Showing Compound Citrusin A (FDB018763)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:55 UTC

Update date

2019-11-26 03:16:38 UTC

Primary ID

FDB018763

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Citrusin A

Description

Citrusin A belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. Citrusin A has been detected, but not quantified in, a few different foods, such as citrus, fruits, and lemons (Citrus limon). This could make citrusin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Citrusin A.

CAS Number

105279-09-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Predicted Properties

Property	Value	Source
Water Solubility	0.47 g/L	ALOGPS
logP	0.22	ALOGPS
logP	-0.77	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	187.76 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	133.24 m³·mol⁻¹	ChemAxon
Polarizability	54.95 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Chemical Formula

C26H34O12

IUPAC name

2-[4-(1,3-dihydroxy-2-{4-[(1Z)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}propyl)-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

InChI Identifier

InChI=1S/C26H34O12/c1-34-18-10-14(4-3-9-27)5-7-16(18)36-20(12-28)22(30)15-6-8-17(19(11-15)35-2)37-26-25(33)24(32)23(31)21(13-29)38-26/h3-8,10-11,20-33H,9,12-13H2,1-2H3/b4-3-

InChI Key

WHKMPWQXESJAPI-ARJAWSKDSA-N

Isomeric SMILES

COC1=C(OC(CO)C(O)C2=CC(OC)=C(OC3OC(CO)C(O)C(O)C3O)C=C2)C=CC(\C=C/CO)=C1

Average Molecular Weight

538.541

Monoisotopic Molecular Weight

538.205026552

Classification

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Cinnamyl alcohol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Polyol
Organic oxygen compound
Aromatic alcohol
Alcohol
Organooxygen compound
Hydrocarbon derivative
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 57.99%; H 6.36%; O 35.65%	DFC
Melting Point	Mp 108-109°	DFC
Optical Rotation	[a]20D -17.2 (c, 0.3 in MeOH)	DFC

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Citrusin A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0h90-4913160000-a53159e85a24267bf3b2	Spectrum
Predicted GC-MS	Citrusin A, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0i00-6904007000-d833764e55afc7f45738	Spectrum
Predicted GC-MS	Citrusin A, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_16, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Citrusin A, TMS_2_17, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05i9-0209070000-aad2c55eeb95ef762ae9	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0409010000-7feca6e8408cdd70d772	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gx0-1913000000-0bebdc70397f55491a66	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-1406190000-2438cc9a208d5664c64e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0914010000-7eabd1b2b4536b892ca1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fr-0900000000-7ff8f8300a808a809e2e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0zml-0104190000-28a534719a65978d2c2c	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-0409030000-5c11c5593eb44b1954f1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0907100000-4d9be0461b56abe9de23	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0319420000-a8acffb0481288460c51	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-2926340000-759961028322aae87c3f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052k-3916140000-e05025a1977bdb794e56	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

483806

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB39230

CRC / DFC (Dictionary of Food Compounds) ID

JYS61-J:LMQ03-Z

EAFUS ID

Not Available

Dr. Duke ID

CITRUSIN-A

BIGG ID

Not Available

KNApSAcK ID

Not Available

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

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).

Showing Compound Citrusin A (FDB018763)

Structure for FDB018763 (Citrusin A)