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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:30:54 UTC

Update Date

2022-03-07 02:52:11 UTC

HMDB ID

HMDB0029518

Secondary Accession Numbers

HMDB29518

Metabolite Identification

Common Name

Liqcoumarin

Description

Liqcoumarin belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton. Based on a literature review a significant number of articles have been published on Liqcoumarin.

Structure

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

  Mrv0541 02241216332D          

 16 17  0  0  0  0            999 V2000
    0.7009   -1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4434   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4434   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7009   -2.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4434   -2.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4434    0.0821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416   -2.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0416    2.4747    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 16  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029518

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C1=C(O)C2=C(OC(=O)C=C2C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O4/c1-6-5-10(14)16-9-4-3-8(7(2)13)12(15)11(6)9/h3-5,15H,1-2H3

> <INCHI_KEY>
UMNMVZFOKSPTJN-UHFFFAOYSA-N

> <FORMULA>
C12H10O4

> <MOLECULAR_WEIGHT>
218.2054

> <EXACT_MASS>
218.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.560016272959665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-acetyl-5-hydroxy-4-methyl-2H-chromen-2-one

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
1.986836417333333

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.448166560830327

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.222569436211892

> <JCHEM_PKA_STRONGEST_BASIC>
-5.5455868357500995

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
58.2143

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-acetyl-5-hydroxy-4-methylchromen-2-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       1.308  -2.309   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.078  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.078  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.308   0.769   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.308   2.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.078   3.079   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.308   2.309   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.308   0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.694  -0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.694  -1.539   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.308  -2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.308  -3.849   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.694  -4.619   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.694   0.153   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.078  -4.619   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.078   4.619   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    2   10   12                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12                                                            
CONECT   14    4                                                            
CONECT   15   12                                                            
CONECT   16    6                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0029518
HETATM    1  C1  UNL     1      -4.059   0.184  -0.109  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.736   0.799  -0.413  1.00  0.00           C  
HETATM    3  O1  UNL     1      -2.749   1.901  -0.968  1.00  0.00           O  
HETATM    4  C3  UNL     1      -1.493   0.113  -0.061  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.581  -1.136   0.570  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.482  -1.867   0.945  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.791  -1.379   0.705  1.00  0.00           C  
HETATM    8  O2  UNL     1       1.852  -2.091   1.070  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.077  -1.671   0.864  1.00  0.00           C  
HETATM   10  O3  UNL     1       4.073  -2.386   1.230  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.286  -0.468   0.256  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.191   0.293  -0.133  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.372   1.613  -0.800  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.900  -0.150   0.084  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.230   0.584  -0.292  1.00  0.00           C  
HETATM   16  O4  UNL     1       0.003   1.778  -0.895  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.300   0.191   0.954  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.855   0.699  -0.678  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.041  -0.858  -0.534  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.602  -1.502   0.751  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.587  -2.832   1.433  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.263  -0.081   0.065  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.503   1.770  -0.806  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.050   1.633  -1.850  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.034   2.466  -0.176  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.680   2.398  -1.212  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5    5   15
CONECT    5    6   20
CONECT    6    7    7   21
CONECT    7    8   14
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   12   22
CONECT   12   13   14
CONECT   13   23   24   25
CONECT   14   15   15
CONECT   15   16
CONECT   16   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Acetyl-5-hydroxy-4-methylcoumarin	HMDB

Chemical Formula

C₁₂H₁₀O₄

Average Molecular Weight

218.2054

Monoisotopic Molecular Weight

218.057908808

IUPAC Name

6-acetyl-5-hydroxy-4-methyl-2H-chromen-2-one

Traditional Name

6-acetyl-5-hydroxy-4-methylchromen-2-one

CAS Registry Number

36695-19-9

SMILES

CC(=O)C1=C(O)C2=C(OC(=O)C=C2C)C=C1

InChI Identifier

InChI=1S/C12H10O4/c1-6-5-10(14)16-9-4-3-8(7(2)13)12(15)11(6)9/h3-5,15H,1-2H3

InChI Key

UMNMVZFOKSPTJN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

Hydroxycoumarins

Alternative Parents

Substituents

Hydroxycoumarin
Benzopyran
1-benzopyran
Acetophenone
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0029518)
Cytoplasm (HMDB: HMDB0029518)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029518)

