Showing Compound Tellimagrandin I (FDB018804)

Record Information

Version

1.0

Creation date

2010-04-08 22:13:56 UTC

Update date

2020-02-24 19:11:09 UTC

Primary ID

FDB018804

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Tellimagrandin I

Description

3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. 3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate can be found in a number of food items such as cloves, rose hip, flaxseed, and guava, which makes 3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate a potential biomarker for the consumption of these food products.

CAS Number

30737-92-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3,4,5,13,21,22,23-Heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoic acid	Generator
2,3-Di-O-galloyl-4,6-(S)-hexahydroxydiphenoyl-D-glucopyranose	db_source
Colinin	db_source
Collinin?	db_source
Cornustannin 3	db_source
Tellimagrandin I	db_source

Predicted Properties

Property	Value	Source
Water Solubility	1.65 g/L	ALOGPS
logP	2.66	ALOGPS
logP	2.68	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	7.34	ChemAxon
pKa (Strongest Basic)	-6.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	13	ChemAxon
Polar Surface Area	377.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	178.06 m³·mol⁻¹	ChemAxon
Polarizability	70.91 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	Yes	ChemAxon

Chemical Formula

C34H26O22

IUPAC name

3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-12-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0^{2,7}.0^{10,15}]tricosa-1(23),2,4,6,19,21-hexaen-11-yl 3,4,5-trihydroxybenzoate

InChI Identifier

InChI=1S/C34H26O22/c35-12-1-8(2-13(36)21(12)41)30(47)55-28-27-18(53-34(51)29(28)56-31(48)9-3-14(37)22(42)15(38)4-9)7-52-32(49)10-5-16(39)23(43)25(45)19(10)20-11(33(50)54-27)6-17(40)24(44)26(20)46/h1-6,18,27-29,34-46,51H,7H2

InChI Key

YKDNTEQLKGYZHT-UHFFFAOYSA-N

Isomeric SMILES

OC1OC2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C2=CC(O)=C(O)C(O)=C2)C1OC(=O)C1=CC(O)=C(O)C(O)=C1

Average Molecular Weight

786.557

Monoisotopic Molecular Weight

786.091572516

Classification

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
Tetracarboxylic acid or derivatives
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Phenol
1-hydroxy-4-unsubstituted benzenoid
Monosaccharide
Monocyclic benzene moiety
Oxane
Benzenoid
Carboxylic acid ester
Hemiacetal
Lactone
Polyol
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Source:

Endogenous

Biological:

Plant

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 51.92%; H 3.33%; O 44.75%	DFC
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	[a]20D +121.4 (c, 1.3 in MeOH)	DFC
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	Tellimagrandin I, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00or-0707239300-3a18f4251ef339f995f8	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Tellimagrandin I, TMS_1_11, 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	splash10-0gbi-0417307900-8c46d072e20ac477307c	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0v00-0945205800-e150887f40737ad9a699	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-0894101000-2810808c4f2dace5e3fd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00kr-0201014900-eef4b81eaae2d1537cdd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-1911102300-5d517b1f7fc3cb78ee25	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0902000000-d4a8e80d38ff1e99d5a4	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kr-0000002900-b11f2fe628a29dec313f	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ftr-0500001900-b86f76634a3370f808a5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ufr-1912020400-ac14aa20e1129456d9aa	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0011000900-aad4281f66d32166d655	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-016r-0619104800-842b27294c9fc8313002	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1900100100-f2d248890a605cecbd7b	Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

LMS65-D:LMS68-G

EAFUS ID

Not Available

Dr. Duke ID

TELLIMAGRANDIN-I|COLININ

BIGG ID

Not Available

KNApSAcK ID

C00002938

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
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti herpetic	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti HIV	22587	A substance that destroys or inhibits replication of viruses.	DUKE
anti lipolytic			DUKE
anti viral	22587	A substance that destroys or inhibits replication of viruses.	DUKE
beta-adrenergic receptor blocker	37962	Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter.	DUKE
xanthine oxidase inhibitor	35634	An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).	DUKE