NP-MRD: Showing NP-Card for 4-hydroxy-2H-chromen-2-one (NP0331897)

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Record Information

Version

1.0

Created at

2023-09-28 20:01:37 UTC

Updated at

2024-05-11 00:26:19 UTC

NP-MRD ID

NP0331897

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-hydroxy-2H-chromen-2-one

Description

4-Hydroxy-2H-chromen-2-one, also known as 4-coumarinol or 4-hydroxy-2H-1-benzopyran-2-one, belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton. 4-Hydroxy-2H-chromen-2-one is an extremely weak basic (essentially neutral) compound (based on its pKa). It was first documented in 2004 (PMID: 18007464). A hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group (PMID: 19757094).

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 23-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-AUG-19         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -0.770   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       5.335   1.540   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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7    9                                                       
CONECT    6    3    7    8                                                  
CONECT    7    5    6   10                                                  
CONECT    8    4    6   12                                                  
CONECT    9    5   11   12                                                  
CONECT   10    7                                                            
CONECT   11    9                                                            
CONECT   12    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Value	Source
4-Coumarinol	ChEBI
4-Hydroxy-2-chromenone	ChEBI
4-Hydroxy-2H-1-benzopyran-2-one	ChEBI
4-Hydroxy-2H-benzo[b]pyran-2-one	ChEBI
Benzotetronic acid	ChEBI
Benzotetronate	Generator
4-Hydroxycoumarin (old)	HMDB
4-OH Coumarin	HMDB
4-HYDROXY-2H-chromen-2-one	ChEBI

Chemical Formula

C₉H₆O₃

Average Mass

162.1440 Da

Monoisotopic Mass

162.03169 Da

IUPAC Name

4-hydroxy-2H-chromen-2-one

Traditional Name

4-hydroxy-coumarin

CAS Registry Number

Not Available

SMILES

OC1=CC(=O)OC2=CC=CC=C12

InChI Identifier

InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H

InChI Key

VXIXUWQIVKSKSA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2023-09-28	View Spectrum

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

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-09	View Spectrum

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
Benzopyran
1-benzopyran
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:40070 )

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	1.01	ALOGPS
logP	1.03	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.3	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	43.44 m³·mol⁻¹	ChemAxon
Polarizability	15.24 Å³	ChemAxon
Number of Rings	2	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

HMDB0137904

DrugBank ID

DB03410

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093015

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C20414

BioCyc ID

CPD-12111

BiGG ID

Not Available

Wikipedia Link

4-Hydroxycoumarin

METLIN ID

Not Available

PubChem Compound

54682930

PDB ID

Not Available

ChEBI ID

40070

Good Scents ID

Not Available

References

General References

Stoyanov EV, Ivanov IC: Convenient replacement of the hydroxy by an amino group in 4 hydroxycoumarin and 4-hydroxy-6-methyl-2-pyrone under microwave irradiation. Molecules. 2004 Jul 31;9(8):627-31. doi: 10.3390/90800627. [PubMed:18007464 ]
Liu B, Raeth T, Beuerle T, Beerhues L: A novel 4-hydroxycoumarin biosynthetic pathway. Plant Mol Biol. 2010 Jan;72(1-2):17-25. doi: 10.1007/s11103-009-9548-0. Epub 2009 Sep 15. [PubMed:19757094 ]

Showing NP-Card for 4-hydroxy-2H-chromen-2-one (NP0331897)

MOL for NP0331897 (4-hydroxy-2H-chromen-2-one)

3D MOL for NP0331897 (4-hydroxy-2H-chromen-2-one)

3D SDF for NP0331897 (4-hydroxy-2H-chromen-2-one)

3D-SDF for NP0331897 (4-hydroxy-2H-chromen-2-one)

PDB for NP0331897 (4-hydroxy-2H-chromen-2-one)

3D PDB for NP0331897 (4-hydroxy-2H-chromen-2-one)

SMILES for NP0331897 (4-hydroxy-2H-chromen-2-one)

INCHI for NP0331897 (4-hydroxy-2H-chromen-2-one)

Structure for NP0331897 (4-hydroxy-2H-chromen-2-one)

3D Structure for NP0331897 (4-hydroxy-2H-chromen-2-one)