NP-MRD: Showing NP-Card for α-iron (NP0188203)

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Record Information

Version

2.0

Created at

2022-09-04 04:29:25 UTC

Updated at

2022-09-04 04:29:25 UTC

NP-MRD ID

NP0188203

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-iron

Description

Alpha-Irone, also known as 6-methyl-a-ionone or α-iron, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Alpha-Irone is an extremely weak basic (essentially neutral) compound (based on its pKa). Alpha-Irone is a berry, floral, and orris tasting compound. Outside of the human body,. α-iron is found in Iris sibirica. α-iron was first documented in 2007 (PMID: 18031907). A methyl ketone that is alpha-ionone in which a hydrogen at position 5 of the cyclohex-2-en-1-yl ring is substituted by a methyl group.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
    4.8470   -0.8744    0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6704   -0.4499   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7726   -0.2755   -1.7546 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104   -0.2466    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000    0.1335   -0.4243 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0074    0.3527    0.2370 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4643    1.7562    0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3031    2.7640   -0.7360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6613    2.0385    0.5654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182    0.9216    1.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3434   -0.3423    0.4577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6434   -1.4945    1.4056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800   -0.5544   -0.3089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6422   -1.9928   -0.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3163   -0.1362   -1.7560 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5590   -1.3205    1.2496 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5296   -0.0200    0.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4047   -1.6933   -0.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3248   -0.3970    1.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3705    0.2879   -1.4916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0354    0.1941    1.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3516    2.5833   -1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3455    2.8784   -0.3654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869    3.7424   -0.5827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0878    3.0269    0.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668    0.6668    2.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3864    1.1644    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2066   -0.2566   -0.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4319   -1.1392    2.1005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461   -1.6913    2.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903   -2.3929    0.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1508   -2.1080   -1.1079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5044   -2.5962   -0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3314   -2.3755    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2689   -0.6357   -2.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4861   -0.4687   -2.4002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5198    0.9509   -1.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 13  1  0
 13 14  1  0
 13 15  1  0
 13 11  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 11 28  1  6
 10 26  1  0
 10 27  1  0
  9 25  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  6 21  1  1
  5 20  1  0
  4 19  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv0541 05061308362D          

 15 15  0  0  0  0            999 V2000
   -0.7145   -0.4125    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
   -2.8579    0.8250    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
    0.1842    1.8695    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
    1.4289    0.0000    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
    0.0000    0.0000    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
   -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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  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  3  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0188203

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h6,8-9,11,13H,7H2,1-5H3/b9-8+

> <INCHI_KEY>
JZQOJFLIJNRDHK-CMDGGOBGSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.3239

> <EXACT_MASS>
206.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.21769969479232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(2,5,6,6-tetramethylcyclohex-2-en-1-yl)but-3-en-2-one

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
3.606300591333333

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.830479446571594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9062405241313165

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.6373

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-iron

> <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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   1.540   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       0.344   3.490   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       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   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  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   14                                                            
CONECT    5   14                                                            
CONECT    6    7   10                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10    1    6   13                                                  
CONECT   11    2    7   14                                                  
CONECT   12    3    8   15                                                  
CONECT   13    9   10   14                                                  
CONECT   14    4    5   11   13                                             
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
6-Methyl-alpha-ionone	ChEBI
alpha-Iron	ChEBI
Methyl alpha-ionone	ChEBI
Methyl-alpha-ionone	ChEBI
6-Methyl-a-ionone	Generator
6-Methyl-α-ionone	Generator
a-Iron	Generator
Α-iron	Generator
Methyl a-ionone	Generator
Methyl α-ionone	Generator
Methyl-a-ionone	Generator
Methyl-α-ionone	Generator
a-Irone	Generator
Α-irone	Generator
4-(2,5,6,6-Tetramethyl-2-cyclo-hexen-1-yl)-3-buten-2-one	HMDB
4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten-2-one	HMDB
4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten-2-one, 9ci	HMDB
4-(2,5,6,6-Tetramethylcyclohex-2-enyl)but-3-en-2-one	HMDB
6-Methyl ionone	HMDB
6-Methyl-alpha -ionone	HMDB
alpha -Irone	HMDB
alpha -Methyl-ionone	HMDB
alpha 6-Methyl--ionone	HMDB
alpha-Cyclocitrylidenebutanone	HMDB
alpha-Cyclocitrylidenemethyl ethyl ketone	HMDB
alpha-Inone, methyl- (6ci)	HMDB
cis-2,6-cis-(2(1),2(2))-alpha-Ionone	HMDB
FEMA 2597	HMDB
Ionone 6-methyl, alpha	HMDB
Irone	HMDB
Methyl-alpha -ionone	HMDB
Methyl-alpha-inone	HMDB

Chemical Formula

C₁₄H₂₂O

Average Mass

206.3239 Da

Monoisotopic Mass

206.16707 Da

IUPAC Name

(3E)-4-(2,5,6,6-tetramethylcyclohex-2-en-1-yl)but-3-en-2-one

Traditional Name

α-iron

CAS Registry Number

Not Available

SMILES

CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C

InChI Identifier

InChI=1S/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h6,8-9,11,13H,7H2,1-5H3/b9-8+

InChI Key

JZQOJFLIJNRDHK-CMDGGOBGSA-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
Iris sibirica	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
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

enone (CHEBI:10284 )
methyl ketone (CHEBI:10284 )

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	4.37	ALOGPS
logP	3.61	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.64 m³·mol⁻¹	ChemAxon
Polarizability	25.22 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

HMDB0035631

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Irone

METLIN ID

Not Available

PubChem Compound

5371002

PDB ID

Not Available

ChEBI ID

10284

Good Scents ID

Not Available

References

General References

Lalko J, Lapczynski A, McGinty D, Bhatia SP, Letizia CS, Api AM: Fragrance material review on alpha-irone. Food Chem Toxicol. 2007;45 Suppl 1:S272-5. doi: 10.1016/j.fct.2007.09.048. Epub 2007 Sep 14. [PubMed:18031907 ]
LOTUS database [Link]

Showing NP-Card for α-iron (NP0188203)

MOL for NP0188203 (α-iron)

3D MOL for NP0188203 (α-iron)

3D SDF for NP0188203 (α-iron)

3D-SDF for NP0188203 (α-iron)

PDB for NP0188203 (α-iron)

3D PDB for NP0188203 (α-iron)

SMILES for NP0188203 (α-iron)

INCHI for NP0188203 (α-iron)

Structure for NP0188203 (α-iron)

3D Structure for NP0188203 (α-iron)