Showing Compound Cirsimaritin (FDB001537)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:00 UTC

Update date

2025-11-18 22:31:56 UTC

Primary ID

FDB001537

Secondary Accession Numbers

FDB006912
FDB006991

Chemical Information

FooDB Name

Cirsimaritin

Description

Cirsimaritin, also known as 4',5-dihydroxy-6,7-dimethoxyflavone or scrophulein, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, cirsimaritin is considered to be a flavonoid lipid molecule. Cirsimaritin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cirsimaritin can be found in a number of food items such as italian oregano, lemon verbena, winter savory, and rosemary, which makes cirsimaritin a potential biomarker for the consumption of these food products.

CAS Number

6601-62-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
4',5-Dihydroxy-6,7-dimethoxyflavone	ChEBI
7-Methylcapillarisin	ChEBI
Scrophulein	ChEBI
Cirsimaritin	KEGG
4',5-Dihydroxy-6,7-dimethoxy-flavone	MeSH
Skrofulein	MeSH
Flavone, 4',5-dihydroxy-6,7-dimethoxy-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.042 g/L	ALOGPS
logP	3.21	ALOGPS
logP	2.69	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.58	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	83.86 m³·mol⁻¹	ChemAxon
Polarizability	31.91 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C17H14O6

IUPAC name

5-hydroxy-2-(4-hydroxyphenyl)-6,7-dimethoxy-4H-chromen-4-one

InChI Identifier

InChI=1S/C17H14O6/c1-21-14-8-13-15(16(20)17(14)22-2)11(19)7-12(23-13)9-3-5-10(18)6-4-9/h3-8,18,20H,1-2H3

InChI Key

ZIIAJIWLQUVGHB-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC)C(O)=C2C(=O)C=C(OC2=C1)C1=CC=C(O)C=C1

Average Molecular Weight

314.2895

Monoisotopic Molecular Weight

314.07903818

Classification

Description

Belongs to the class of organic compounds known as 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

O-methylated flavonoids

Direct Parent

7-O-methylated flavonoids

Alternative Parents

Substituents

6-methoxyflavonoid-skeleton
7-methoxyflavonoid-skeleton
4'-hydroxyflavonoid
5-hydroxyflavonoid
Flavone
Hydroxyflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dihydroxyflavone (CHEBI:81337 )
dimethoxyflavone (CHEBI:81337 )
Flavones and Flavonols (C17785 )
Flavones and Flavonols (LMPK12111163 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Cirsimaritin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001s-0591000000-e92c09c167cfa2ef2cfe	Spectrum
Predicted GC-MS	Cirsimaritin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsimaritin, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsimaritin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsimaritin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsimaritin, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsimaritin, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Cirsimaritin, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0zg0-0950000000-6064777e5cd3c59710e2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0059000000-f1dde0031b2a78c83a79	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0049000000-21e1793224fd178452b8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-2ba966f5b116ee95a95c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001j-0090000000-5b5f88dc83d372ecb683	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-02u0-1930000000-4cd8ace4861a5338df6c	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-ed71c0123432b938c36b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0029000000-362731b3dfab4a4f7f42	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0671-2690000000-dfb042072e2f781e183d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-fd9e5ad3f22beb3e5477	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0039000000-c22b90cc5de6c65d43a6	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2790000000-487278bfed0ce6d9c2b2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0009000000-2ba875095a8aafa31ef7	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0009000000-edb8a308e20d187ae6dd	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0291000000-ffacf3167c41ac9cf092	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0009000000-37aa871ad4ede2969f52	2021-10-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03ka-0097000000-14d65b8127a3c15885fb	2021-10-12	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

269

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

CIRSIMARITIN

BIGG ID

Not Available

KNApSAcK ID

C00003837

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

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 agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-mutagenic		An agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Cyclooxygenase-1 inhibitor	50630	An agent that blocks the activity of cyclooxygenase-1 (COX-1), reducing inflammation and pain. Therapeutically, it is used to manage conditions like arthritis, and as a nonsteroidal anti-inflammatory drug (NSAID) to relieve pain, fever, and inflammation, while minimizing gastrointestinal side effects.	DUKE
Cyclooxygenase-2 inhibitor	50629	An agent that blocks the activity of cyclooxygenase-2 (COX-2), reducing inflammation and pain. Therapeutically, it is used to manage conditions such as arthritis, menstrual cramps, and other inflammatory disorders, providing relief from symptoms with reduced gastrointestinal side effects compared to non-selective NSAIDs.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE