Cannabis Compound Database: Showing Compound Card for Rhamnose (CDB000366)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-19 00:33:10 UTC

Updated at

2020-11-18 16:35:06 UTC

CannabisDB ID

CDB000366

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Rhamnose

Description

Rhamnose (Rham) is a naturally occurring deoxy sugar that is structurally derived from mannose. It can be classified as either a methyl-pentose or a 6-deoxy-hexose. It is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moiety. Rhamnose occurs in nature in its L-form as L-rhamnose (6-deoxy-L-mannose). This is unusual, since most of the naturally occurring sugars are in D-form. Rhamnose exists in two anomeric forms, alpha-L-rhamnose and beta-L- Rhamnose. Rhamnose is often bound to other sugars in nature. It is a common glycone component of many glycosides (such as phenolic glycosides) from many plants. In particular, rhamnose can be isolated from a number of plants including Buckthorn (Rhamnus), poison sumac, and various plants in the genus Uncaria. Rhamnose is moderately sweet, having a sweetness rating of about 33% of sucrose. Sweetness is detected through the binding of sugars to the T1R3 and T1R2 proteins, to form a G-protein coupled receptor that is the sweetness receptor in mammals. In addition to being found in plants, rhamnose is also a component of the outer cell membrane (especially of the lipopolysaccharides) of certain gram-negative bacteria including Klebsiella and Pseudomonas ( Ref:DOI ) as well as certain strains of Mycobacteria. L-rhamnose is metabolized to L-lactaldehyde, which is a branching point in the metabolic pathway of L-fucose and L-rhamnose utilization. Rhamnose is also one of many sugars that are found in cannabis plants (PMID: 6991645 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
alpha-6-Deoxy-L-mannose	ChEBI
alpha-L-Mannomethylose	ChEBI
alpha-L-Rha	ChEBI
alpha-L-Rhamnose	ChEBI
alpha-L-Rhap	ChEBI
alpha-L-Rhamnopyranose	Kegg
a-6-Deoxy-L-mannose	Generator
Α-6-deoxy-L-mannose	Generator
a-L-Mannomethylose	Generator
Α-L-mannomethylose	Generator
a-L-Rha	Generator
Α-L-rha	Generator
a-L-Rhamnose	Generator
Α-L-rhamnose	Generator
a-L-Rhap	Generator
Α-L-rhap	Generator
a-L-Rhamnopyranose	Generator

Chemical Formula

C₆H₁₂O₅

Average Molecular Weight

164.16

Monoisotopic Molecular Weight

164.0685

IUPAC Name

(2R,3R,4R,5R,6S)-6-methyloxane-2,3,4,5-tetrol

Traditional Name

α-L-rhamnopyranose

CAS Registry Number

10030-85-0

SMILES

C[C@@H]1O[C@@H](O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3-,4+,5+,6+/m0/s1

InChI Key

SHZGCJCMOBCMKK-HGVZOGFYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

L-rhamnopyranose (CHEBI:27907 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	91 to 93 °C	Wikipedia
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-1.9	ChemAxon
logS	0.7	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3.6	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	0	ChemAxon
Refractivity	34.38 m³·mol⁻¹	ChemAxon
Polarizability	15.26 Å³	ChemAxon
Number of Rings	1	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
EI-MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
Predicted GC-MS	Rhamnose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-1900000000-73abedcfedce730de924	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-1900000000-5f2bd8fc908e0f2d17d8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4s-9000000000-4ae8072a5651434f44b4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3900000000-e7a20de995c932bdb5d1	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dj-6900000000-03f10dd2373a0985cc0e	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-1ef6b887ff1a4477de1f	2015-09-15	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001129

Chemspider ID

Not Available

KEGG Compound ID

C02476

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439710

PDB ID

Not Available

ChEBI ID

27907

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Showing Compound Card for Rhamnose (CDB000366)

Structure for CDB000366 (Rhamnose)