Cannabis Compound Database: Showing Compound Card for (-)-Epiafzelechin (CDB005191)

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Record Information

Version

1.0

Created at

2020-04-17 19:18:28 UTC

Updated at

2020-11-18 16:39:29 UTC

CannabisDB ID

CDB005191

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

(-)-Epiafzelechin

Description

(-)-Epiafzelechin belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4. Thus, (-)-epiafzelechin is considered to be a flavonoid lipid molecule (-)-Epiafzelechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (-)-Epiafzelechin is found, on average, in the highest concentration within tea (-)-Epiafzelechin has also been detected, but not quantified in, fruits and kiwis. This could make (-)-epiafzelechin a potential biomarker for the consumption of these foods. A catechin derivative having (2R,3R)-configuration. (-)-Epiafzelechin is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R,3R)-Epiafzelechin	ChEBI
Epi-afzelechin	ChEBI
Epiafzelechin	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.27

Monoisotopic Molecular Weight

274.0841

IUPAC Name

(2R,3R)-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

epiafzelechin

CAS Registry Number

24808-04-6

SMILES

O[C@@H]1CC2=C(O[C@@H]1C1=CC=C(O)C=C1)C=C(O)C=C2O

InChI Identifier

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2/t13-,15-/m1/s1

InChI Key

RSYUFYQTACJFML-UKRRQHHQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:31028 )
Flavan 3-ols (C12128 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020036 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	240 - 243 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.29	ALOGPS
logP	2.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	27.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(-)-Epiafzelechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-1970000000-97a69c7a45c624cc5456	Spectrum
Predicted GC-MS	(-)-Epiafzelechin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-002b-3700890000-ad3a8c90f22f6dcef7bc	Spectrum
Predicted GC-MS	(-)-Epiafzelechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(-)-Epiafzelechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004r-0690000000-4da2a1e1b8ae2d109c32	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004r-0690000000-3dda57eb8519237ff1d3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-004r-0690000000-90138410b48eec3cdf8b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-197f43a10026114cf6e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0a59-0910000000-4f271083ff1af2b4a646	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0930000000-fd8af365cba78f21a442	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0490000000-d1cb482bc9fba5c1c77c	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-0931dca1f9eede095b91	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-000j-0910000000-62c438a216915a5cb1cc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900000000-f191f6a8bfb1fdd83316	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0490000000-102c0099b32eb6cf1c1b	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0920000000-16e90c91e06078017d08	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-4900000000-1aa083295b52d9560bf8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0190000000-3f6f215ea99c3e0e4777	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0079-0940000000-10a1d2bf91d220a561c9	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-3910000000-d6da6b34ec8094f8de55	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0190000000-481c391516faccc36069	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-05g0-0970000000-dcc4eab79179a249d464	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-009f-4940000000-776437a8382970f7d1c2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-5b1317024b148033f6f6	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-0970000000-43adfba1cc7d810c20a9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4r-2920000000-8465db94f8820d798074	2021-09-24	View Spectrum