NP-MRD: Showing NP-Card for 3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid (NP0303346)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 17:37:10 UTC

Updated at

2022-09-10 17:37:10 UTC

NP-MRD ID

NP0303346

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid

Description

3-[(3R)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]propanoic acid belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. 3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid is found in Epicoccum nigrum. Based on a literature review very few articles have been published on 3-[(3R)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]propanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -5.6399    0.5299    0.4415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4498    0.8560   -0.1794 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2052    0.3046    0.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001   -0.7084    0.8964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -1.2653    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7061   -0.7575    0.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    0.2796   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1592    0.8267   -0.7524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3767    1.8248   -1.6245 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2645    0.7698   -1.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1613    1.7064   -2.1521 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4838    0.1651   -1.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7068   -0.3569    0.2278 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0631   -0.8903    0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1501    0.0725    0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3216    0.4819   -1.1945 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7032    0.0163   -2.1549 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576    1.4812   -1.4668 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6255   -1.4002    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6148   -0.4620    0.8961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9453    1.3130    1.2005 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4472    0.5179   -0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8016   -1.1279    1.5017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -2.0756    1.8015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8823    2.3418   -2.2515 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4949    0.4660    0.9856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2246   -1.8461   -0.0780 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1527   -1.1402    1.5971 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1471   -0.2748    0.5848 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9952    1.0386    0.7807 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2264    1.2387   -1.2905 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7339   -1.6405    1.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7735   -2.2852   -0.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6 19  1  0
 19 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 18  1  0
 16 17  2  0
 13 12  1  0
 12 10  1  0
 10 11  2  0
 10  7  1  0
  7  8  2  0
  8  9  1  0
  8  3  1  0
  7  6  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
 19 32  1  0
 19 33  1  0
 13 26  1  1
 14 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 18 31  1  0
  9 25  1  0
M  END


  Mrv1652309102219372D          

 19 20  0  0  1  0            999 V2000
   -2.1434   -0.4125    0.0000 C   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 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
    0.0000   -1.6500    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 O   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
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    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
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   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   -1.6500    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 13 19  1  0  0  0  0
  6 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303346

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C[C@@H](CCC(O)=O)OC(=O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O6/c1-18-9-4-2-7-6-8(3-5-10(14)15)19-13(17)11(7)12(9)16/h2,4,8,16H,3,5-6H2,1H3,(H,14,15)/t8-/m1/s1

> <INCHI_KEY>
QGTCWNLOZPVXIG-MRVPVSSYSA-N

> <FORMULA>
C13H14O6

> <MOLECULAR_WEIGHT>
266.249

> <EXACT_MASS>
266.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
25.834380626869837

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(3R)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]propanoic acid

> <JCHEM_LOGP>
2.0687990186666663

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
10.204488967569464

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3700060593804455

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4327303528696556

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
65.04620000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3R)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   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  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8                                                            
CONECT   10    7   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   13    6                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
3-[(3R)-8-Hydroxy-7-methoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]propanoate	Generator

Chemical Formula

C₁₃H₁₄O₆

Average Mass

266.2490 Da

Monoisotopic Mass

266.07904 Da

IUPAC Name

3-[(3R)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-1H-2-benzopyran-3-yl]propanoic acid

Traditional Name

3-[(3R)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C[C@@H](CCC(O)=O)OC(=O)C2=C1O

InChI Identifier

InChI=1S/C13H14O6/c1-18-9-4-2-7-6-8(3-5-10(14)15)19-13(17)11(7)12(9)16/h2,4,8,16H,3,5-6H2,1H3,(H,14,15)/t8-/m1/s1

InChI Key

QGTCWNLOZPVXIG-MRVPVSSYSA-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
Epicoccum nigrum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

2-benzopyrans

Direct Parent

2-benzopyrans

Alternative Parents

Substituents

2-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Dicarboxylic acid or derivatives
Vinylogous acid
Lactone
Carboxylic acid ester
Oxacycle
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	2.07	ChemAxon
pKa (Strongest Acidic)	3.37	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.05 m³·mol⁻¹	ChemAxon
Polarizability	25.83 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

75590313

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

146683008

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid (NP0303346)

MOL for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

3D MOL for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

3D SDF for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

3D-SDF for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

PDB for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

3D PDB for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

SMILES for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

INCHI for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

Structure for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)

3D Structure for NP0303346 (3-[(3r)-8-hydroxy-7-methoxy-1-oxo-3,4-dihydro-2-benzopyran-3-yl]propanoic acid)