Cannabis Compound Database: Showing Compound Card for D-Fructose (CDB004855)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (11) Show 14 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:43:45 UTC

Updated at

2020-12-07 19:11:07 UTC

CannabisDB ID

CDB004855

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

D-Fructose

Description

D-Fructose, also known as levulosa or beta-levulose, belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond. D-Fructose is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Fructose exists in all living organisms, ranging from bacteria to humans. Within humans, D-fructose participates in a number of enzymatic reactions. In particular, D-fructose can be biosynthesized from sorbitol through the action of the enzyme sorbitol dehydrogenase. In addition, D-fructose can be biosynthesized from β-D-fructose 2-phosphate; which is mediated by the enzyme 14 kda phosphohistidine phosphatase. The UK’s Scientific Advisory Committee on Nutrition in 2015 disputed the claims of fructose causing metabolic disorders, stating that "there is insufficient evidence to demonstrate that fructose intake, at levels consumed in the normal UK diet, leads to adverse health outcomes independent of any effects related to its presence as a component of total and free sugars."The word "fructose" was coined in 1857 from the Latin for fructus (fruit) and the generic chemical suffix for sugars, -ose. In humans, D-fructose is involved in fructose intolerance, hereditary. Outside of the human body, D-Fructose has been detected, but not quantified in, several different foods, such as lentils, prairie turnips, purple lavers, elliott's blueberries, and mentha. This could make D-fructose a potential biomarker for the consumption of these foods. D-Fructose is a potentially toxic compound. D-Fructose 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
beta-D-Arabino-hexulose	ChEBI
beta-D-Fructose	ChEBI
beta-Fruit sugar	ChEBI
beta-Levulose	ChEBI
FRUCTOSE	ChEBI
b-D-Arabino-hexulose	Generator
Β-D-arabino-hexulose	Generator
b-D-Fructose	Generator
Β-D-fructose	Generator
b-Fruit sugar	Generator
Β-fruit sugar	Generator
b-Levulose	Generator
Β-levulose	Generator
beta-D-Fructofuranose	HMDB
beta-delta-Arabino-hexulose	HMDB
beta-delta-Fructofuranose	HMDB
beta-delta-Fructose	HMDB
D-(-)-Fructose	HMDB
delta-(-)-Fructose	HMDB
delta-Fructose	HMDB
FRU	HMDB
Fructon	HMDB
Levulose	HMDB
Braun brand OF fructose	HMDB
Fleboplast levulosa	HMDB
Fresenius kabi brand OF fructose	HMDB
Instituto farmacologico brand OF fructose	HMDB
Levulosa	HMDB
Levulosa ife	HMDB
Grifols brand OF fructose	HMDB
Levulosa baxter	HMDB
Levulosado braun	HMDB
Ern brand OF fructose	HMDB
Levulosa grifols	HMDB
Levulosa mein	HMDB
Levulosado vitulia	HMDB
Apir levulosa	HMDB
Baxter brand OF fructose	HMDB
Bieffe brand OF fructose	HMDB
Levulosa braun	HMDB
Levulosa ibys	HMDB
Levulosa, apir	HMDB
Levulosa, fleboplast	HMDB
Levulosado bieffe medit	HMDB
Plast apyr levulosa mein	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.16

Monoisotopic Molecular Weight

180.0634

IUPAC Name

(2R,3S,4S,5R)-2,5-bis(hydroxymethyl)oxolane-2,3,4-triol

Traditional Name

fructose

CAS Registry Number

53188-23-1

SMILES

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

InChI Identifier

InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6-/m1/s1

InChI Key

RFSUNEUAIZKAJO-ARQDHWQXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a C-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

C-glycosyl compounds

Alternative Parents

Substituents

C-glycosyl compound
Pentose monosaccharide
Monosaccharide
Tetrahydrofuran
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-fructofuranose (CHEBI:28645 )

Ontology

Hypertension

Metabolism and nutrition disorders:

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Biofluid and excreta:

Cell and elements:

Extracellular

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	119 - 122 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	778 mg/mL at 20 °C	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.4	ALOGPS
logP	-2.8	ChemAxon
logS	0.79	ALOGPS
pKa (Strongest Acidic)	10.28	ChemAxon
pKa (Strongest Basic)	-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	2	ChemAxon
Refractivity	36.36 m³·mol⁻¹	ChemAxon
Polarizability	16.26 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
Predicted GC-MS	D-Fructose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-076r-9600000000-f2c06850d0c3db9ec103	Spectrum
Predicted GC-MS	D-Fructose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fb9-5614950000-6ef14e948d063026f7ee	Spectrum
Predicted GC-MS	D-Fructose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_3_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	D-Fructose, TMS_3_6, 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, Positive (Annotated)	splash10-0002-0900000000-2ce9036c30158be73d60	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00ri-9600000000-a826b29724713036f579	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-007a-9200000000-7621d8d96132cc999f4c	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, negative	splash10-000i-9000000000-f40ae4502b6a2e3ac882	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, negative	splash10-00di-9000000000-a6de82c4270a43535ef4	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 40V, negative	splash10-00di-9000000000-f9fa2c446096028a62b8	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-000i-9000000000-f40ae4502b6a2e3ac882	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-00di-9000000000-a6de82c4270a43535ef4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-00di-9000000000-f9fa2c446096028a62b8	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-2afc98a319bf6041adf0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-3900000000-1dd0cdea93f529e6ccb2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9100000000-d0f08ad6c9dee008067a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-74b62c8ea3678afcff8a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ta-1900000000-5a0f3f01ddf8c11c6370	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-93c2b00aa44481aa8630	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-056r-9800000000-b033c19e1db6b17bf7cf	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9500000000-01306ef5e3c5a271dfb2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-4e87bfc49b1664133053	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-6aefe19f3e63c1b3fbef	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03gm-9500000000-d2f178dbda765758ef3d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0btd-9000000000-62631cc26542b523e7d7	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Starch and Sucrose Metabolism
Galactose Metabolism
Fructose and Mannose Degradation
Amino Sugar Metabolism
Sialuria or French Type Sialuria		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Hexokinase-3	HK3	5q35.2	P52790	details
Hexokinase-2	HK2	2p13	P52789	details
Hexokinase-1	HK1	10q22	P19367	details
Sucrase-isomaltase, intestinal	SI		P14410	details
Sorbitol dehydrogenase	SORD	15q15.3	Q00796	details
Ketohexokinase	KHK	2p23.3	P50053	details
Lysosomal alpha-glucosidase	GAA		P10253	details
Maltase-glucoamylase, intestinal	MGAM		O43451	details
Neutral alpha-glucosidase C	GANC		Q8TET4	details
14 kDa phosphohistidine phosphatase	PHPT1		Q9NRX4	details
Putative hexokinase HKDC1	HKDC1	10q22.1	Q2TB90	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sorbitol dehydrogenase	SORD	15q15.3	Q00796	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
14 kDa phosphohistidine phosphatase	PHPT1		Q9NRX4	details
Myotubularin-related protein 2	MTMR2		Q13614	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000660

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

General References

Not Available

Only showing the first 10 proteins. There are 14 proteins in total.

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Enzymes

Enzyme Details

1. Hexokinase-3

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK3
Uniprot ID:: P52790
Molecular weight:: 99024.56

Enzyme Details

2. Hexokinase-2

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK2
Uniprot ID:: P52789
Molecular weight:: 102379.06

Enzyme Details

3. Hexokinase-1

General function:: Involved in ATP binding
Specific function:: Not Available
Gene Name:: HK1
Uniprot ID:: P19367
Molecular weight:: 102485.1

Enzyme Details

4. Sucrase-isomaltase, intestinal

General function:: Involved in catalytic activity
Specific function:: Plays an important role in the final stage of carbohydrate digestion. Isomaltase activity is specific for both alpha-1,4- and alpha-1,6-oligosaccharides.
Gene Name:: SI
Uniprot ID:: P14410
Molecular weight:: Not Available

Enzyme Details

5. Sorbitol dehydrogenase

General function:: Involved in zinc ion binding
Specific function:: Converts sorbitol to fructose. Part of the polyol pathway that plays an important role in sperm physiology. May play a role in the sperm motility by providing an energetic source for sperm (By similarity).
Gene Name:: SORD
Uniprot ID:: Q00796
Molecular weight:: 38324.25

Enzyme Details

6. Ketohexokinase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: KHK
Uniprot ID:: P50053
Molecular weight:: 32730.055

Enzyme Details

7. Lysosomal alpha-glucosidase

General function:: Involved in catalytic activity
Specific function:: Essential for the degradation of glygogen to glucose in lysosomes.
Gene Name:: GAA
Uniprot ID:: P10253
Molecular weight:: Not Available

Enzyme Details

8. Maltase-glucoamylase, intestinal

General function:: Involved in catalytic activity
Specific function:: May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
Gene Name:: MGAM
Uniprot ID:: O43451
Molecular weight:: Not Available

Enzyme Details

9. Neutral alpha-glucosidase C

General function:: Involved in catalytic activity
Specific function:: Has alpha-glucosidase activity.
Gene Name:: GANC
Uniprot ID:: Q8TET4
Molecular weight:: Not Available

Enzyme Details

10. 14 kDa phosphohistidine phosphatase

General function:: Involved in phosphohistidine phosphatase activity
Specific function:: Exhibits phosphohistidine phosphatase activity.
Gene Name:: PHPT1
Uniprot ID:: Q9NRX4
Molecular weight:: Not Available

Only showing the first 10 proteins. There are 14 proteins in total.

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Showing Compound Card for D-Fructose (CDB004855)

Structure for CDB004855 (D-Fructose)

Enzymes