Showing Compound Procyanidin C (FDB021688)

Record Information

Version

1.0

Creation date

2011-03-17 23:26:51 UTC

Update date

2019-11-26 03:20:43 UTC

Primary ID

FDB021688

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Procyanidin C

Description

Ent-epicatechin(4alpha->8)catechin, also known as procyanidin b, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. Ent-epicatechin(4alpha->8)catechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Ent-epicatechin(4alpha->8)catechin can be found in sago palm, which makes ent-epicatechin(4alpha->8)catechin a potential biomarker for the consumption of this food product.

CAS Number

35356-33-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
3,3',4',5,7-Pentahydroxyflavan(4->8)-3,3',4',5,7-pentahydroxyflavan	db_source
ent-Epicatechin(4a->8)catechin	Generator
ent-Epicatechin(4α->8)catechin	Generator
ent-Epicatechin-(4a->8)-catechin	Generator
ent-Epicatechin-(4alpha->8)-catechin	HMDB
ent-Epicatechin-(4α->8)-catechin	Generator
Leucocyanidin 1	db_source
Proanthocyanidin C	db_source
Procyanidin b	MeSH, HMDB
Procyanidin C	db_source

Showing 1 to 10 of 10 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.29	ALOGPS
logP	3.12	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.69	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	220.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	146.51 m³·mol⁻¹	ChemAxon
Polarizability	56.91 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	No	ChemAxon

Chemical Formula

C30H26O12

IUPAC name

2-(3,4-dihydroxyphenyl)-8-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

InChI Identifier

InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2

InChI Key

XFZJEEAOWLFHDH-UHFFFAOYSA-N

Isomeric SMILES

OC1CC2=C(O)C=C(O)C(C3C(O)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=CC=C(O)C(O)=C1

Average Molecular Weight

578.5202

Monoisotopic Molecular Weight

578.142426296

Classification

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin
Flavan-3-ol
Hydroxyflavonoid
3'-hydroxyflavonoid
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
Flavan
Chromane
1-benzopyran
Benzopyran
Catechol
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a small molecule (CPD-7631 )

Ontology

No ontology term

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	Poorly sol. hexane	DFC
Isoelectric point	Not Available
Mass Composition	C 62.28%; H 4.53%; O 33.19%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03mj-0510690000-115aeaaab9de9537434c	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00g0-9310123000-1b5f06694d5c5932b95d	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, "ent-Epicatechin(4alpha->8)catechin,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_1_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	ent-Epicatechin-(4alpha->8)-catechin, TMS_2_13, 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	splash10-004i-0110980000-0e13fd95dfea7e071b3e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0445930000-8d4ec7eb9ff49f33784d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-0491110000-39d8fdee57a1fac6e045	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0110980000-0e13fd95dfea7e071b3e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0445930000-8d4ec7eb9ff49f33784d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-0491110000-39d8fdee57a1fac6e045	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0110980000-0e13fd95dfea7e071b3e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0445930000-8d4ec7eb9ff49f33784d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-0491110000-39d8fdee57a1fac6e045	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0110980000-0e13fd95dfea7e071b3e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0445930000-8d4ec7eb9ff49f33784d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-0491110000-39d8fdee57a1fac6e045	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0110980000-0e13fd95dfea7e071b3e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0445930000-8d4ec7eb9ff49f33784d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-0491110000-39d8fdee57a1fac6e045	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0110980000-0e13fd95dfea7e071b3e	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0445930000-8d4ec7eb9ff49f33784d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-059f-0491110000-39d8fdee57a1fac6e045	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0100290000-ff355bf530effad0a098	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kdr-0920440000-ebc860da7304aac4e05b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0910000000-3a88752aba968bcdfc9c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0100290000-ff355bf530effad0a098	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0kdr-0920440000-ebc860da7304aac4e05b	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0910000000-3a88752aba968bcdfc9c	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0100290000-ff355bf530effad0a098	2015-04-25	View 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

HGT19-P:HGT19-P

EAFUS ID

Not Available

Dr. Duke ID

4,8"-BISCATECHIN

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

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 Procyanidin C (FDB021688)

Structure for FDB021688 (Procyanidin C)