Source

Endogenous

Endogenous (HMDB: HMDB0029518)

Plant

Plant (HMDB: HMDB0029518)

Exogenous

Food

Food (HMDB: HMDB0029518)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0029518)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 - 166 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2434 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	0.58 g/L	ALOGPS
logP	1.96	ALOGPS
logP	1.99	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	8.22	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	58.21 m³·mol⁻¹	ChemAxon
Polarizability	21.56 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
DarkChem	[M+H]+	149.094	31661259
DarkChem	[M-H]-	149.905	31661259
DeepCCS	[M+H]+	152.639	30932474
DeepCCS	[M-H]-	150.243	30932474
DeepCCS	[M-2H]-	183.324	30932474
DeepCCS	[M+Na]+	158.552	30932474
AllCCS	[M+H]+	145.8	32859911
AllCCS	[M+H-H2O]+	141.6	32859911
AllCCS	[M+NH4]+	149.7	32859911
AllCCS	[M+Na]+	150.8	32859911
AllCCS	[M-H]-	148.1	32859911
AllCCS	[M+Na-2H]-	148.0	32859911
AllCCS	[M+HCOO]-	148.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Liqcoumarin	CC(=O)C1=C(O)C2=C(OC(=O)C=C2C)C=C1	2846.1	Standard polar	33892256
Liqcoumarin	CC(=O)C1=C(O)C2=C(OC(=O)C=C2C)C=C1	2088.6	Standard non polar	33892256
Liqcoumarin	CC(=O)C1=C(O)C2=C(OC(=O)C=C2C)C=C1	2075.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Liqcoumarin,1TMS,isomer #1	CC(=O)C1=CC=C2OC(=O)C=C(C)C2=C1O[Si](C)(C)C	2241.4	Semi standard non polar	33892256
Liqcoumarin,1TBDMS,isomer #1	CC(=O)C1=CC=C2OC(=O)C=C(C)C2=C1O[Si](C)(C)C(C)(C)C	2478.4	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 - Liqcoumarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufu-2950000000-0adf4020491ff13d5098	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liqcoumarin GC-MS (1 TMS) - 70eV, Positive	splash10-00gj-3090000000-ce979716cf3ff168ac53	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Liqcoumarin 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 - Liqcoumarin 10V, Positive-QTOF	splash10-014i-0090000000-4ffe1759e8c180d39a8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 20V, Positive-QTOF	splash10-014i-0190000000-8603871f2b552935b362	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 40V, Positive-QTOF	splash10-0udi-5690000000-e4e278109c593b6ca294	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 10V, Negative-QTOF	splash10-014i-0190000000-2849d14cad9ea9301732	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 20V, Negative-QTOF	splash10-014i-0290000000-040448cc242d1634beb5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 40V, Negative-QTOF	splash10-0059-1920000000-4bdde9b16f7b4f2c076b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 10V, Positive-QTOF	splash10-014i-0090000000-55cf6f961546fa5b9f24	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 20V, Positive-QTOF	splash10-014i-0390000000-4c9a679b4ac6ee3e0d19	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 40V, Positive-QTOF	splash10-054x-1900000000-9f188c440ac214b36ed9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 10V, Negative-QTOF	splash10-014i-0090000000-66db57e616ee76e4cc3f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 20V, Negative-QTOF	splash10-016r-0790000000-19adf9c8bea4cd3dbeba	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Liqcoumarin 40V, Negative-QTOF	splash10-0feb-1910000000-5f3c6e484c98d2391b32	2021-09-25	Wishart 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

FDB000654

KNApSAcK ID

C00051290

Chemspider ID

9553881

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11378967

PDB ID

Not Available

ChEBI ID

174104

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1810151

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 Liqcoumarin (HMDB0029518)

MOL for HMDB0029518 (Liqcoumarin)

3D MOL for HMDB0029518 (Liqcoumarin)

3D SDF for HMDB0029518 (Liqcoumarin)

3D-SDF for HMDB0029518 (Liqcoumarin)

PDB for HMDB0029518 (Liqcoumarin)

3D PDB for HMDB0029518 (Liqcoumarin)

SMILES for HMDB0029518 (Liqcoumarin)

INCHI for HMDB0029518 (Liqcoumarin)

Structure for HMDB0029518 (Liqcoumarin)

3D Structure for HMDB0029518 (Liqcoumarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra