2-ol)
InChI=1S/C10H18O/c1-6-9(2,3)7-8-10(4,5)11/h6-8,11H,1H2,2-5H3/b8-7+
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SynonymsNot Available
Chemical FormulaC10H18O
Average Mass154.2530 Da
Monoisotopic Mass154.13577 Da
IUPAC Name(3E)-2,5,5-trimethylhepta-3,6-dien-2-ol
Traditional Name(3E)-2,5,5-trimethylhepta-3,6-dien-2-ol
CAS Registry NumberNot Available
SMILES
CC(C)(O)\C=C\C(C)(C)C=C
InChI Identifier
InChI=1S/C10H18O/c1-6-9(2,3)7-8-10(4,5)11/h6-8,11H,1H2,2-5H3/b8-7+
InChI KeyCSMMFGCGBLZIJE-BQYQJAHWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumLOTUS Database
Artemisia argyiPlant
Artemisia douglasianaLOTUS Database
Artemisia feddeiPlant
Artemisia herba-albaLOTUS Database
Artemisia judaicaLOTUS Database
Daucus carotaLOTUS Database
Santolina chamaecyparissusLOTUS Database
Santolina corsica Jordan et FourrPlant
Tanacetum vulgareLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).
KingdomOrganic compounds  
Super ClassOrganic oxygen compounds  
ClassOrganooxygen compounds  
Sub ClassAlcohols and polyols  
Direct ParentTertiary alcohols  
Alternative Parents
Substituents
  • Tertiary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP2.79ALOGPS
logP2.47ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)17.69ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity50.42 m³·mol⁻¹ChemAxon
Polarizability18.85 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 IDC00010371  
Chemspider ID4474725  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5315406  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Acimovic M, Jeremic JS, Todosijevic M, Kiprovski B, Vidovic S, Vladic J, Pezo L: Comparative Study of the Essential Oil and Hydrosol Composition of Sweet Wormwood (Artemisia annua L.) from Serbia. Chem Biodivers. 2022 Mar;19(3):e202100954. doi: 10.1002/cbdv.202100954. Epub 2022 Feb 15. [PubMed:35170197  ] 
  2. Elhawary EA, Mostafa NM, Labib RM, Singab AN: Metabolomic Profiles of Essential Oils from Selected Rosa Varieties and Their Antimicrobial Activities. Plants (Basel). 2021 Aug 20;10(8). pii: plants10081721. doi: 10.3390/plants10081721. [PubMed:34451766  ] 
  3. Polatoglu K, Arsal S, Demirci B, Can Baser KH: Unexpected Irregular Monoterpene "Yomogi Alcohol" in the Volatiles of the Lathyrus L. species (Leguminosae) of Cyprus. J Oleo Sci. 2016;65(3):241-9. doi: 10.5650/jos.ess15165. Epub 2016 Feb 15. [PubMed:26876676  ] 
  4. Kasrati A, Alaoui Jamali C, Bekkouche K, Wohlmuth H, Leach D, Abbad A: Comparative evaluation of antioxidant and insecticidal properties of essential oils from five Moroccan aromatic herbs. J Food Sci Technol. 2015 Apr;52(4):2312-9. doi: 10.1007/s13197-014-1284-z. Epub 2014 Feb 16. [PubMed:25829614  ] 
  5. Masoudi S, Rustaiyan A, Vahedi M: Volatile oil constituents of different parts of Artemisia chamaemelifolia and the composition and antibacterial activity of the aerial parts of A. turcomanica from Iran. Nat Prod Commun. 2012 Nov;7(11):1519-22. [PubMed:23285821  ]