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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:36 UTC

Update Date

2023-02-21 17:18:47 UTC

HMDB ID

HMDB0029472

Secondary Accession Numbers

HMDB29472

Metabolite Identification

Common Name

Isoeugenitol

Description

Isoeugenitol 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 Isoeugenitol.

Structure

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


  Mrv0541 05061304472D          

 15 16  0  0  0  0            999 V2000
    0.0000    2.4750    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
    3.5724    2.0625    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
    2.8579    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  5  3  2  0  0  0  0
  6  2  1  0  0  0  0
  7  4  2  0  0  0  0
  7  6  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15  5  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029472

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(=O)C2=C(O)C=C(O)C(C)=C2O1

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

> <INCHI_KEY>
XSSGQRFNGHRFBC-UHFFFAOYSA-N

> <FORMULA>
C11H10O4

> <MOLECULAR_WEIGHT>
206.1947

> <EXACT_MASS>
206.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.458223515066322

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2,8-dimethyl-4H-chromen-4-one

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.427844015333333

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.784780623788562

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.037735904089446

> <JCHEM_PKA_STRONGEST_BASIC>
-5.117659440063606

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
56.11020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.83e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-2,8-dimethylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

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       0.000   4.620   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   3.850   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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    6                                                            
CONECT    3    5    8                                                       
CONECT    4    7    9                                                       
CONECT    5    1    3   15                                                  
CONECT    6    2    7   11                                                  
CONECT    7    4    6   12                                                  
CONECT    8    3   10   13                                                  
CONECT    9    4   10   14                                                  
CONECT   10    8    9   11                                                  
CONECT   11    6   10   15                                                  
CONECT   12    7                                                            
CONECT   13    8                                                            
CONECT   14    9                                                            
CONECT   15    5   11                                                       
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-2,8-dimethylchromone	HMDB
5-Benzyl-5-(3-pyridinyl)-2,4-imidazolidinedione	HMDB
5-BENZYL-5-(3-pyridyl)hydantoin	HMDB

Chemical Formula

C₁₁H₁₀O₄

Average Molecular Weight

206.1947

Monoisotopic Molecular Weight

206.057908808

IUPAC Name

5,7-dihydroxy-2,8-dimethyl-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-2,8-dimethylchromen-4-one

CAS Registry Number

479-06-1

SMILES

CC1=CC(=O)C2=C(O)C=C(O)C(C)=C2O1

InChI Identifier

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

InChI Key

XSSGQRFNGHRFBC-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-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: HMDB0029472)
Cytoplasm (HMDB: HMDB0029472)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029472)

Source

Endogenous

Endogenous (HMDB: HMDB0029472)

Plant

Plant (HMDB: HMDB0029472)

Exogenous

Food

Food (HMDB: HMDB0029472)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029472)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	229 - 230 °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	1.83 g/L	ALOGPS
logP	1.9	ALOGPS
logP	2.43	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.04	ChemAxon
pKa (Strongest Basic)	-5.1	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	20.46 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]+	145.936	30932474
DeepCCS	[M-H]-	143.578	30932474
DeepCCS	[M-2H]-	177.354	30932474
DeepCCS	[M+Na]+	152.218	30932474
AllCCS	[M+H]+	142.0	32859911
AllCCS	[M+H-H2O]+	137.7	32859911
AllCCS	[M+NH4]+	146.1	32859911
AllCCS	[M+Na]+	147.2	32859911
AllCCS	[M-H]-	142.3	32859911
AllCCS	[M+Na-2H]-	142.2	32859911
AllCCS	[M+HCOO]-	142.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.51 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3205 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1670.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	355.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	215.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	293.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	495.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	736.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	912.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	413.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1479.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	474.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	204.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	117.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoeugenitol	CC1=CC(=O)C2=C(O)C=C(O)C(C)=C2O1	3069.7	Standard polar	33892256
Isoeugenitol	CC1=CC(=O)C2=C(O)C=C(O)C(C)=C2O1	2038.9	Standard non polar	33892256
Isoeugenitol	CC1=CC(=O)C2=C(O)C=C(O)C(C)=C2O1	1996.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoeugenitol,1TMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C)C=C(O)C(C)=C2O1	2164.1	Semi standard non polar	33892256
Isoeugenitol,1TMS,isomer #2	CC1=CC(=O)C2=C(O)C=C(O[Si](C)(C)C)C(C)=C2O1	2167.6	Semi standard non polar	33892256
Isoeugenitol,2TMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C(C)=C2O1	2240.7	Semi standard non polar	33892256
Isoeugenitol,1TBDMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O)C(C)=C2O1	2422.9	Semi standard non polar	33892256
Isoeugenitol,1TBDMS,isomer #2	CC1=CC(=O)C2=C(O)C=C(O[Si](C)(C)C(C)(C)C)C(C)=C2O1	2435.3	Semi standard non polar	33892256
Isoeugenitol,2TBDMS,isomer #1	CC1=CC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C(C)=C2O1	2699.1	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 - Isoeugenitol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bvr-0920000000-c94c28ce68641cfcac0f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoeugenitol GC-MS (2 TMS) - 70eV, Positive	splash10-009i-3395000000-cffe0baf646b92337de8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoeugenitol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoeugenitol 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 - Isoeugenitol 10V, Positive-QTOF	splash10-0a4i-0290000000-3efa17be4b9f7976f773	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 20V, Positive-QTOF	splash10-0a4i-0790000000-023b9a1454d85460125d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 40V, Positive-QTOF	splash10-00kk-4900000000-deca50087728c8703b98	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 10V, Negative-QTOF	splash10-0a4i-0090000000-0c314f7d313dfdc00798	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 20V, Negative-QTOF	splash10-0a4i-0390000000-012731caf09b35bd9c4e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 40V, Negative-QTOF	splash10-00dr-6900000000-2c1a74fbc1bc6b3acc61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 10V, Negative-QTOF	splash10-0a4i-0090000000-99c859898d8c3407680e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 20V, Negative-QTOF	splash10-0a4i-0190000000-807eb9dc076218a4ab36	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 40V, Negative-QTOF	splash10-01bc-5900000000-1a9d8005b7acef892f28	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 10V, Positive-QTOF	splash10-0a4i-0090000000-d59b09fd60f8eef41793	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 20V, Positive-QTOF	splash10-0a4i-0290000000-f7836032920b26173311	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoeugenitol 40V, Positive-QTOF	splash10-01p9-2900000000-fef5365e4092a5610fe2	2021-09-25	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

FDB000594

KNApSAcK ID

C00050927

Chemspider ID

4477104

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318562

PDB ID

Not Available

ChEBI ID

895319

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1809721

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 Isoeugenitol (HMDB0029472)

MOL for HMDB0029472 (Isoeugenitol)

3D MOL for HMDB0029472 (Isoeugenitol)

3D SDF for HMDB0029472 (Isoeugenitol)

3D-SDF for HMDB0029472 (Isoeugenitol)

PDB for HMDB0029472 (Isoeugenitol)

3D PDB for HMDB0029472 (Isoeugenitol)

SMILES for HMDB0029472 (Isoeugenitol)

INCHI for HMDB0029472 (Isoeugenitol)

Structure for HMDB0029472 (Isoeugenitol)

3D Structure for HMDB0029472 (Isoeugenitol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra