NP-MRD: Showing NP-Card for α-ionol (NP0261240)

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Record Information

Version

1.0

Created at

2022-09-08 03:37:44 UTC

Updated at

2022-09-08 03:37:44 UTC

NP-MRD ID

NP0261240

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-ionol

Description

4,7-Megastigmadien-9-ol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 4,7-Megastigmadien-9-ol is an extremely weak basic (essentially neutral) compound (based on its pKa). 4,7-Megastigmadien-9-ol is a sweet, floral, and ionone tasting compound. α-ionol is found in Melissa officinalis. It was first documented in 2000 (PMID: 11413487). Outside of the human body, (PMID: 16902246) (PMID: 17374880) (PMID: 20044567).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 36  0  0  0  0  0  0  0  0999 V2000
   -0.8140    2.6484   -1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1645    1.4143   -0.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0600    1.4616    0.6455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4741    0.3078    1.4317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159   -0.8291    1.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260   -1.0360   -0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4914   -1.1380   -0.8710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -2.2908   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4259    0.1625   -0.7107 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9657    0.3750   -0.3472 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365   -0.3338    0.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1471    0.0737    0.6741 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9841   -0.3127   -0.5312 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2671    1.4402    0.8938 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0596    3.1262   -0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5356    2.4272   -2.0883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6327    3.4016   -1.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5377    2.4318    0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4256    0.6285    2.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5128    0.0030    1.1701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7054   -0.7522    2.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0904   -1.7606    1.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2318   -1.6326   -0.2225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3980   -1.7441   -1.7851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8694   -0.1138   -1.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0180   -3.0117   -1.0588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5299   -2.1852   -1.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2180   -2.8735    0.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5166    0.1250   -1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578    1.2588   -0.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685   -1.1915    0.9310 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5836   -0.4423    1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9962   -0.6256   -0.2669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4757   -1.1849   -1.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9333    0.5335   -1.2409 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6710    1.6394    1.7656 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  2  1  0
  2  1  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 12 32  1  1
 14 36  1  0
 11 31  1  0
 10 30  1  0
  9 29  1  6
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
M  END


  Mrv0541 05061310362D          

 14 14  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  2  0  0  0  0
  9  5  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  2  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13  3  1  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0261240

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)\C=C\C1C(C)=CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,11-12,14H,5,9H2,1-4H3/b8-7+

> <INCHI_KEY>
PWDOJWCZWKWKSE-BQYQJAHWSA-N

> <FORMULA>
C13H22O

> <MOLECULAR_WEIGHT>
194.3132

> <EXACT_MASS>
194.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.928486073663755

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-ol

> <ALOGPS_LOGP>
4.10

> <JCHEM_LOGP>
3.085956459

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.911424557736087

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9627428984462352

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
63.089000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   3.490   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    8   11                                                       
CONECT    8    7   12                                                       
CONECT    9    5   13                                                       
CONECT   10    1    6   12                                                  
CONECT   11    2    7   14                                                  
CONECT   12    8   10   13                                                  
CONECT   13    3    4    9   12                                             
CONECT   14   11                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-ol, 9ci	HMDB

Chemical Formula

C₁₃H₂₂O

Average Mass

194.3132 Da

Monoisotopic Mass

194.16707 Da

IUPAC Name

(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-ol

Traditional Name

(3E)-4-(2,6,6-trimethylcyclohex-2-en-1-yl)but-3-en-2-ol

CAS Registry Number

Not Available

SMILES

CC(O)\C=C\C1C(C)=CCCC1(C)C

InChI Identifier

InChI=1S/C13H22O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,11-12,14H,5,9H2,1-4H3/b8-7+

InChI Key

PWDOJWCZWKWKSE-BQYQJAHWSA-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
Melissa officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic 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	4.1	ALOGPS
logP	3.09	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	16.91	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.09 m³·mol⁻¹	ChemAxon
Polarizability	23.93 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

HMDB0038731

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018141

KNApSAcK ID

Not Available

Chemspider ID

4516121

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5363817

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
LOTUS database [Link]

Showing NP-Card for α-ionol (NP0261240)

MOL for NP0261240 (α-ionol)

3D MOL for NP0261240 (α-ionol)

3D SDF for NP0261240 (α-ionol)

3D-SDF for NP0261240 (α-ionol)

PDB for NP0261240 (α-ionol)

3D PDB for NP0261240 (α-ionol)

SMILES for NP0261240 (α-ionol)

INCHI for NP0261240 (α-ionol)

Structure for NP0261240 (α-ionol)

3D Structure for NP0261240 (α-ionol)