Cannabis Compound Database: Showing Compound Card for D-Erythrose 4-phosphate (CDB005160)

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Record Information

Version

1.0

Created at

2020-04-17 19:15:22 UTC

Updated at

2020-11-18 16:39:27 UTC

CannabisDB ID

CDB005160

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

D-Erythrose 4-phosphate

Description

D-Erythrose 4-phosphate, also known as D-erythrose-4-p or 4-O-phosphono-D-erythrose, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. D-Erythrose 4-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Erythrose 4-phosphate exists in all living species, ranging from bacteria to humans. Within humans, D-erythrose 4-phosphate participates in a number of enzymatic reactions. In particular, D-erythrose 4-phosphate and fructose 6-phosphate can be converted into D-glyceraldehyde 3-phosphate and D-sedoheptulose 7-phosphate; which is catalyzed by the enzyme transaldolase. In addition, D-erythrose 4-phosphate and xylulose 5-phosphate can be converted into fructose 6-phosphate and D-glyceraldehyde 3-phosphate through its interaction with the enzyme transketolase. In humans, D-erythrose 4-phosphate is involved in the metabolic disorder called the glucose-6-phosphate dehydrogenase deficiency pathway. D-Erythrose 4-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
4-O-Phosphono-D-erythrose	ChEBI
Erythose-4-phosphate	ChEBI
D-Erythrose 4-phosphoric acid	Generator
Erythose-4-phosphoric acid	Generator
D-Erythrose 4-PO4	HMDB
D-Erythrose-4-P	HMDB
D-Erythrose-4-phosphate	HMDB
Erythrose 4-phosphate	HMDB, MeSH
Erythrose 4-PO4	HMDB
Erythrose-4-P	HMDB
Erythrose-4-phosphate	HMDB
Erythrose-4P	HMDB
Threose 4-phosphate	HMDB, MeSH
Erythrose 4-phosphate, (r,r)-isomer	MeSH, HMDB
Erythrose 4-phosphate, ((r,r)-(+-))-isomer	MeSH, HMDB
(2R,3R)-2,3-Dihydroxy-4-(phosphonooxy)butanal	HMDB
D-Erythrose 4-phosphate	HMDB

Chemical Formula

C₄H₉O₇P

Average Molecular Weight

200.08

Monoisotopic Molecular Weight

200.0086

IUPAC Name

[(2R,3R)-2,3-dihydroxy-4-oxobutoxy]phosphonic acid

Traditional Name

4-O-phosphono-D-erythrose

CAS Registry Number

585-18-2

SMILES

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

InChI Identifier

InChI=1S/C4H9O7P/c5-1-3(6)4(7)2-11-12(8,9)10/h1,3-4,6-7H,2H2,(H2,8,9,10)/t3-,4+/m0/s1

InChI Key

NGHMDNPXVRFFGS-IUYQGCFVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Monosaccharide phosphates

Alternative Parents

Substituents

Monosaccharide phosphate
Monoalkyl phosphate
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Beta-hydroxy aldehyde
Alpha-hydroxyaldehyde
Secondary alcohol
1,2-diol
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aldehyde
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

erythrose phosphate (CHEBI:48153 )

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	-1.9	ALOGPS
logP	-2.4	ChemAxon
logS	-0.93	ALOGPS
pKa (Strongest Acidic)	1.48	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	36.29 m³·mol⁻¹	ChemAxon
Polarizability	15.41 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
GC-MS	D-Erythrose 4-phosphate, 1 MEOX; 4 TMS, GC-MS Spectrum	splash10-0a4i-2946000000-9443f2e925fd6a35c72c	Spectrum
GC-MS	D-Erythrose 4-phosphate, 1 MEOX; 4 TMS, GC-MS Spectrum	splash10-0a4i-2967000000-d813d71e392e180e1a1a	Spectrum
GC-MS	D-Erythrose 4-phosphate, non-derivatized, GC-MS Spectrum	splash10-0a4i-2946000000-9443f2e925fd6a35c72c	Spectrum
GC-MS	D-Erythrose 4-phosphate, non-derivatized, GC-MS Spectrum	splash10-0a4i-2967000000-d813d71e392e180e1a1a	Spectrum
GC-MS	D-Erythrose 4-phosphate, non-derivatized, GC-MS Spectrum	splash10-0pba-1933000000-ce3489351efc49bf69f3	Spectrum
GC-MS	D-Erythrose 4-phosphate, non-derivatized, GC-MS Spectrum	splash10-0ka2-2923000000-16fa49e06a727e2d6a47	Spectrum
Predicted GC-MS	D-Erythrose 4-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9600000000-9d57877fd2f223b326b3	Spectrum
Predicted GC-MS	D-Erythrose 4-phosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01di-8973000000-4793f4bb7564afb5ca7b	Spectrum
Predicted GC-MS	D-Erythrose 4-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002b-9000000000-06d71bced6df9b8baad3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-0f89-0069000000-8e4338affc4361b89493	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, positive	splash10-0uk9-0690000000-30a248b95eee8bfd3014	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ue9-3940000000-b2cf1408c63fcd508190	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-114m-9800000000-ca839aa0d4b5ed1d26a8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052v-9100000000-ce3e3be16de64b5ce20e	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-054k-8900000000-951c8d2dad21e2f2c479	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-4106e1504853e25f6dff	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-150345a1ab7b74a502c9	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9010000000-1278b7bf699cdfb2fc5e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9000000000-db5a64d3322c49bfb840	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9000000000-bab6e7f750d40a012094	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002b-9000000000-4212adf2abc696a02cdb	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9000000000-c47fda1609169ecd31ba	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-25	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
Transaldolase	TALDO1	11p15.5-p15.4	P37837	details
Transketolase	TKT	3p14.3	P29401	details
Fructose-bisphosphate aldolase A	ALDOA	16p11.2	P04075	details
Fructose-bisphosphate aldolase C	ALDOC	17cen-q12	P09972	details
Fructose-bisphosphate aldolase B	ALDOB	9q21.3-q22.2	P05062	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
Transketolase-like protein 2	TKTL2	4q32.2	Q9H0I9	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001321

DrugBank ID

DB03937

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Erythrose_4-phosphate

METLIN ID

6158

PubChem Compound

122357

PDB ID

Not Available

ChEBI ID

48153

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. Transaldolase

General function:: Involved in catalytic activity
Specific function:: Transaldolase is important for the balance of metabolites in the pentose-phosphate pathway.
Gene Name:: TALDO1
Uniprot ID:: P37837
Molecular weight:: 37539.74

Enzyme Details

3. 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

4. Fructose-bisphosphate aldolase A

General function:: Involved in fructose-bisphosphate aldolase activity
Specific function:: Plays a key role in glycolysis and gluconeogenesis. In addition, may also function as scaffolding protein (By similarity).
Gene Name:: ALDOA
Uniprot ID:: P04075
Molecular weight:: 39419.675

Enzyme Details

5. Fructose-bisphosphate aldolase C

General function:: Involved in fructose-bisphosphate aldolase activity
Specific function:: Not Available
Gene Name:: ALDOC
Uniprot ID:: P09972
Molecular weight:: 39455.505

Enzyme Details

6. Fructose-bisphosphate aldolase B

General function:: Involved in fructose-bisphosphate aldolase activity
Specific function:: Not Available
Gene Name:: ALDOB
Uniprot ID:: P05062
Molecular weight:: 39472.715

Enzyme Details

7. 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 D-Erythrose 4-phosphate (CDB005160)

Structure for CDB005160 (D-Erythrose 4-phosphate)

Enzymes