Cannabis Compound Database: Showing Compound Card for Adenosine phosphosulfate (CDB005301)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (5) Show 6 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:29:26 UTC

Updated at

2020-11-18 16:39:41 UTC

CannabisDB ID

CDB005301

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Adenosine phosphosulfate

Description

Adenosine phosphosulfate, also known as adenylylsulfate or adenosine sulfatophosphate, belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenosine phosphosulfate is a strong basic compound (based on its pKa). Adenosine phosphosulfate exists in all living species, ranging from bacteria to humans. Within humans, adenosine phosphosulfate participates in a number of enzymatic reactions. In particular, adenosine phosphosulfate can be biosynthesized from sulfate through the action of the enzyme bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2. In addition, adenosine phosphosulfate can be converted into phosphoadenosine phosphosulfate; which is catalyzed by the enzyme bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2. In humans, adenosine phosphosulfate is involved in sulfate/sulfite metabolism. Outside of the human body, Adenosine phosphosulfate has been detected, but not quantified in, several different foods, such as chia, yardlong beans, swiss chards, sapodilla, and chicory leaves. This could make adenosine phosphosulfate a potential biomarker for the consumption of these foods. An adenosine 5'-phosphate having a sulfo group attached to one the phosphate OH groups. Adenosine phosphosulfate 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
Adenosine 5'-phosphosulfate	ChEBI
ADENOSINE-5'-phosphosulfATE	ChEBI
Adenylylsulfate	ChEBI
APS	ChEBI
5'-Adenylyl sulfate	Kegg
Adenosine 5'-phosphosulfuric acid	Generator
Adenosine 5'-phosphosulphate	Generator
Adenosine 5'-phosphosulphuric acid	Generator
ADENOSINE-5'-phosphosulfuric acid	Generator
ADENOSINE-5'-phosphosulphate	Generator
ADENOSINE-5'-phosphosulphuric acid	Generator
Adenylylsulfuric acid	Generator
Adenylylsulphate	Generator
Adenylylsulphuric acid	Generator
5'-Adenylyl sulfuric acid	Generator
5'-Adenylyl sulphate	Generator
5'-Adenylyl sulphuric acid	Generator
Adenosine phosphosulfuric acid	Generator
Adenosine phosphosulphate	Generator
Adenosine phosphosulphuric acid	Generator
Adenosine 5'-sulphatophosphate	HMDB
Adenosine sulfatophosphate	HMDB
Adenylic acid monoanhydride with sulfurate	HMDB
Adenylic acid monoanhydride with sulfuric acid	HMDB
Adenylyl sulfate	HMDB
Adenylyl sulphate	HMDB
Adenylyl-sulfate	HMDB
Adenylyl-sulphate	HMDB
AMPS	HMDB
Phosphosulfate	HMDB
Phosphosulphate	HMDB
Sulfatophosphate	HMDB
5'-Phosphosulfate, adenosine	HMDB
Adenosine 5' phosphosulfate	HMDB
Phospho adenylsulfate	HMDB
Phospho-adenylsulfate	HMDB
Phosphosulfate, adenosine	HMDB
Sulfate, adenylyl	HMDB
5’-Adenylyl sulfate	HMDB
5’-Adenylyl sulphate	HMDB
Adenosine 5'-monophosphosulfate	HMDB
Adenosine 5'-monophosphosulphate	HMDB
Adenosine 5'-sulfatophosphate	HMDB
Adenosine 5’-monophosphosulfate	HMDB
Adenosine 5’-monophosphosulphate	HMDB
Adenosine 5’-phosphosulfate	HMDB
Adenosine 5’-phosphosulphate	HMDB
Adenosine 5’-sulfatophosphate	HMDB

Chemical Formula

C₁₀H₁₄N₅O₁₀PS

Average Molecular Weight

427.28

Monoisotopic Molecular Weight

427.0199

IUPAC Name

[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid

Traditional Name

adenosine phosphosulfate

CAS Registry Number

485-84-7

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OS(O)(=O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C10H14N5O10PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1

InChI Key

IRLPACMLTUPBCL-KQYNXXCUSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as purine ribonucleoside monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

Purine ribonucleoside monophosphates

Alternative Parents

Substituents

Purine ribonucleoside monophosphate
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
Pyrimidine
Monosaccharide
Imidolactam
Phosphoric acid ester
N-substituted imidazole
Organic phosphoric acid derivative
Tetrahydrofuran
Heteroaromatic compound
Azole
Imidazole
Organic sulfuric acid or derivatives
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Amine
Alcohol
Primary amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

adenosine 5'-phosphate (CHEBI:17709 )
acyl sulfate (CHEBI:17709 )
acyl monophosphate (CHEBI:17709 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Organ and components:

Cell and elements:

Cell:

Fibroblast

Element:

Platelet

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	-1.6	ALOGPS
logP	-5.6	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	3.94	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	229.44 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	84.06 m³·mol⁻¹	ChemAxon
Polarizability	35.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Adenosine phosphosulfate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-2911100000-c7b3ba6ec47b4fb3e832	Spectrum
Predicted GC-MS	Adenosine phosphosulfate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-055b-7693530000-45cc4add4821e6fea5ef	Spectrum
Predicted GC-MS	Adenosine phosphosulfate, non-derivatized, 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	splash10-000i-0912300000-29cd6f42fa9d4c6c4455	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0901000000-018ae7ee1fc1b662ec07	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1900000000-861a01467a0191dcd31a	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0059-0901600000-785b903b29133cefd0bc	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-3900000000-d2245ba9a6f6bf6d0217	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-9700000000-3f4588ade18801775bec	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0200900000-b10f97ec4ef8bff7823c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0911000000-4563fb5a2cb7fd85ab98	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0900000000-5a937b62fdf69d198700	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0100900000-a398ce6fc250a971f068	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-6900300000-d9d41d4bc70263df8221	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004j-9200000000-979bc3001281c5d76962	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Sulfate/Sulfite Metabolism
Sulfite oxidase deficiency		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
3'(2'),5'-bisphosphate nucleotidase 1	BPNT1	1q41	O95861	details
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1	PAPSS1	4q24	O43252	details
Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2	PAPSS2	10q24	O95340	details
Adenosine 3'-phospho 5'-phosphosulfate transporter 1	SLC35B2	6p12.1-p11.2	Q8TB61	details
Inositol monophosphatase 3	IMPAD1	8q12.1	Q9NX62	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Inositol monophosphatase 3	IMPAD1	8q12.1	Q9NX62	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001003

DrugBank ID

DB03708

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

5933

PubChem Compound

10238

PDB ID

Not Available

ChEBI ID

17709

References

General References

Not Available

Enzymes

Enzyme Details

1. 3'(2'),5'-bisphosphate nucleotidase 1

General function:: Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:: Converts adenosine 3'-phosphate 5'-phosphosulfate (PAPS) to adenosine 5'-phosphosulfate (APS) and 3'(2')-phosphoadenosine 5'- phosphate (PAP) to AMP. Has 1000-fold lower activity towards inositol 1,4-bisphosphate (Ins(1,4)P2) and inositol 1,3,4-trisphosphate (Ins(1,3,4)P3), but does not hydrolyze Ins(1)P, Ins(3,4)P2, Ins(1,3,4,5)P4 or InsP6.
Gene Name:: BPNT1
Uniprot ID:: O95861
Molecular weight:: 33392.035

Enzyme Details

2. Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 1

General function:: Involved in ATP binding
Specific function:: Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. Also involved in the biosynthesis of sulfated L-selectin ligands in endothelial cells.
Gene Name:: PAPSS1
Uniprot ID:: O43252
Molecular weight:: 70832.725

Enzyme Details

3. Bifunctional 3'-phosphoadenosine 5'-phosphosulfate synthase 2

General function:: Involved in ATP binding
Specific function:: Bifunctional enzyme with both ATP sulfurylase and APS kinase activity, which mediates two steps in the sulfate activation pathway. The first step is the transfer of a sulfate group to ATP to yield adenosine 5'-phosphosulfate (APS), and the second step is the transfer of a phosphate group from ATP to APS yielding 3'-phosphoadenylylsulfate (PAPS: activated sulfate donor used by sulfotransferase). In mammals, PAPS is the sole source of sulfate; APS appears to be only an intermediate in the sulfate-activation pathway. May have a important role in skeletogenesis during postnatal growth (By similarity).
Gene Name:: PAPSS2
Uniprot ID:: O95340
Molecular weight:: 69969.8

Enzyme Details

4. Adenosine 3'-phospho 5'-phosphosulfate transporter 1

General function:: Involved in transmembrane transport
Specific function:: Mediates the transport of adenosine 3'-phospho 5'- phosphosulfate (PAPS), from cytosol into Golgi. PAPS is a universal sulfuryl donor for sulfation events that take place in the Golgi. May indirectly participate in activation of the NF- kappa-B and MAPK pathways
Gene Name:: SLC35B2
Uniprot ID:: Q8TB61
Molecular weight:: 47514.3

Enzyme Details

5. Inositol monophosphatase 3

General function:: Involved in inositol or phosphatidylinositol phosphatase activity
Specific function:: May play a role in the formation of skeletal elements derived through endochondral ossification, possibly by clearing adenosine 3',5'-bisphosphate produced by Golgi sulfotransferases during glycosaminoglycan sulfation (By similarity).
Gene Name:: IMPAD1
Uniprot ID:: Q9NX62
Molecular weight:: 38681.15

Showing Compound Card for Adenosine phosphosulfate (CDB005301)

Structure for CDB005301 (Adenosine phosphosulfate)

Enzymes