Cannabis Compound Database: Showing Compound Card for Xylulose 5-phosphate (CDB005249)

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Record Information

Version

1.0

Created at

2020-04-17 19:24:16 UTC

Updated at

2020-11-18 16:39:36 UTC

CannabisDB ID

CDB005249

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Xylulose 5-phosphate

Description

Xylulose 5-phosphate, also known as xylulose-p or xu-5-p, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. Xylulose 5-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Xylulose 5-phosphate exists in all living species, ranging from bacteria to humans. Within humans, xylulose 5-phosphate participates in a number of enzymatic reactions. In particular, xylulose 5-phosphate can be biosynthesized from D-ribulose 5-phosphate; which is catalyzed by the enzyme ribulose-phosphate 3-epimerase. In addition, D-ribose 5-phosphate and xylulose 5-phosphate can be biosynthesized from D-glyceraldehyde 3-phosphate and D-sedoheptulose 7-phosphate through the action of the enzyme transketolase. In humans, xylulose 5-phosphate is involved in pentose phosphate pathway. Outside of the human body, Xylulose 5-phosphate has been detected, but not quantified in, several different foods, such as parsnips, cabbages, common beets, celery stalks, and ostrich ferns. This could make xylulose 5-phosphate a potential biomarker for the consumption of these foods. The D-enantiomer of xylulose 5-phosphate. Xylulose 5-phosphate 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
5-O-Phosphono-D-threo-pentos-2-ulose	ChEBI
5-O-Phosphono-D-xylulose	ChEBI
D-Xylulose-5-phosphate	ChEBI
D-Xylulose-5-phosphoric acid	Generator
Xylulose 5-phosphoric acid	Generator
D-Xylulose 5-phosphate	HMDB
D-Xylulose 5-PO4	HMDB
D-Xylulose-5-P	HMDB
Xu-5-P	HMDB
Xylulose-P	HMDB
Xylulose-phosphate	HMDB
Xylulose-5-phosphate	MeSH, HMDB
Xylulose-5-phosphate, (D)-isomer	MeSH, HMDB
Xylulose 5-phosphate	HMDB
keto-D-Xylulose 5-phosphate	HMDB

Chemical Formula

C₅H₁₁O₈P

Average Molecular Weight

230.11

Monoisotopic Molecular Weight

230.0192

IUPAC Name

{[(2R,3S)-2,3,5-trihydroxy-4-oxopentyl]oxy}phosphonic acid

Traditional Name

ribulose-5-phosphate

CAS Registry Number

4212-65-1

SMILES

OCC(=O)[C@@H](O)[C@H](O)COP(O)(O)=O

InChI Identifier

InChI=1S/C5H11O8P/c6-1-3(7)5(9)4(8)2-13-14(10,11)12/h4-6,8-9H,1-2H2,(H2,10,11,12)/t4-,5-/m1/s1

InChI Key

FNZLKVNUWIIPSJ-RFZPGFLSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Monosaccharide phosphate
Monoalkyl phosphate
Acyloin
Beta-hydroxy ketone
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Alpha-hydroxy ketone
Ketone
Secondary alcohol
Polyol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Alcohol
Primary alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

xylulose 5-phosphate (CHEBI:16332 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

