NP-MRD: Showing NP-Card for (2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid (NP0210918)

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Record Information

Version

2.0

Created at

2022-09-05 08:57:35 UTC

Updated at

2022-09-05 08:57:35 UTC

NP-MRD ID

NP0210918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid

Description

Pratenol B belongs to the class of organic compounds known as 1-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 1-position. Pratenol B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Pratenol B has been detected, but not quantified in, herbs and spices and tea. (2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid is found in Trifolium pratense. This could make pratenol b a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    0.7519   -3.1873    0.5035 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9093   -2.7683    0.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9146   -3.6260    1.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -1.5036   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -0.5594   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472    0.6856   -0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4425    1.6194   -1.3355 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6109    0.8702   -1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859    1.4432    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6000    0.7900    1.1800 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9695    2.8267    0.4605 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1331   -0.4715   -0.0340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7110    0.3675   -0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1196    0.4135   -0.1791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9906    1.3348   -0.7470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3032    1.3363   -0.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7538    0.4375    0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0970    0.4685    1.0045 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8744   -0.4819    1.1798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5621   -0.4858    0.7758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6177   -1.3943    1.3055 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059   -0.9753    1.3337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7393   -4.6133    1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4495   -1.2907   -0.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7837    1.6723   -1.8189 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1603   -0.0188   -1.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7312    3.4363    0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4428    1.0744   -1.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6341    2.0217   -1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0429    2.0265   -0.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7131    1.1327    0.5965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029   -1.1901    1.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4329   -1.4583    1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3558    0.0673    1.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  6  1  0
  6  7  2  0
  6  5  1  0
  5  4  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5 12  1  0
 12 13  2  0
 13 14  1  0
 14 20  2  0
 20 21  1  0
 21 22  1  0
 20 19  1  0
 19 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 22 12  1  0
 15 14  1  0
 11 27  1  0
  8 25  1  0
  8 26  1  0
  4 24  1  0
  3 23  1  0
 13 28  1  0
 22 33  1  0
 22 34  1  0
 19 32  1  0
 18 31  1  0
 16 30  1  0
 15 29  1  0
M  END


  Mrv0541 05061312002D          

 22 23  0  0  0  0            999 V2000
    1.4289    0.0000    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
    2.8579    0.0000    0.0000 C   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
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    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
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   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
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  9  3  2  0  0  0  0
  9  7  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  5  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  2  0  0  0  0
 14  5  1  0  0  0  0
 15  6  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  2  0  0  0  0
 18 14  2  0  0  0  0
 19 14  1  0  0  0  0
 20 15  2  0  0  0  0
 21 15  1  0  0  0  0
 22  7  1  0  0  0  0
 22 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CC(=O)C(=C\C(O)=O)\C1=CC2=C(OC1)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O7/c16-10-2-1-8-3-9(7-22-13(8)4-10)11(5-14(18)19)12(17)6-15(20)21/h1-5,16H,6-7H2,(H,18,19)(H,20,21)/b11-5+

> <INCHI_KEY>
WKBLWDNPQQYILN-VZUCSPMQSA-N

> <FORMULA>
C15H12O7

> <MOLECULAR_WEIGHT>
304.2516

> <EXACT_MASS>
304.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
28.103654417122232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(7-hydroxy-2H-chromen-3-yl)-4-oxohex-2-enedioic acid

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.3401403689999998

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.7665570273047337

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9113380392748134

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890886448246194

> <JCHEM_POLAR_SURFACE_AREA>
121.13

> <JCHEM_REFRACTIVITY>
75.5124

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-3-(7-hydroxy-2H-chromen-3-yl)-4-oxohex-2-enedioic 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   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337   0.000   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      12.003  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1   10                                                       
CONECT    3    8    9                                                       
CONECT    4   10   13                                                       
CONECT    5   11   14                                                       
CONECT    6   12   15                                                       
CONECT    7    9   22                                                       
CONECT    8    1    3   13                                                  
CONECT    9    3    7   11                                                  
CONECT   10    2    4   16                                                  
CONECT   11    5    9   12                                                  
CONECT   12    6   11   17                                                  
CONECT   13    4    8   22                                                  
CONECT   14    5   18   19                                                  
CONECT   15    6   20   21                                                  
CONECT   16   10                                                            
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19   14                                                            
CONECT   20   15                                                            
CONECT   21   15                                                            
CONECT   22    7   13                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(2E)-3-(7-Hydroxy-2H-chromen-3-yl)-4-oxohex-2-enedioate	Generator

Chemical Formula

C₁₅H₁₂O₇

Average Mass

304.2516 Da

Monoisotopic Mass

304.05830 Da

IUPAC Name

(2E)-3-(7-hydroxy-2H-chromen-3-yl)-4-oxohex-2-enedioic acid

Traditional Name

(2E)-3-(7-hydroxy-2H-chromen-3-yl)-4-oxohex-2-enedioic acid

CAS Registry Number

Not Available

SMILES

OC(=O)CC(=O)C(=C\C(O)=O)\C1=CC2=C(OC1)C=C(O)C=C2

InChI Identifier

InChI=1S/C15H12O7/c16-10-2-1-8-3-9(7-22-13(8)4-10)11(5-14(18)19)12(17)6-15(20)21/h1-5,16H,6-7H2,(H,18,19)(H,20,21)/b11-5+

InChI Key

WKBLWDNPQQYILN-VZUCSPMQSA-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
Trifolium pratense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-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 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
Medium-chain keto acid
Alkyl aryl ether
Beta-keto acid
Heterocyclic fatty acid
Hydroxy fatty acid
1-hydroxy-2-unsubstituted benzenoid
B'-hydroxy-alpha,beta-unsaturated-ketone
Benzenoid
1,3-dicarbonyl compound
Unsaturated fatty acid
Fatty acyl
Beta-hydroxy ketone
Keto acid
Alpha-branched alpha,beta-unsaturated-ketone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated ketone
Acryloyl-group
Enone
Ketone
Oxacycle
Ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
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	1.45	ALOGPS
logP	1.34	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-4.9	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	5	ChemAxon
Refractivity	75.51 m³·mol⁻¹	ChemAxon
Polarizability	28.1 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

HMDB0040631

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020422

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752877

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid (NP0210918)

MOL for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

3D MOL for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

3D SDF for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

3D-SDF for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

PDB for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

3D PDB for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

SMILES for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

INCHI for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

Structure for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)

3D Structure for NP0210918 ((2e)-3-(7-hydroxy-2h-chromen-3-yl)-4-oxohex-2-enedioic acid)