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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:00 UTC

Update Date

2023-02-21 17:22:34 UTC

HMDB ID

HMDB0032652

Secondary Accession Numbers

HMDB32652

Metabolite Identification

Common Name

Meconine

Description

Meconine, also known as meconic lactone or mekonin, belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,. Based on a literature review very few articles have been published on Meconine.

Structure

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


  Mrv0541 05061306372D          

 14 15  0  0  0  0            999 V2000
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  3  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  2  0  0  0  0
  9  8  1  0  0  0  0
 10  8  1  0  0  0  0
 11 10  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  1  0  0  0  0
 14  5  1  0  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032652

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C2=C(COC2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O4/c1-12-7-4-3-6-5-14-10(11)8(6)9(7)13-2/h3-4H,5H2,1-2H3

> <INCHI_KEY>
ORFFGRQMMWVHIB-UHFFFAOYSA-N

> <FORMULA>
C10H10O4

> <MOLECULAR_WEIGHT>
194.184

> <EXACT_MASS>
194.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.8267418416937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
1.43

> <JCHEM_LOGP>
1.2126075500000002

> <ALOGPS_LOGS>
-2.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.215941430384984

> <JCHEM_PKA_STRONGEST_BASIC>
-4.628505541841565

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
49.56430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
meconin

> <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       5.198   5.923   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.744   5.553   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.173   2.843   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3    4    6                                                       
CONECT    4    3    7                                                       
CONECT    5    6   14                                                       
CONECT    6    3    5    8                                                  
CONECT    7    4    9   12                                                  
CONECT    8    6    9   10                                                  
CONECT    9    7    8   13                                                  
CONECT   10    8   11   14                                                  
CONECT   11   10                                                            
CONECT   12    1    7                                                       
CONECT   13    2    9                                                       
CONECT   14    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,7-Dimethoxy-1(3H)-isobenzofuranone	HMDB
6,7-Dimethoxy-2-benzofuran-1(3H)-one	HMDB
6,7-Dimethoxy-3H-isobenzofuran-1-one	HMDB
6,7-Dimethoxy-phthalide	HMDB
6,7-Dimethoxyphthalide	HMDB
Maconine	HMDB
Meconic lactone	HMDB
Meconin	HMDB
Mekonin	HMDB
Opianyl	HMDB

Chemical Formula

C₁₀H₁₀O₄

Average Molecular Weight

194.184

Monoisotopic Molecular Weight

194.057908808

IUPAC Name

6,7-dimethoxy-1,3-dihydro-2-benzofuran-1-one

Traditional Name

meconin

CAS Registry Number

569-31-3

SMILES

COC1=C(OC)C2=C(COC2=O)C=C1

InChI Identifier

InChI=1S/C10H10O4/c1-12-7-4-3-6-5-14-10(11)8(6)9(7)13-2/h3-4H,5H2,1-2H3

InChI Key

ORFFGRQMMWVHIB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phthalides. Phthalides are compounds containing a 3-hydrocarbylidene-2-benzofuran-1(3H)-one moiety,.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Isobenzofuranones

Direct Parent

Phthalides

Alternative Parents

Substituents

Phthalide
Anisole
Alkyl aryl ether
Benzenoid
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0032652)
Cytoplasm (HMDB: HMDB0032652)

Source

Endogenous

Endogenous (HMDB: HMDB0032652)

Exogenous

Food

Food (HMDB: HMDB0032652)

Exogenous (HMDB: HMDB0032652)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2.5 mg/mL at 25 °C	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.67 g/L	ALOGPS
logP	1.43	ALOGPS
logP	1.21	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.22	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	49.56 m³·mol⁻¹	ChemAxon
Polarizability	18.83 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]+	142.092	31661259
DarkChem	[M-H]-	140.041	31661259
DeepCCS	[M+H]+	143.194	30932474
DeepCCS	[M-H]-	140.836	30932474
DeepCCS	[M-2H]-	176.047	30932474
DeepCCS	[M+Na]+	151.255	30932474
AllCCS	[M+H]+	140.6	32859911
AllCCS	[M+H-H2O]+	136.3	32859911
AllCCS	[M+NH4]+	144.5	32859911
AllCCS	[M+Na]+	145.7	32859911
AllCCS	[M-H]-	141.0	32859911
AllCCS	[M+Na-2H]-	141.3	32859911
AllCCS	[M+HCOO]-	141.7	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.	5.33 minutes	32390414
Predicted by Siyang on May 30, 2022	12.3969 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.28 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1881.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	382.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	148.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	221.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	107.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	450.1 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	508.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	119.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1027.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	352.2 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	1186.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	318.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	464.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	447.7 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	88.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Meconine	COC1=C(OC)C2=C(COC2=O)C=C1	2724.9	Standard polar	33892256
Meconine	COC1=C(OC)C2=C(COC2=O)C=C1	1612.4	Standard non polar	33892256
Meconine	COC1=C(OC)C2=C(COC2=O)C=C1	1768.2	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 - Meconine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0wou-0900000000-2efb2c475068dfe351a4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Meconine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meconine LC-ESI-qTof , Positive-QTOF	splash10-0gx0-0900000000-e0cba3b2c81289d2d7c5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Meconine , positive-QTOF	splash10-0gx0-0900000000-e0cba3b2c81289d2d7c5	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 10V, Positive-QTOF	splash10-0002-0900000000-0933c36ce22f4e1425d1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 20V, Positive-QTOF	splash10-0002-0900000000-4440bc328c9bf6761063	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 40V, Positive-QTOF	splash10-00mk-0900000000-be04476ae7d39e7afbb8	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 10V, Negative-QTOF	splash10-0006-0900000000-1411ae31b9cb022b9dd6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 20V, Negative-QTOF	splash10-0006-0900000000-a9aa24b32e35c277ab22	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 40V, Negative-QTOF	splash10-004j-1900000000-919bff84e85809aa27c2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 10V, Negative-QTOF	splash10-0006-0900000000-3f1ce2e6c9a340ec1b90	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 20V, Negative-QTOF	splash10-0006-0900000000-ad2b54dfa94caa37f1e8	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 40V, Negative-QTOF	splash10-0002-0900000000-577ad8f468c8a697790a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 10V, Positive-QTOF	splash10-0002-0900000000-ba6daac79415d99e7ba0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 20V, Positive-QTOF	splash10-0002-0900000000-d33952d9c672ed32ecf7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Meconine 40V, Positive-QTOF	splash10-0a4r-4900000000-7c9ae29fe059caf789fd	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]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	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

FDB010602

KNApSAcK ID

C00051520

Chemspider ID

61717

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68437

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

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 Meconine (HMDB0032652)

MOL for HMDB0032652 (Meconine)

3D MOL for HMDB0032652 (Meconine)

3D SDF for HMDB0032652 (Meconine)

3D-SDF for HMDB0032652 (Meconine)

PDB for HMDB0032652 (Meconine)

3D PDB for HMDB0032652 (Meconine)

SMILES for HMDB0032652 (Meconine)

INCHI for HMDB0032652 (Meconine)

Structure for HMDB0032652 (Meconine)

3D Structure for HMDB0032652 (Meconine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra