Cannabis Compound Database: Showing Compound Card for Caffeic acid (CDB006367)

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Record Information

Version

1.0

Created at

2020-11-03 16:25:45 UTC

Updated at

2022-12-13 19:31:27 UTC

CannabisDB ID

CDB006367

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Caffeic acid

Description

Caffeic acid, also known as trans-caffeate or sodium caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. The trans-isomer of caffeic acid. Caffeic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Caffeic acid has been detected, but not quantified in, several different foods, such as dandelions, green beans, common grapes, common beans, and sweet cherries. This could make caffeic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
3,4-Dihydroxy-trans-cinnamate	ChEBI
3,4-Dihydroxycinnamic acid	ChEBI
trans-Caffeate	ChEBI
3,4-Dihydroxy-trans-cinnamic acid	Generator
3,4-Dihydroxycinnamate	Generator
Caffeate	Generator
Caffeic acid, monosodium salt	HMDB
Caffeic acid, (e)-isomer	HMDB
Sodium caffeate	HMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3,4-Dihydroxycinnamic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acid	HMDB
(e)-Caffeic acid	HMDB
3,4-Dihydroxybenzeneacrylic acid	HMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acid	HMDB
3-(3,4-Dihydroxyphenyl)propenoic acid	HMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzene	HMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzene	HMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzene	HMDB
DHCA	HMDB
trans-3,4-Dihydroxycinnamic acid	HMDB
Caffeic acid	HMDB
3',4'-Dihydroxycinnamic acid	HMDB
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid;	HMDB

Chemical Formula

HTl

Average Molecular Weight

205.39

Monoisotopic Molecular Weight

205.982253

IUPAC Name

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

Traditional Name

caffeic acid

CAS Registry Number

Not Available

SMILES

[TlH]

InChI Identifier

InChI=1S/Tl.H

InChI Key

YWUHBIFVNJARPY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Hydroxycinnamic acids

Alternative Parents

Substituents

Cinnamic acid
Coumaric acid or derivatives
Hydroxycinnamic acid
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

caffeic acid (CHEBI:16433 )
Caffeate derivatives (C01197 )

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	1.67	ALOGPS
logP	1.53	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	3.64	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	47.02 m³·mol⁻¹	ChemAxon
Polarizability	17.34 Å³	ChemAxon
Number of Rings	1	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	, 3 TMS, GC-MS Spectrum	splash10-014i-1593000000-b24e97b50ed1f50252f3	Spectrum
GC-MS	, non-derivatized, GC-MS Spectrum	splash10-001i-9800000000-bae43e98e22babcbf5a7	Spectrum
GC-MS	, non-derivatized, GC-MS Spectrum	splash10-000i-9600000000-6140146b8e32bda5e3c9	Spectrum
GC-MS	, non-derivatized, GC-MS Spectrum	splash10-014i-0593000000-16610dfa8ac4ac67a4c2	Spectrum
GC-MS	, non-derivatized, GC-MS Spectrum	splash10-014i-1593000000-b24e97b50ed1f50252f3	Spectrum
GC-MS	, non-derivatized, GC-MS Spectrum	splash10-014i-0592000000-1bb03bc99be6718d247e	Spectrum
Predicted GC-MS	, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-1900000000-6a963e50b910f05b6825	Spectrum
Predicted GC-MS	, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00e9-5039000000-d55c6a31e04536d33b58	Spectrum
Predicted GC-MS	, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-90ad608487db4c112469	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0900000000-dcc07d9a43defb5683a0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-762c7a39be8e2819bc51	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-4900000000-e716811ee5cf56acce9e	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-037f59c6ff1daadca2a0	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0019-6900000000-a67fe3c28be25c2fa72b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-0019-1900000000-62d755ec157c381054b3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0900000000-6c93facd0d3caabc67f1	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-001r-0900000000-7b2d4553b6a25b853d4b	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-3ed879b5217c5d703cd5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0900000000-bddc5a2872c93f7185ba	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-000i-9600000000-376ae5146fc0f93c9ff5	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-7d707e3512f8df7d6c53	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-000i-0900000000-c904417e68f103c0c963	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-03di-0900000000-f31bbdf32d6b72a381e7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-ad7b879926d9c809f9c8	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014s-1900000000-d3c79213f8f23833fadc	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-3adb4dbfdaeb614b61e6	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9000000000-8f7413c3605b29515931	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2900000000-467621cde3e4486ad6bf	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-014i-0900000000-7fdae010c3ffe7ab1156	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-000i-9000000000-a67e2178525a89f45da9	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-8407d64b83bf427de33f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03dr-0900000000-91200c128446226f6ecb	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-2ec4b8c30dbd96e11228	2021-09-20	View Spectrum

NMR

Not Available

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	0.002 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.00112 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.00138 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.000959 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.00119 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.00292 mg/g dry wt	David S. Wishart,...	details