Cannabis Compound Database: Showing Compound Card for Catechin (CDB006365)

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Record Information

Version

1.0

Created at

2020-11-02 22:39:07 UTC

Updated at

2020-11-18 16:40:19 UTC

CannabisDB ID

CDB006365

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Catechin

Description

Catechin, also known as (2R,3S)-catechin or cianidanol, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Catechin is a bitter tasting compound. Catechin is found, on average, in the highest concentration within a few different foods, such as blackcurrants (Ribes nigrum), evergreen blackberries (Rubus laciniatus), and blackberries (Rubus) and in a lower concentration in mangos (Mangifera indica), nectarines (Prunus persica var. nucipersica), and cucumbers (Cucumis sativus). Catechin has also been detected, but not quantified in, several different foods, such as quinoas (Chenopodium quinoa), potatos (Solanum tuberosum), sacred lotus (Nelumbo nucifera), cloves (Syzygium aromaticum), and sweet marjorams (Origanum majorana). This could make catechin a potential biomarker for the consumption of these foods. Catechin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Catechin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol	ChEBI
(+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol	ChEBI
(+)-Catechol	ChEBI
(+)-Cyanidan-3-ol	ChEBI
(2R,3S)-(+)-Catechin	ChEBI
(2R,3S)-Catechin	ChEBI
(2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol	ChEBI
Catechuic acid	ChEBI
Cianidanol	ChEBI
Cyanidanol	ChEBI
D-Catechin	ChEBI
Catechuate	Generator
(+)-Catechin	HMDB, MeSH
(+)-Catechin hydrate	HMDB
(+)-Cyanidanol	HMDB, MeSH
(+/-)-catechin	HMDB
(+/-)-catechin hydrate	HMDB
3,3',4',5,7-Flavanpentol	HMDB, MeSH
Biocatechin	HMDB
Catechinate	HMDB
Catechinic acid	HMDB, MeSH
Catergen	HMDB, MeSH
Cianidanolum	HMDB
Cianidol	HMDB
D-(+)-Catechin	HMDB
trans3,3,4,5,7 Pentahydroxyflavane	HMDB
YK-85 light yellow powder 85	HMDB
Acid, catechinic	MeSH, HMDB
KB-53	MeSH, HMDB
Zyma	MeSH, HMDB
Cyanidanol 3	MeSH, HMDB
Cyanidanol-3	MeSH, HMDB
KB 53	MeSH, HMDB
Acid, catechuic	MeSH, HMDB
(+)-Cyanidanol-3	MeSH, HMDB
Epicatechin	MeSH, HMDB
Catechin	MeSH
(-)-Epicatechin	MeSH, HMDB
(+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol	PhytoBank
(+)-(2R:3S)-5,7,3’,4’-Tetrahydroxyflavan-3-ol	PhytoBank
(+)-3’,4’,5,7-Tetrahydroxy-2,3-trans-flavan-3-ol	PhytoBank
(+)-Cianidanol	PhytoBank
3-Cyanidanol, (+)-	PhytoBank
Cyanidol	PhytoBank
Dexcyanidanol	PhytoBank
trans-(+)-3,3',4',5,7-Flavanpentol	PhytoBank
trans-(+)-3,3’,4’,5,7-Flavanpentol	PhytoBank

Chemical Formula

C₁₅H₁₄O₆

Average Molecular Weight

290.2681

Monoisotopic Molecular Weight

290.07903818

IUPAC Name

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

Traditional Name

(+)-catechol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1

InChI Key

PFTAWBLQPZVEMU-DZGCQCFKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

catechin (CHEBI:15600 )
Flavans, Flavanols and Leucoanthocyanidins (C06562 )
Flavan 3-ols (C06562 )
Condensed tannins (Proanthocyanidins) (C06562 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020001 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	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	1.02	ALOGPS
logP	1.8	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74 m³·mol⁻¹	ChemAxon
Polarizability	27.89 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
GC-MS	Catechin, non-derivatized, GC-MS Spectrum	splash10-014i-0749000000-e5b0b7512526810c1758	Spectrum
GC-MS	Catechin, non-derivatized, GC-MS Spectrum	splash10-014i-0749000000-e5b0b7512526810c1758	Spectrum
GC-MS	Catechin, non-derivatized, GC-MS Spectrum	splash10-014i-0749000000-e5b0b7512526810c1758	Spectrum
GC-MS	Catechin, non-derivatized, GC-MS Spectrum	splash10-014i-0749000000-e5b0b7512526810c1758	Spectrum
Predicted GC-MS	Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-0940000000-3790a10ce8b93dcb9236	Spectrum
Predicted GC-MS	Catechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000i-3130069000-ca0968505fc89dd82640	Spectrum
Predicted GC-MS	Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-000i-0190000000-0b55363090666c3a1f0f	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0ab9-0900000000-5dfb75ce17e0aea0642b	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-003r-9000000000-ae956114187e6320ae3a	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0079-0900000000-dd93ef481c2fea84d4a2	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-052r-0980000000-97f9a54412368150d277	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0090010000-6ebf1de8cc1ea492a630	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-052k-0960000000-77945100b7a1f6311aea	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-052k-0960000000-77945100b7a1f6311aea	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 26V, Negative	splash10-05fr-0920000000-e829a07f24435afac743	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-000i-0090010000-6ebf1de8cc1ea492a630	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-052k-0960000000-77945100b7a1f6311aea	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-000i-0090000000-25414078e505f0193624	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 26V, Negative	splash10-05fr-0920000000-e829a07f24435afac743	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-000i-0910000000-a98df14e459446ae6ae2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00di-0090000000-142161e341ec3ee68a3a	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-0fga-0980000000-3406dfb006e610eb6fce	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-000i-0090000000-466d29d8274d012f2ea3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0pds-0970000000-2631ce85b21e59412694	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-05fr-1900000000-3424d3d2af180d7eabd3	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0590000000-aff1c3cc94786f87cacf	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0920000000-5e84c0d9207a0a018ab4	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05fr-4900000000-3e525d17e0b05647387a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0290000000-52e8123f5ed55bc47962	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0940000000-cfcd9b4e416f64a26916	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a6r-2910000000-be77474275eeee51824b	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.149 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.128 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.138 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.171 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.136 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.151 mg/g dry wt	David S. Wishart,...	details