NP-MRD: Showing NP-Card for (2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid (NP0259745)

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Record Information

Version

2.0

Created at

2022-09-08 01:43:05 UTC

Updated at

2022-09-08 01:43:05 UTC

NP-MRD ID

NP0259745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid

Description

4-Hydroxy-3-(7-hydroxy-4-oxo-4H-1-benzopyran-3-yl)-2-hexenedioic acid belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety. (2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid is found in Aspergillus oryzae. Based on a literature review very few articles have been published on 4-Hydroxy-3-(7-hydroxy-4-oxo-4H-1-benzopyran-3-yl)-2-hexenedioic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.0677   -1.5955   -1.5253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9725   -2.1342   -1.6277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0529   -3.4635   -2.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460   -1.7489   -1.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2882   -0.5813   -0.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1200   -0.3882   -0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9911   -1.4708   -0.3359 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2711   -1.3203   -0.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8018   -0.1496    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1514   -0.0424    0.4453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6768    1.1909    0.6708 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0473    1.3206    0.9626 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9065    2.3251    0.6228 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5448    2.2160    0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    0.9688    0.1071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6344    0.8426   -0.1866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0002    1.9409   -0.2137 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3290    0.4018   -0.5052 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0508    1.5898   -1.1791 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835    0.6947    0.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8865   -0.5561    1.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9273   -1.3711    1.8719 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1227   -0.8364    2.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8438   -4.2464   -1.5819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7946   -2.4534   -1.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6628   -2.4667   -0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7791   -0.9075    0.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4677    2.2185    1.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    3.3043    0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9164    3.1051    0.2913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3265    0.0948   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0041    1.4040   -2.1637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8466    1.3140    1.4425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5422    1.2996    0.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9935   -0.4992    1.8581 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 18  1  0
 18 20  1  0
 20 21  1  0
 21 23  1  0
 21 22  2  0
 18  5  1  0
  5  4  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16  6  1  0
 15  9  1  0
 19 32  1  0
 18 31  1  6
 20 33  1  0
 20 34  1  0
 23 35  1  0
  4 25  1  0
  3 24  1  0
  7 26  1  0
 10 27  1  0
 12 28  1  0
 13 29  1  0
 14 30  1  0
M  END


  Mrv1652309082203432D          

 23 24  0  0  0  0            999 V2000
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    1.4289    0.0000    0.0000 O   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
    2.8579    0.0000    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
    4.2868   -0.0000    0.0000 O   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
    2.8579   -1.6500    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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 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
   -2.1434   -1.2375    0.0000 C   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
   -2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CC(O)=O)C(=C/C(O)=O)\C1=COC2=CC(O)=CC=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O8/c16-7-1-2-8-12(3-7)23-6-10(15(8)22)9(4-13(18)19)11(17)5-14(20)21/h1-4,6,11,16-17H,5H2,(H,18,19)(H,20,21)/b9-4-

> <INCHI_KEY>
JWGIPNWTSPSMIA-WTKPLQERSA-N

> <FORMULA>
C15H12O8

> <MOLECULAR_WEIGHT>
320.253

> <EXACT_MASS>
320.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
29.305259844246052

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-4-hydroxy-3-(7-hydroxy-4-oxo-4H-chromen-3-yl)hex-2-enedioic acid

> <JCHEM_LOGP>
0.06553801133333349

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
3.8545939863982204

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1821385696189233

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1551843812579436

> <JCHEM_POLAR_SURFACE_AREA>
141.36

> <JCHEM_REFRACTIVITY>
76.09769999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -4.620   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  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    9   16                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-3-(7-hydroxy-4-oxo-4H-1-benzopyran-3-yl)-2-hexenedioate	Generator

Chemical Formula

C₁₅H₁₂O₈

Average Mass

320.2530 Da

Monoisotopic Mass

320.05322 Da

IUPAC Name

(2Z)-4-hydroxy-3-(7-hydroxy-4-oxo-4H-chromen-3-yl)hex-2-enedioic acid

Traditional Name

(2Z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid

CAS Registry Number

Not Available

SMILES

OC(CC(O)=O)C(=C/C(O)=O)\C1=COC2=CC(O)=CC=C2C1=O

InChI Identifier

InChI=1S/C15H12O8/c16-7-1-2-8-12(3-7)23-6-10(15(8)22)9(4-13(18)19)11(17)5-14(20)21/h1-4,6,11,16-17H,5H2,(H,18,19)(H,20,21)/b9-4-

InChI Key

JWGIPNWTSPSMIA-WTKPLQERSA-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
Aspergillus oryzae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as chromones. Chromones are compounds containing a benzopyran-4-one moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Chromones

Alternative Parents

Substituents

Chromone
Medium-chain hydroxy acid
Medium-chain fatty acid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Heterocyclic fatty acid
Hydroxy fatty acid
Phenol
Pyranone
Dicarboxylic acid or derivatives
Hydroxy acid
Fatty acyl
Fatty acid
Pyran
Unsaturated fatty acid
Benzenoid
Heteroaromatic compound
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Carbonyl group
Organic oxide
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	0.066	ChemAxon
pKa (Strongest Acidic)	3.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	141.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	76.1 m³·mol⁻¹	ChemAxon
Polarizability	29.31 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

78435066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101481805

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid (NP0259745)

MOL for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

3D MOL for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

3D SDF for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

3D-SDF for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

PDB for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

3D PDB for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

SMILES for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

INCHI for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

Structure for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)

3D Structure for NP0259745 ((2z)-4-hydroxy-3-(7-hydroxy-4-oxochromen-3-yl)hex-2-enedioic acid)