Showing Compound Theaflavin (FDB012511)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:13 UTC

Update date

2025-11-18 23:37:25 UTC

Primary ID

FDB012511

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Theaflavin

Description

Isotheaflavin belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Isotheaflavin has been detected, but not quantified in, several different foods, such as black tea, green tea, herbal tea, red tea, and teas (Camellia sinensis). This could make isotheaflavin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Isotheaflavin.

CAS Number

4670-05-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,8-Bis(3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl)-3,4,6-trihydroxy-5H-benzocyclohepten-5-one, 9CI	db_source
Theaflavine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.22 g/L	ALOGPS
logP	1.84	ALOGPS
logP	2.83	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.73	ChemAxon
pKa (Strongest Basic)	2.89	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	217.6 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.27 m³·mol⁻¹	ChemAxon
Polarizability	55.97 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C29H24O12

IUPAC name

3,4,6-trihydroxy-1,8-bis(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)-5H-benzo[7]annulen-5-one

InChI Identifier

InChI=1S/C29H24O12/c30-11-3-17(32)15-8-21(36)28(40-23(15)5-11)10-1-13-14(7-20(35)27(39)25(13)26(38)19(34)2-10)29-22(37)9-16-18(33)4-12(31)6-24(16)41-29/h1-7,21-22,28-33,35-37,39H,8-9H2,(H,34,38)

InChI Key

IPMYMEWFZKHGAX-UHFFFAOYSA-N

Isomeric SMILES

OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C2=C1C=C(C=C(O)C2=O)C1OC2=CC(O)=CC(O)=C2CC1O

Average Molecular Weight

564.4937

Monoisotopic Molecular Weight

564.126776232

Classification

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Benzopyran
Chromane
1-benzopyran
Tropolone
Tropone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Foods

Cocoa and cocoa products

Nuts and legumes:

Nuts

Fruits and vegetables:

Fruits:

Berries

Pomes:

Apple

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 61.70%; H 4.29%; O 34.01%	DFC
Melting Point	Mp 237-240° dec.	DFC
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	470 (e 3600) (EtOH) (Berdy)	DFC
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Isotheaflavin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0601-2104129000-5f64bce1a9b74a8794c4	Spectrum
Predicted GC-MS	Isotheaflavin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0012-0105090000-dbad9256eefd5ac73cef	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Isotheaflavin, TMS_2_15, 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	splash10-014j-0400190000-aba7cd070f494923cc4c	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901130000-19ff8617138242d42bbc	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0900110000-595c4e5339325a55cd10	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0100090000-b49c8ceebe73882cd9c5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ri-0612790000-af02cca8665ff5d8bce7	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1901020000-421f10b24f466f3fd655	2015-04-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

17216345

ChEMBL ID

CHEMBL1512440

KEGG Compound ID

Not Available

Pubchem Compound ID

22833651

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

133

DrugBank ID

Not Available

HMDB ID

HMDB05788

CRC / DFC (Dictionary of Food Compounds) ID

HHP83-R:HHP83-R

EAFUS ID

Not Available

Dr. Duke ID

THEAFLAVIN

BIGG ID

Not Available

KNApSAcK ID

C00009348

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

Theaflavin

Phenol-Explorer Metabolite ID

133

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
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 carcinogenic	35610	An agent that prevents or inhibits the formation of cancer, reducing tumor growth and proliferation. It plays a biological role in protecting cells from DNA damage and mutation. Therapeutically, it is used to prevent cancer development, with key medical applications in chemotherapy, radiation protection, and cancer prevention programs.	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
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
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Lipoxygenase inhibitor	35856	An agent that blocks the activity of lipoxygenase enzymes, reducing inflammation and oxidative stress. Therapeutically, it's used to manage conditions like asthma, atherosclerosis, and cancer, by inhibiting the production of pro-inflammatory leukotrienes. Key medical uses include treating respiratory and cardiovascular diseases.	DUKE
Mitogen	52290	A substance that induces cell division and proliferation, playing a key role in growth and development. Therapeutically, mitogens are used to stimulate tissue repair and regeneration. Medical applications include wound healing, tissue engineering, and cancer treatment, where mitogens can enhance chemotherapy efficacy or support hematopoiesis.	DUKE