NP-MRD: Showing NP-Card for 3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid (NP0011625)

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Record Information

Version

1.0

Created at

2021-01-05 21:15:18 UTC

Updated at

2021-07-15 17:09:28 UTC

NP-MRD ID

NP0011625

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid

Provided By

NPAtlas

Description

3-(4-Methoxy-2-oxo-2H-pyran-6-yl)propanoic 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. 3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid is found in Antrodia and Taiwanofungus camphoratus. It was first documented in 2013 (PMID: 23517145). Based on a literature review very few articles have been published on 3-(4-methoxy-2-oxo-2H-pyran-6-yl)propanoic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242116573D          

 24 24  0  0  0  0            999 V2000
   -3.7192   -1.4748   -0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5108   -0.1350    0.0562 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2566    0.4453    0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0787   -0.2620   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1451    0.3565   -0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3690   -0.4149   -0.3475 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6203    0.4192   -0.1943 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7697   -0.4548   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8075   -1.0644   -1.6046 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8156   -0.6188    0.3961 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2547    1.6218    0.2377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8182    2.3680    0.4985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7287    3.5847    0.7981 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0693    1.7719    0.4349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9425   -2.1637    0.1076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7851   -1.6004   -1.3628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7081   -1.7809    0.1946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1667   -1.3128   -0.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3053   -0.7902   -1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4115   -1.3127    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6457    0.7798    0.8403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5225    1.2410   -0.9562 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0719   -1.5692    0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9551    2.3667    0.6443 H   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14  3  2  0  0  0  0
  1 15  1  0  0  0  0
  1 16  1  0  0  0  0
  1 17  1  0  0  0  0
  4 18  1  0  0  0  0
  6 19  1  0  0  0  0
  6 20  1  0  0  0  0
  7 21  1  0  0  0  0
  7 22  1  0  0  0  0
 10 23  1  0  0  0  0
 14 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0011625

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C([H])([H])C([H])([H])C1=C([H])C(OC([H])([H])[H])=C([H])C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-13-7-4-6(2-3-8(10)11)14-9(12)5-7/h4-5H,2-3H2,1H3,(H,10,11)

> <INCHI_KEY>
ANMIXQYGZDPTLJ-UHFFFAOYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.174

> <EXACT_MASS>
198.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.035564010114292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-methoxy-2-oxo-2H-pyran-6-yl)propanoic acid

> <ALOGPS_LOGP>
1.10

> <JCHEM_LOGP>
0.3087583339999998

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.065865531102794

> <JCHEM_PKA_STRONGEST_BASIC>
-4.825263200433552

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
49.3485

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.95e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-methoxy-6-oxopyran-2-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.719  -1.475  -0.265  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.511  -0.135   0.056  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.257   0.445   0.115  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.079  -0.262  -0.143  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.145   0.357  -0.072  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.369  -0.415  -0.348  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.620   0.419  -0.194  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.770  -0.455  -0.507  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.808  -1.064  -1.605  0.00  0.00           O+0
HETATM   10  O   UNK     0       4.816  -0.619   0.396  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.255   1.622   0.238  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.818   2.368   0.499  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.729   3.585   0.798  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.069   1.772   0.435  0.00  0.00           C+0
HETATM   15  H   UNK     0      -2.942  -2.164   0.108  0.00  0.00           H+0
HETATM   16  H   UNK     0      -3.785  -1.600  -1.363  0.00  0.00           H+0
HETATM   17  H   UNK     0      -4.708  -1.781   0.195  0.00  0.00           H+0
HETATM   18  H   UNK     0      -1.167  -1.313  -0.404  0.00  0.00           H+0
HETATM   19  H   UNK     0       1.305  -0.790  -1.382  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.412  -1.313   0.331  0.00  0.00           H+0
HETATM   21  H   UNK     0       2.646   0.780   0.840  0.00  0.00           H+0
HETATM   22  H   UNK     0       2.523   1.241  -0.956  0.00  0.00           H+0
HETATM   23  H   UNK     0       5.072  -1.569   0.710  0.00  0.00           H+0
HETATM   24  H   UNK     0      -2.955   2.367   0.644  0.00  0.00           H+0
CONECT    1    2   15   16   17                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   18                                                  
CONECT    5    4    6   11                                                  
CONECT    6    5    7   19   20                                             
CONECT    7    6    8   21   22                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   23                                                       
CONECT   11    5   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    3   24                                                  
CONECT   15    1                                                            
CONECT   16    1                                                            
CONECT   17    1                                                            
CONECT   18    4                                                            
CONECT   19    6                                                            
CONECT   20    6                                                            
CONECT   21    7                                                            
CONECT   22    7                                                            
CONECT   23   10                                                            
CONECT   24   14                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
3-(4-Methoxy-2-oxo-2H-pyran-6-yl)propanoate	Generator

Chemical Formula

C₉H₁₀O₅

Average Mass

198.1740 Da

Monoisotopic Mass

198.05282 Da

IUPAC Name

3-(4-methoxy-2-oxo-2H-pyran-6-yl)propanoic acid

Traditional Name

3-(4-methoxy-6-oxopyran-2-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)OC(CCC(O)=O)=C1

InChI Identifier

InChI=1S/C9H10O5/c1-13-7-4-6(2-3-8(10)11)14-9(12)5-7/h4-5H,2-3H2,1H3,(H,10,11)

InChI Key

ANMIXQYGZDPTLJ-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Antrodia	NPAtlas	23517145
Taiwanofungus camphoratus	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

Alkyl aryl ether
Pyranone
Heteroaromatic compound
Vinylogous ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Oxacycle
Carbonyl group
Organic oxide
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
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	1.1	ALOGPS
logP	0.31	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.07	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	49.35 m³·mol⁻¹	ChemAxon
Polarizability	19.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA018805

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

29418907

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24123426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liaw CC, Chen YC, Huang GJ, Tsai YC, Chien SC, Wu JH, Wang SY, Chao LK, Sung PJ, Huang HC, Kuo YH: Anti-inflammatory lanostanoids and lactone derivatives from Antrodia camphorata. J Nat Prod. 2013 Apr 26;76(4):489-94. doi: 10.1021/np300443p. Epub 2013 Mar 21. [PubMed:23517145 ]

Showing NP-Card for 3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid (NP0011625)

MOL for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

3D MOL for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

3D SDF for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

3D-SDF for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

PDB for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

3D PDB for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

SMILES for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

INCHI for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

Structure for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)

3D Structure for NP0011625 (3-(4-methoxy-2-oxo-2H-pyran-6-yl)-propanoic acid)