Showing Compound Lignans (FDB005955)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:55 UTC

Update date

2025-11-18 23:00:33 UTC

Primary ID

FDB005955

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Lignans

Description

Lignans, also known as neolignans, belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one). Lignans has been detected, but not quantified in, several different foods, such as wild rice (Zizania), annual wild rice (Zizania aquatica), wheats (Triticum), common wheats (Triticum aestivum), and amaranths (Amaranthus). This could make lignans a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Lignans.

CAS Number

477-47-4

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Neolignans	MeSH
Lignan	MeSH
Neolignan	MeSH
Picropodophyllotoxin	HMDB
Podophyllotoxin	HMDB
Lignans	MeSH
Picropodophyllin	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.37	ALOGPS
logP	1.62	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.02	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	92.68 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	103.9 m³·mol⁻¹	ChemAxon
Polarizability	41.66 Å³	ChemAxon
Number of Rings	5	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

C22H22O8

IUPAC name

(10R,11S,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0³,⁷.0¹¹,¹⁵]hexadeca-1,3(7),8-trien-12-one

InChI Identifier

InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13?,18-,19-,20+/m1/s1

InChI Key

YJGVMLPVUAXIQN-BCVBHCCTSA-N

Isomeric SMILES

COC1=CC(=CC(OC)=C1OC)[C@H]1[C@H]2C(COC2=O)[C@@H](O)C2=CC3=C(OCO3)C=C12

Average Molecular Weight

414.4053

Monoisotopic Molecular Weight

414.13146768

Classification

Description

Belongs to the class of organic compounds known as podophyllotoxins. These are tetralin lignans in which the benzene moiety of the tetralin skeleton is fused to a 1,3-dioxolane and the cyclohexane is fused to a butyrolactone (pyrrolidin-2-one).

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan lactones

Sub Class

Podophyllotoxins

Direct Parent

Podophyllotoxins

Alternative Parents

Substituents

Podophyllotoxin
1-aryltetralin lignan
Linear furanonaphthodioxole
Naphthofuran
Tetralin
Benzodioxole
Phenoxy compound
Phenol ether
Anisole
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Oxacycle
Carboxylic acid derivative
Acetal
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Lignans (C10871 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Pharmaceutical industry:

Household products:

Antimicrobial agent

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	228 oC
Boiling Point	Not Available
Experimental Water Solubility	0.1 mg/mL at 25 oC	MERCK INDEX (1996)
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	Lignans, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-005j-0109000000-14f78dbe46f8312a8fb5	Spectrum
Predicted GC-MS	Lignans, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0kmi-1003900000-d43e5f990afbda30580d	Spectrum
Predicted GC-MS	Lignans, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Lignans, non-derivatized, 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	splash10-00kb-0009500000-4616d49ee91153709c32	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-0029100000-07a109dcecbceb611534	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gc0-0029000000-866502321774872dbd1f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0003900000-0a5bb4d2c68362569d3c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-02ta-0009200000-dc7b8f1ae65bdd58832d	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014j-1039000000-d11a736e9337d8575e1e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0020900000-1608d78c8539edf24423	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0043900000-e81bc57018acf33199a4	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-02vi-0039000000-552005d9b6b201ff3563	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0100900000-ec8194ed366395157a1b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-0009100000-bcb75b5aa88155a81414	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-2019100000-98fbf20ab2f57af37164	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

391314

ChEMBL ID

Not Available

KEGG Compound ID

C10871

Pubchem Compound ID

443013

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB01179

HMDB ID

HMDB31452

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

LIGNANS

BIGG ID

Not Available

KNApSAcK ID

C00033300

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
Allergenic	50904	A substance that triggers an immune response, causing allergic reactions. Its biological role is to stimulate the immune system, but it has no therapeutic applications. Key medical uses include diagnosing allergies and developing immunotherapies to desensitize patients to specific allergens, reducing the risk of severe reactions.	DUKE
Anti estrogenic	35222	An agent that blocks or reduces estrogen's effects, used to treat hormone-sensitive cancers, such as breast cancer, and manage conditions like endometriosis and uterine fibroids, by inhibiting estrogen's biological role in promoting cell growth.	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
Anti mycotic		An agent that destroys or prevents the growth of fungi, playing a crucial role in treating fungal infections. Therapeutically, it is used to manage conditions such as athlete's foot, ringworm, and candidiasis, and has key medical applications in dermatology and immunocompromised patient care.	DUKE
Anti-oxidant	22586	An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.	DUKE
Antitumor	35610	An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.	DUKE
Anti-viral	22587	An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.	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
Cardiovascular	38070	A system that transports blood, oxygen, and nutrients throughout the body, playing a crucial role in overall health. Therapeutically, cardiovascular agents manage conditions like hypertension, heart failure, and atherosclerosis, with key medical uses including regulating blood pressure, preventing blood clots, and improving cardiac function.	DUKE
Cathartic	75325	An agent that induces bowel movements, relieving constipation by stimulating intestinal motility. Its biological role is to increase water and electrolyte secretion in the gut. Therapeutically, cathartics are used to treat constipation, prepare the bowel for surgery or exams, and manage opioid-induced constipation. Key medical uses include laxative therapy and colonoscopy preparation.	DUKE