ContaminantDB: Proanthocyanidin A2

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 02:26:11 UTC

Update Date

2016-11-09 01:19:12 UTC

Accession Number

CHEM031159

Identification

Common Name

Proanthocyanidin A2

Class

Small Molecule

Description

Isolated from cassia bark (Cinnamomum aromaticum). Proanthocyanidin A2 is found in many foods, some of which are herbs and spices, cinnamon, avocado, and lingonberry.

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

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

Synonyms

Value	Source
Epicatechin-(2beta->7,4beta->8)-epicatechin	ChEBI
Epicatechin-(2b->7,4b->8)-epicatechin	Generator
Epicatechin-(2β->7,4β->8)-epicatechin	Generator
(+)-Proanthocyanidin a2	HMDB
EC-(4b,8)(2b,7)-ec	HMDB
Proanthocyanidin a-2	HMDB
Procyanidin a2	HMDB
Procyanidin dimer a2	HMDB
Procyanidoepicatechin	HMDB
Procyanidol a2	HMDB

Chemical Formula

C₃₁H₂₆O₁₂

Average Molecular Mass

590.531 g/mol

Monoisotopic Mass

590.142 g/mol

CAS Registry Number

41743-41-3

IUPAC Name

(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

Traditional Name

(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0²,¹¹.0³,⁸.0¹⁵,²⁰]henicosa-2(11),3(8),9,15(20),16,18-hexaene-6,9,17,19,21-pentol

SMILES

CC1=C(O)C(O)=CC(=C1)[C@@]12OC3=CC(O)=CC(O)=C3[C@@H]([C@H]1O)C1=C3O[C@@H]([C@H](O)CC3=C(O)C=C1O2)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C31H26O12/c1-11-4-13(6-20(37)27(11)39)31-30(40)26(24-19(36)7-14(32)8-22(24)42-31)25-23(43-31)10-17(34)15-9-21(38)28(41-29(15)25)12-2-3-16(33)18(35)5-12/h2-8,10,21,26,28,30,32-40H,9H2,1H3/t21-,26-,28-,30-,31+/m1/s1

InChI Key

DWMJRBXZWVVPDB-UYVQOXPASA-N

Chemical Taxonomy

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

proanthocyanidin (CHEBI:28472 )
hydroxyflavan (CHEBI:28472 )
Condensed tannins (Proanthocyanidins) (C10237 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.13 g/L	ALOGPS
logP	2.43	ALOGPS
logP	3.59	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.66	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	209.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	144.2 m³·mol⁻¹	ChemAxon
Polarizability	55.55 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0502790000-304f891b1b3211f028e2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05d0-9501045000-a879ec29ba94548eeefc	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Proanthocyanidin A2,1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-056r-0310690000-54ea277863ce3855e4f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-056r-0600930000-0793c36e7b827dadce6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900010000-eb8f4971f0158e4f45e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0110290000-ced82e7f8aa80a1b71ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pk9-0910470000-77ee610d048e0f3bfd15	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-0910000000-d53675b4ba6a9383bc64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000090000-97b4f0ce6c2f2f87ffc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0000390000-a31ae9550ae47c29b14a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00di-0230960000-c4d953d28ea849c22545	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000090000-0dcabebc8b6917f57a62	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0010690000-044c8d9bc85848e48151	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-1900660000-e3c8e610d8a5925f9195	Spectrum