Cannabis Compound Database: Showing Compound Card for Coniferin (CDB005041)

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Record Information

Version

1.0

Created at

2020-04-17 19:03:21 UTC

Updated at

2020-11-18 16:39:14 UTC

CannabisDB ID

CDB005041

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Coniferin

Description

Coniferin, also known as abietin or coniferoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. Coniferin is an extremely weak basic (essentially neutral) compound (based on its pKa). Coniferin exists in all living organisms, ranging from bacteria to humans. A monosaccharide derivative that is coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. Coniferin 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
4-O-(beta-D-Glucosyl)-trans-coniferol	ChEBI
Coniferyl alcohol beta-D-glucoside	ChEBI
4-O-(b-D-Glucosyl)-trans-coniferol	Generator
4-O-(Β-D-glucosyl)-trans-coniferol	Generator
Coniferyl alcohol b-D-glucoside	Generator
Coniferyl alcohol β-D-glucoside	Generator
4-(3-Hydroxyprop-1-en-1-yl)-2-methoxyphenyl beta-D-glucopyranoside	HMDB
4-(3-Hydroxyprop-1-en-1-yl)-2-methoxyphenyl beta-delta-glucopyranoside	HMDB
Abietin	HMDB
Coniferoside	HMDB
Coniferyl alcohol beta-delta-glucoside	HMDB
Coniferyl alcohol-4-O-beta-D-glucopyranoside	HMDB
(e)-Coniferin	HMDB
3-(4beta-D-Glucopyranosyloxy-3-methoxy)phenyl-(2E)-propenol	HMDB
3-(4beta-D-Glucopyranosyloxy-3-methoxy)phenyl-2E-propenol	HMDB
3-(4Β-D-glucopyranosyloxy-3-methoxy)phenyl-(2E)-propenol	HMDB
3-(4Β-D-glucopyranosyloxy-3-methoxy)phenyl-2E-propenol	HMDB
4-(3-Hydroxy-1-propen-1-yl)-2-methoxyphenyl beta-glucopyranoside	HMDB
4-(3-Hydroxy-1-propen-1-yl)-2-methoxyphenyl β-glucopyranoside	HMDB
4-Hydroxy-3-methoxy-1-(gamma-hydroxypropenyl)benzene-4-D-glucoside	HMDB
4-Hydroxy-3-methoxy-1-(γ-hydroxypropenyl)benzene-4-D-glucoside	HMDB
4-[(1E)-3-Hydroxy-1-propen-1-yl]-2-methoxyphenyl beta-D-glucopyranoside	HMDB
4-[(1E)-3-Hydroxy-1-propen-1-yl]-2-methoxyphenyl β-D-glucopyranoside	HMDB
Coniferyl alcohol 4-O-glucoside	HMDB
Coniferyl alcohol beta-glucoside	HMDB
Coniferyl alcohol β-glucoside	HMDB
Laricin	HMDB
trans-Coniferin	HMDB
4-(3-Hydroxy-1-propenyl)-2-methoxyphenyl-beta-D-glucopyranoside	HMDB
4-(3-Hydroxy-1-propenyl)-2-methoxyphenyl-β-D-glucopyranoside	HMDB
Coniferosid	HMDB
Coniferin	HMDB

Chemical Formula

C₁₆H₂₂O₈

Average Molecular Weight

342.34

Monoisotopic Molecular Weight

342.1315

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{4-[(1E)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}oxane-3,4,5-triol

Traditional Name

coniferin

CAS Registry Number

124151-33-3

SMILES

COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=CC(\C=C\CO)=C1

InChI Identifier

InChI=1S/C16H22O8/c1-22-11-7-9(3-2-6-17)4-5-10(11)23-16-15(21)14(20)13(19)12(8-18)24-16/h2-5,7,12-21H,6,8H2,1H3/b3-2+/t12-,13-,14+,15-,16-/m1/s1

InChI Key

SFLMUHDGSQZDOW-FAOXUISGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
O-glycosyl compound
Cinnamyl alcohol
Phenoxy compound
Anisole
Methoxybenzene
Styrene
Phenol ether
Alkyl aryl ether
Monocyclic benzene moiety
Monosaccharide
Benzenoid
Oxane
Secondary alcohol
Ether
Organoheterocyclic compound
Acetal
Oxacycle
Polyol
Hydrocarbon derivative
Alcohol
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

aromatic ether (CHEBI:16220 )
monosaccharide derivative (CHEBI:16220 )
cinnamyl alcohol beta-D-glucoside (CHEBI:16220 )
Coniferyl alcohol derivatives (C00761 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	186 °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	-0.36	ALOGPS
logP	-0.91	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	128.84 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	83.78 m³·mol⁻¹	ChemAxon
Polarizability	34.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Coniferin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0759-9556000000-d50730990c533e558e82	Spectrum
Predicted GC-MS	Coniferin, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-014i-2131039000-cd8f01087972e82351ed	Spectrum
Predicted GC-MS	Coniferin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-014i-0009000000-65a612073ce47017ce11	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03gl-0907000000-0d21f83e25774ba0717e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0901000000-2a7d23914a39f0770405	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03ei-2900000000-05b53e9f75d7579a04b5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0709000000-f36f1c9d16f3e389f3e6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03fr-0902000000-32a6d5855356df41635a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03fs-2900000000-69153800d95873c33228	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-0943000000-a485932aa39f39c0ae69	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08i0-4932000000-c748bb7e8d1848b4f2c0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000j-2902000000-7422d619262b29c3e0f1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002e-0429000000-a9e8c4c6fd1a9702c50a	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kb-0911000000-3d8ce1e2b4fc8441ffd5	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03el-2910000000-554d1e09d40aac758ead	2021-09-25	View Spectrum