ChemFOnt: Showing chemical card for Oenothein A (CFc000282312)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:33 UTC

Chemfont ID

CFc000282312

Molecule Identification

Common Name

Oenothein A

Definition

Oenothein a is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Oenothein a can be found in evening primrose, which makes oenothein a a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₁₀₂H₇₂O₆₆

Average Molecular Weight

2353.6235

Monoisotopic Molecular Weight

2352.227767356

IUPAC Name

3,4,5,13,21,22,23-heptahydroxy-8,18-dioxo-11-(3,4,5-trihydroxybenzoyloxy)-9,14,17-trioxatetracyclo[17.4.0.0²,⁷.0¹⁰,¹⁵]tricosa-1(19),2,4,6,20,22-hexaen-12-yl 2-{[4,5,6,19,20,21,29,30,31,37,46,47,50,51,58,59,63-heptadecahydroxy-8,16,34,42,54,60-hexaoxo-11,57-bis(3,4,5-trihydroxybenzoyloxy)-2,9,12,15,27,35,38,41,55,61-decaoxaundecacyclo[34.15.6.3¹³,²⁴.2²³,²⁶.1³,⁷.1¹⁰,¹⁴.0¹⁷,²².0²⁸,³³.0³⁹,⁵⁶.0⁴³,⁴⁸.0⁴⁹,⁵³]tetrahexaconta-1(51),3,5,7(64),17(22),18,20,23(59),24,26(58),28,30,32,43(48),44,46,49,52-octadecaen-45-yl]oxy}-3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

None

SMILES

OC1OC2COC(=O)C3=C(C(O)=C(O)C(O)=C3)C3=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)=C1OC1=CC2=C(C(O)=C1O)C1=C(O)C(O)=C3OC4=C(O)C(O)=C(O)C(=C4)C(=O)OC4C(O)C5OC(=O)C6=C(C(O)=C(O)C(O)=C6)C6=C(O)C(O)=C(OC7=C(O)C(O)=C(O)C=C7C(=O)OC7C(O)OC(COC2=O)C(OC(=O)C1=C3)C7OC(=O)C1=CC(O)=C(O)C(O)=C1)C=C6C(=O)OCC5OC4OC(=O)C1=CC(O)=C(O)C(O)=C1

InChI Identifier

InChI=1S/C102H72O66/c103-31-1-19(2-32(104)56(31)115)88(137)164-84-81-47(17-152-91(140)22-7-37(109)59(118)68(127)49(22)50-24(95(144)161-81)9-39(111)60(119)69(50)128)157-100(149)86(84)166-98(147)30-11-41(113)63(122)76(135)79(30)156-45-13-26-53(72(131)66(45)125)54-27-14-42(64(123)73(54)132)154-43-15-28(55(114)74(133)67(43)126)97(146)163-83-77(136)80-46(159-102(83)168-90(139)21-5-35(107)58(117)36(108)6-21)16-151-92(141)25-12-44(65(124)71(130)52(25)51-23(94(143)160-80)8-38(110)61(120)70(51)129)155-78-29(10-40(112)62(121)75(78)134)99(148)167-87-85(165-89(138)20-3-33(105)57(116)34(106)4-20)82(162-96(27)145)48(158-101(87)150)18-153-93(26)142/h1-15,46-48,77,80-87,100-136,149-150H,16-18H2

InChI Key

VIYPHOKMSVCJRH-UHFFFAOYSA-N

Chemical Taxonomy

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
Macrolide
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Diaryl ether
Benzoate ester
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Phenol ether
Phenoxy compound
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Oxane
Vinylogous acid
Lactone
Secondary alcohol
Carboxylic acid ester
Hemiacetal
Acetal
Polyol
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Ether
Hydrocarbon derivative
Organooxygen compound
Alcohol
Organic oxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302796)

Food

Herb and spice

Oilseed crop

Evening primrose (FooDB: FOOD00120)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Antineoplastic agent

Antitumor (HMDB: HMDB0302796)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.59 g/L	ALOGPS
logP	4.12	ALOGPS
logP	8.18	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	5.58	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	51	ChemAxon
Hydrogen Donor Count	36	ChemAxon
Polar Surface Area	1099.26 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	528.79 m³·mol⁻¹	ChemAxon
Polarizability	204.89 Å³	ChemAxon
Number of Rings	19	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0302796

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006296

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

157009963

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Oenothein A (CFc000282312)

MOL for CFc000282312 (Oenothein A)

3D MOL for CFc000282312 (Oenothein A)

3D SDF for CFc000282312 (Oenothein A)

3D-SDF for CFc000282312 (Oenothein A)

PDB for CFc000282312 (Oenothein A)

3D PDB for CFc000282312 (Oenothein A)

SMILES for CFc000282312 (Oenothein A)

INCHI for CFc000282312 (Oenothein A)

Structure for CFc000282312 (Oenothein A)

3D Structure for CFc000282312 (Oenothein A)