NP-MRD: Showing NP-Card for meconic acid (NP0193707)

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Record Information

Version

2.0

Created at

2022-09-04 11:14:33 UTC

Updated at

2022-09-04 11:14:33 UTC

NP-MRD ID

NP0193707

Secondary Accession Numbers

None

Natural Product Identification

Common Name

meconic acid

Description

Poppy acid, also known as meconic acid or opium acid, belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Poppy acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Meconic acid is a dicarboxylic acid. Meconic acid gives a red color with ferric chloride. These salts as well as meconic acid esters are called meconates. Meconic acid constitutes about 5% of opium and can be used as an analytical marker for the presence of opium. Meconic acid was first isolated by Friedrich Sertürner in 1805. Its structure contains two carboxylic acid groups (-COOH) and one keto group (O) attached to a pyran ring. meconic acid is found in Papaver somniferum. Meconic acid is colorless and is only slightly soluble in water but readily soluble in alcohol.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061307172D          

 14 14  0  0  0  0            999 V2000
    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
    1.4289    0.0000    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    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
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    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
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  3  1  0  0  0  0
  7  5  1  0  0  0  0
  8  2  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  3  1  0  0  0  0
 14  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0193707

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC(=O)C(O)=C(O1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H4O7/c8-2-1-3(6(10)11)14-5(4(2)9)7(12)13/h1,9H,(H,10,11)(H,12,13)

> <INCHI_KEY>
ZEGRKMXCOCRTCS-UHFFFAOYSA-N

> <FORMULA>
C7H4O7

> <MOLECULAR_WEIGHT>
200.1025

> <EXACT_MASS>
199.995702482

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
15.80718900350467

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
-0.4003917926666667

> <ALOGPS_LOGS>
-1.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.637411580736235

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.689774939113919

> <JCHEM_PKA_STRONGEST_BASIC>
-4.826971488306953

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
42.51350000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.07e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4-oxopyran-2,6-dicarboxylic acid

> <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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334  -2.310   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       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4    8                                                  
CONECT    3    1    6   14                                                  
CONECT    4    2    5    9                                                  
CONECT    5    4    7   14                                                  
CONECT    6    3   10   11                                                  
CONECT    7    5   12   13                                                  
CONECT    8    2                                                            
CONECT    9    4                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    3    5                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-4-oxopyran-2,6-dicarboxylate	HMDB
3-Hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid	HMDB
3-Hydroxy-4-pyrone-2,6-dicarboxylic acid	HMDB
Meconic acid	HMDB
Opium acid	HMDB
Poppy acid	KEGG
Meconate	Generator

Chemical Formula

C₇H₄O₇

Average Mass

200.1025 Da

Monoisotopic Mass

199.99570 Da

IUPAC Name

3-hydroxy-4-oxo-4H-pyran-2,6-dicarboxylic acid

Traditional Name

3-hydroxy-4-oxopyran-2,6-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=CC(=O)C(O)=C(O1)C(O)=O

InChI Identifier

InChI=1S/C7H4O7/c8-2-1-3(6(10)11)14-5(4(2)9)7(12)13/h1,9H,(H,10,11)(H,12,13)

InChI Key

ZEGRKMXCOCRTCS-UHFFFAOYSA-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
Papaver somniferum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Pyranone
Dicarboxylic acid or derivatives
Heteroaromatic compound
Vinylogous acid
Cyclic ketone
Oxacycle
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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	-0.2	ALOGPS
logP	-0.4	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	1.69	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	121.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.51 m³·mol⁻¹	ChemAxon
Polarizability	15.81 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033695

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011804

KNApSAcK ID

Not Available

Chemspider ID

10465112

KEGG Compound ID

C20209

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Meconic acid

METLIN ID

Not Available

PubChem Compound

10347

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for meconic acid (NP0193707)

MOL for NP0193707 (meconic acid)

3D MOL for NP0193707 (meconic acid)

3D SDF for NP0193707 (meconic acid)

3D-SDF for NP0193707 (meconic acid)

PDB for NP0193707 (meconic acid)

3D PDB for NP0193707 (meconic acid)

SMILES for NP0193707 (meconic acid)

INCHI for NP0193707 (meconic acid)

Structure for NP0193707 (meconic acid)

3D Structure for NP0193707 (meconic acid)