MiMeDB: Showing metabocard for 3,4-dihydrocoumarin (MMDBc0054243)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:01:19 UTC

Update Date

2024-09-29 12:27:51 UTC

Metabolite ID

MMDBc0054243

Metabolite Identification

Common Name

3,4-dihydrocoumarin

Description

3,4-Dihydro-2H-1-benzopyran-2-one, also known as 3,4-dihydrocoumarin or 1,2-benzodihydropyrone, belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position. 3,4-Dihydro-2H-1-benzopyran-2-one exists in all living organisms, ranging from bacteria to humans. 3,4-Dihydro-2H-1-benzopyran-2-one is a sweet, almond, and cinnamon tasting compound. 3,4-Dihydro-2H-1-benzopyran-2-one has been detected, but not quantified, in several different foods, such as green vegetables, pulses, sour cherries, and tarragons. A chromanone that is the 3,4-dihydro derivative of coumarin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

Synonyms

Value	Source
1,2-Benzodihydropyrone	ChEBI
2-Hydroxydihydrocinnamic acid lactone	ChEBI
3,4-Dihydro-2H-chromen-2-one	ChEBI
Benzodihydropyrone	ChEBI
Dihydrocoumarin	ChEBI
Hydrocoumarin	ChEBI
Melilotic acid lactone	ChEBI
Melilotic lactone	ChEBI
Melilotin	ChEBI
Melilotol	ChEBI
O-Hydroxydihydrocinnamic acid lactone	ChEBI
O-Hydroxyhydrocinnamic acid delta-lactone	ChEBI
3,4-Dihydrocoumarin	Kegg
2-Hydroxydihydrocinnamate lactone	Generator
Melilotate lactone	Generator
O-Hydroxydihydrocinnamate lactone	Generator
O-Hydroxyhydrocinnamate delta-lactone	Generator
O-Hydroxyhydrocinnamate δ-lactone	Generator
O-Hydroxyhydrocinnamic acid δ-lactone	Generator
2-Hydroxyhydrocinnamic lactone	HMDB
3,4-dihydro-1-Benzopyran-2-one	HMDB
3,4-dihydro-Coumarin	HMDB
3,4-Dihydroxycoumarin	HMDB
dihydro-Benzopyranone	HMDB
FEMA 2381	HMDB
Hydrocinnamic acid, O-hydroxy-, delta-lactone	HMDB
Hydrocoumarin, 8ci	HMDB
Melilotin (coumarin)	HMDB
Melilotin??	HMDB
O-Hydroxyhydrocinnamic acid lactone	HMDB

Molecular Formula

C₉H₈O₂

Average Mass

148.1586

Monoisotopic Mass

148.0524295

IUPAC Name

3,4-dihydro-2H-1-benzopyran-2-one

Traditional Name

dihydrocoumarin

CAS Registry Number

Not Available

SMILES

O=C1CCC2=CC=CC=C2O1

InChI Identifier

InChI=1S/C9H8O2/c10-9-6-5-7-3-1-2-4-8(7)11-9/h1-4H,5-6H2

InChI Key

VMUXSMXIQBNMGZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3,4-dihydrocoumarins. These are 3,4-dihydrogenated coumarins. Coumarin is a bicyclic compound that are 1-benzopyran carrying an oxo group at the 2-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

3,4-dihydrocoumarins

Sub Class

Not Available

Direct Parent

3,4-dihydrocoumarins

Alternative Parents

Substituents

3,4-dihydrocoumarin
Chromane
Benzopyran
1-benzopyran
Benzenoid
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

chromanone (CHEBI:16151 )
an aromatic compound (DIHYDROCOUMARIN )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.25 g/L	ALOGPS
logP	1.66	ALOGPS
logP	1.89	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-7.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	40.46 m³·mol⁻¹	ChemAxon
Polarizability	15.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ffw-9500000000-19f4cacfc3593f445e42	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-3a0260eb973faa6f27df	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-02du-2900000000-0780738b649dc11f75a4	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0ffw-9500000000-19f4cacfc3593f445e42	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0002-0910000000-3a0260eb973faa6f27df	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-02du-2900000000-0780738b649dc11f75a4	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fka-2900000000-071c9c2781c319fe04bf	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0002-0900000000-4aa1a496f0327462d05e	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-bacf3cdab2c00f9d3a52	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0a4i-0900000000-c86ad9f3b77d06e78084	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-1a9803adbe959ab8c397	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0a4i-0900000000-c86ad9f3b77d06e78084	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-4aa1a496f0327462d05e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-014i-0900000000-e00f4063d413008ffe40	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-bacf3cdab2c00f9d3a52	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-1a2460bc4ea458349c97	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-0900000000-9cfc6b98409c1ab92b17	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pb9-8900000000-4d6bcd5ccd07a0beeb52	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-f2275d03bd7d08c74531	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0f6t-0900000000-bcc997cb9c43e840687c	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f6x-9600000000-5eebf3f0198d365245af	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-c273ad6f431d1239485b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0592-1900000000-c7524399be04f94a7e32	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9400000000-364ed3e27ac756fed7b1	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-a4c75ebd26f0ac23a7eb	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014j-1900000000-107b906f2798b3915190	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00vl-6900000000-6809bdcaa3f757b499af	2021-09-23	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-006w-8900000000-1c291ea2d1c34d7a5a68	2015-03-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)		2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		2015-03-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human subgingival plaque

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0036626

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

660

PDB ID

Not Available

ChEBI ID

16151

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 3,4-dihydrocoumarin (MMDBc0054243)

MOL for #<Metabolite:0x00007f4705211710>

3D MOL for #<Metabolite:0x00007f4705211710>

3D SDF for #<Metabolite:0x00007f4705211710>

3D-SDF for #<Metabolite:0x00007f4705211710>

PDB for #<Metabolite:0x00007f4705211710>

3D PDB for #<Metabolite:0x00007f4705211710>

SMILES for #<Metabolite:0x00007f4705211710>

INCHI for #<Metabolite:0x00007f4705211710>

Structure for #<Metabolite:0x00007f4705211710>

3D Structure for #<Metabolite:0x00007f4705211710>