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	-1.8	ALOGPS
logP	-2.8	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	42.47 m³·mol⁻¹	ChemAxon
Polarizability	18.05 Å³	ChemAxon
Number of Rings	0	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	Xylulose 5-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0592-9800000000-d336b0e2eff1402939d8	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9023200000-1dd7d8e1f64921beb234	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Xylulose 5-phosphate, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - QTOF 4V, negative	splash10-004j-9170000000-997b74cb48ace33cccd6	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, negative	splash10-004j-9000000000-6bc02f4fe0074c9abd68	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, negative	splash10-004j-9000000000-bdadc167eb24a88aac33	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, negative	splash10-004j-9000000000-93d31d83892e88720b87	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, negative	splash10-004i-9000000000-10cd88e85162e6269751	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, negative	splash10-004i-9000000000-e9f2bf02f0d01a879d20	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, negative	splash10-004i-9000000000-732cd41f406b617c64a0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, negative	splash10-004i-9000000000-25a5607c50f3e9bb5a14	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 45V, negative	splash10-004i-9000000000-ea506b9429ed926c5f93	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 23V, negative	splash10-0002-9120000000-1172898b831a36b0afcb	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 25V, negative	splash10-0002-9110000000-132340cd62e8e4a0ccd2	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 27V, negative	splash10-0002-9110000000-297d4c6907686258e552	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 30V, negative	splash10-0002-9100000000-1cce49f995c912b1cc94	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 33V, negative	splash10-0002-9100000000-8bba2d7511cc9829eb36	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 35V, negative	splash10-0002-9100000000-89b3b4fdcb0326bfa0e0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 40V, negative	splash10-0002-9100000000-91e850ff1cd255a2f7fd	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QTOF 45V, negative	splash10-002b-9100000000-9c43f84a30add3ebce50	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 16V, negative	splash10-0002-9000000000-75847d481a06c31fa479	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 16V, negative	splash10-004i-0091000000-0af17cfb2eb7eab94967	2020-07-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-3790000000-6f5913e9948fa7667e41	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0btd-9710000000-3724bb9f611bbdc1fe11	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-8bc9cecb2dddad8ca5e3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9520000000-c36fdbcc1d3b19b2fafd	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-b67b8ea484aa4ddb40e3	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-82b17cf4f5a8c927fe64	2015-09-15	View Spectrum

NMR

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pentose Phosphate Pathway
Glucose-6-phosphate dehydrogenase deficiency		Not Available
Ribose-5-phosphate isomerase deficiency		Not Available
Transaldolase deficiency		Not Available
Warburg Effect		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Transketolase-like protein 1	TKTL1	Xq28	P51854	details
Transketolase	TKT	3p14.3	P29401	details
Xylulose kinase	XYLB	3p22-p21.3	O75191	details
Putative uncharacterized protein RPE	RPE	2q32-q33.3	Q53TV9	details
Ribulose-phosphate 3-epimerase	RPE	2q32-q33.3	Q96AT9	details
Transketolase-like protein 2	TKTL2	4q32.2	Q9H0I9	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Transketolase-like protein 1	TKTL1	Xq28	P51854	details
Ribulose-phosphate 3-epimerase	RPE	2q32-q33.3	Q96AT9	details
Transketolase-like protein 2	TKTL2	4q32.2	Q9H0I9	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000868

DrugBank ID

DB04034

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

Not Available

ChEBI ID

16332

References

General References

Not Available

Enzymes

Enzyme Details

1. Transketolase-like protein 1

General function:: Involved in catalytic activity
Specific function:: Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate (By similarity).
Gene Name:: TKTL1
Uniprot ID:: P51854
Molecular weight:: 59302.195

Enzyme Details

2. Transketolase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
Gene Name:: TKT
Uniprot ID:: P29401
Molecular weight:: 67876.95

Enzyme Details

3. Xylulose kinase

General function:: Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:: Not Available
Gene Name:: XYLB
Uniprot ID:: O75191
Molecular weight:: 58381.695

Enzyme Details

4. Putative uncharacterized protein RPE

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: RPE
Uniprot ID:: Q53TV9
Molecular weight:: 19537.4

Enzyme Details

5. Ribulose-phosphate 3-epimerase

General function:: Involved in catalytic activity
Specific function:: Catalyzes the reversible epimerization of D-ribulose 5-phosphate to D-xylulose 5-phosphate.
Gene Name:: RPE
Uniprot ID:: Q96AT9
Molecular weight:: 19537.385

Enzyme Details

6. Transketolase-like protein 2

General function:: Involved in catalytic activity
Specific function:: Plays an essential role in total transketolase activity and cell proliferation in cancer cells; after transfection with anti-TKTL1 siRNA, total transketolase activity dramatically decreases and proliferation was significantly inhibited in cancer cells. Plays a pivotal role in carcinogenesis.
Gene Name:: TKTL2
Uniprot ID:: Q9H0I9
Molecular weight:: 67876.625

Showing Compound Card for Xylulose 5-phosphate (CDB005249)

Structure for CDB005249 (Xylulose 5-phosphate)

Enzymes