AFCDB: Herniarin (FDB000963)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:47 UTC

Update date

2020-09-17 15:34:38 UTC

Primary ID

FDB000963

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Herniarin

Description

7-Methoxycoumarin or Herniarin, also known as ayapanin is a methoxy derivative of coumarin or a methyl derivative of umbelliferone. It belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 7-Methoxycoumarin is a neutral, hydrophobic molecule that is not soluble in water. It exists as a white to pale yellow powder. It has a pleasant balsamic, sweet or tonka taste/odor. 7-Methoxycoumarin is used as a scent or aroma agent in perfumes, lotions, facial moisturizers, hand creams, hair conditioners, household aerosols, lip balms and baby oils. 7-Methoxycoumarin occurs naturally in many plants and foods and has been detected, but not quantified in, several different plants, such as barley, tarragons, roman camomiles, fruits, and wild celeries. This could make 7-methoxycoumarin a potential biomarker for the consumption of these foods.

CAS Number

531-59-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
logP	1.88	ALOGPS
logP	1.63	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	35.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.01 m³·mol⁻¹	ChemAxon
Polarizability	17.43 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H8O3

IUPAC name

7-methoxy-2H-chromen-2-one

InChI Identifier

InChI=1S/C10H8O3/c1-12-8-4-2-7-3-5-10(11)13-9(7)6-8/h2-6H,1H3

InChI Key

LIIALPBMIOVAHH-UHFFFAOYSA-N

Isomeric SMILES

COC1=CC2=C(C=CC(=O)O2)C=C1

Average Molecular Weight

176.171

Monoisotopic Molecular Weight

176.047344118

Classification

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:5679 )
coumarins (C09268 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Poaceae

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 68.18%; H 4.58%; O 27.25%	DFC
Melting Point	Mp 117-118°	DFC
Boiling Point	Not Available
Experimental Water Solubility	0.133 mg/mL	BEILSTEIN
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	320 (e 14125) (MeOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-004j-3900000000-17e44e05c8fe2491778a	2015-03-01	View Spectrum
GC-MS	Herniarin, non-derivatized, GC-MS Spectrum	splash10-005a-5900000000-a51cb4413d70fe3ecdcc	Spectrum
GC-MS	Herniarin, non-derivatized, GC-MS Spectrum	splash10-004i-2900000000-5b9073b915d724268702	Spectrum
GC-MS	Herniarin, non-derivatized, GC-MS Spectrum	splash10-005a-5900000000-a51cb4413d70fe3ecdcc	Spectrum
GC-MS	Herniarin, non-derivatized, GC-MS Spectrum	splash10-004i-2900000000-5b9073b915d724268702	Spectrum
Predicted GC-MS	Herniarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000t-0900000000-213046cadb13b2437780	Spectrum
Predicted GC-MS	Herniarin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00e9-0900000000-4a3dcfd5346e0e2a65ca	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00e9-0900000000-e8134a5ce939ed389110	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00e9-0900000000-e8134a5ce939ed389110	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00b9-2900000000-8975e7f06b2c1779fc87	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 12V, negative	splash10-03dl-5900000000-d235a93122ae0924491c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 15V, negative	splash10-03ec-7900000000-a0be9b4582f568077239	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-QFT 22V, negative	splash10-03ec-9800000000-fb88eaf46b524a010367	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-001i-4900000000-79f400e005b4b0abd220	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-000l-9800000000-defb1852c01d2e5c3873	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-0006-9600000000-0b4321e67197e681a6c6	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9600000000-8662befff7041bc3c019	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9600000000-c8338c49921cebe4c808	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-001i-5900000000-7d4b5b1155355c18e680	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-004i-9100000000-a780bc6bc930a176af92	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-2a59cdf525e794c8bdd7	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-1900000000-6233a6992d4f3e8c7c6a	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-0b88e2f92a1ca7f4b51c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-9886d3e9db07e94c9008	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fis-3900000000-e49193208460a6f4cf59	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-b25d33bd5abcda83159d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-bc4c58f50f3e417616c4	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0zgi-2900000000-6b0a0a442b520d5079b6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-00ffe2c25b8beb0eeaa0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-3ab745d21b37980c4361	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0059-7900000000-5a569237127af07c25c1	2021-09-23	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

5679

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB29758

CRC / DFC (Dictionary of Food Compounds) ID

BSX04-T:BNX60-Y

EAFUS ID

Not Available

Dr. Duke ID

HERNIARIN

BIGG ID

Not Available

KNApSAcK ID

C00002476

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

531-59-9

GoodScent ID

rw1031831

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
aldose reductase inhibitor	48550	An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).	DUKE
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti allergic	50857	A drug used to treat allergic reactions.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti spasmodic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti staphylococcic	33282	A substance that kills or slows the growth of bacteria.	DUKE
candidicide			DUKE
cholagogue			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hepatoprotective	62868	Any compound that is able to prevent damage to the liver.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE
photoactive			DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
balsamic	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tonka	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Herniarin (FDB000963)

Structure for FDB000963 (Herniarin)