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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:34 UTC

Update Date

2023-02-21 17:18:47 UTC

HMDB ID

HMDB0029466

Secondary Accession Numbers

HMDB29466

Metabolite Identification

Common Name

Eugenitol

Description

Eugenitol belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. Based on a literature review very few articles have been published on Eugenitol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241214502D          

 15 16  0  0  0  0            999 V2000
    1.0721   -1.4429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121   -1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121   -2.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    1.4429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    2.2679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121    1.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8146   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8146   -1.4429    0.0000 O   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
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3 14  1  0  0  0  0
  5  6  2  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029466

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)C2=C(O1)C=C(O)C(C)=C2O

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O4/c1-5-3-8(13)10-9(15-5)4-7(12)6(2)11(10)14/h3-4,12,14H,1-2H3

> <INCHI_KEY>
HMAUJNAGOIPKDG-UHFFFAOYSA-N

> <FORMULA>
C11H10O4

> <MOLECULAR_WEIGHT>
206.1947

> <EXACT_MASS>
206.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.540303309967996

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2,6-dimethyl-4H-chromen-4-one

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
2.427844015333333

> <ALOGPS_LOGS>
-2.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.622012879225952

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.029920619451178

> <JCHEM_PKA_STRONGEST_BASIC>
-5.155785070524794

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
56.11020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.92e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2,6-dimethylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       2.001  -2.693   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.615  -1.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.769  -2.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.769  -4.233   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.001   1.924   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.615   2.693   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.615   4.233   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -0.769   1.924   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.769   0.384   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.615  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.001   0.384   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.387  -0.385   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.001  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.001  -1.924   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.387  -2.693   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4   14                                                  
CONECT    4    3                                                            
CONECT    5    6   11                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    2    9   11                                                  
CONECT   11    5   10   12                                                  
CONECT   12   11                                                            
CONECT   13    9   14                                                       
CONECT   14    3   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,7-Dihydroxy-2,6-dimethylchromone	HMDB

Chemical Formula

C₁₁H₁₀O₄

Average Molecular Weight

206.1947

Monoisotopic Molecular Weight

206.057908808

IUPAC Name

5,7-dihydroxy-2,6-dimethyl-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2,6-dimethylchromen-4-one

CAS Registry Number

491-48-5

SMILES

CC1=CC(=O)C2=C(O1)C=C(O)C(C)=C2O

InChI Identifier

InChI=1S/C11H10O4/c1-5-3-8(13)10-9(15-5)4-7(12)6(2)11(10)14/h3-4,12,14H,1-2H3

InChI Key

HMAUJNAGOIPKDG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029466)
Cytoplasm (HMDB: HMDB0029466)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029466)

Source

Endogenous

Endogenous (HMDB: HMDB0029466)

Plant

Plant (HMDB: HMDB0029466)

Exogenous

Food

Food (HMDB: HMDB0029466)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	290 - 292 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	834.7 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.92 g/L	ALOGPS
logP	1.89	ALOGPS
logP	2.43	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.03	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	56.11 m³·mol⁻¹	ChemAxon
Polarizability	20.54 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	147.457	30932474
DeepCCS	[M-H]-	145.062	30932474
DeepCCS	[M-2H]-	178.241	30932474
DeepCCS	[M+Na]+	153.507	30932474
AllCCS	[M+H]+	142.4	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	146.5	32859911
AllCCS	[M+Na]+	147.6	32859911
AllCCS	[M-H]-	143.2	32859911
AllCCS	[M+Na-2H]-	143.2	32859911
AllCCS	[M+HCOO]-	143.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eugenitol	CC1=CC(=O)C2=C(O1)C=C(O)C(C)=C2O	3142.6	Standard polar	33892256
Eugenitol	CC1=CC(=O)C2=C(O1)C=C(O)C(C)=C2O	2015.3	Standard non polar	33892256
Eugenitol	CC1=CC(=O)C2=C(O1)C=C(O)C(C)=C2O	2003.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eugenitol,1TMS,isomer #1	CC1=CC(=O)C2=C(O)C(C)=C(O[Si](C)(C)C)C=C2O1	2172.9	Semi standard non polar	33892256
Eugenitol,1TMS,isomer #2	CC1=CC(=O)C2=C(O[Si](C)(C)C)C(C)=C(O)C=C2O1	2157.4	Semi standard non polar	33892256
Eugenitol,2TMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C=C2O1	2265.2	Semi standard non polar	33892256
Eugenitol,1TBDMS,isomer #1	CC1=CC(=O)C2=C(O)C(C)=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2460.1	Semi standard non polar	33892256
Eugenitol,1TBDMS,isomer #2	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O)C=C2O1	2420.1	Semi standard non polar	33892256
Eugenitol,2TBDMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C=C2O1	2741.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eugenitol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0570-0920000000-93807f48e9b9d72995a3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eugenitol GC-MS (2 TMS) - 70eV, Positive	splash10-00g1-2394000000-581305fc50bbd4a45a45	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eugenitol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eugenitol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 10V, Positive-QTOF	splash10-0a4i-0290000000-ec54635de3ea1e032cf0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 20V, Positive-QTOF	splash10-0a4i-0790000000-60648fc48bd6cec81b1f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 40V, Positive-QTOF	splash10-00kk-3900000000-91d87efb2a43d1b730b3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 10V, Negative-QTOF	splash10-0a4i-0090000000-a689f6250bbe6b7fcd0e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 20V, Negative-QTOF	splash10-0a4i-0390000000-ddb98b07b4a52106cb5f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 40V, Negative-QTOF	splash10-00xr-5900000000-420c51a61ee6ce03a769	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 10V, Negative-QTOF	splash10-0a4i-0090000000-99c859898d8c3407680e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 20V, Negative-QTOF	splash10-0a4i-0190000000-07ea3a79b7f436475758	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 40V, Negative-QTOF	splash10-014i-9600000000-d7841e27eb91bf6912e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 10V, Positive-QTOF	splash10-0a4i-0090000000-d59b09fd60f8eef41793	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 20V, Positive-QTOF	splash10-0a4i-0390000000-4220e743b2a8f877ef5e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eugenitol 40V, Positive-QTOF	splash10-00dr-1900000000-f50e5739a28a91d775ac	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000587

KNApSAcK ID

C00050927

Chemspider ID

4214734

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5036604

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1809681

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Eugenitol (HMDB0029466)

MOL for HMDB0029466 (Eugenitol)

3D MOL for HMDB0029466 (Eugenitol)

3D SDF for HMDB0029466 (Eugenitol)

3D-SDF for HMDB0029466 (Eugenitol)

PDB for HMDB0029466 (Eugenitol)

3D PDB for HMDB0029466 (Eugenitol)

SMILES for HMDB0029466 (Eugenitol)

INCHI for HMDB0029466 (Eugenitol)

Structure for HMDB0029466 (Eugenitol)

3D Structure for HMDB0029466 (Eugenitol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra