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Showing metabocard for Adenosine 3',5'-diphosphate (HMDB00061)
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| Version | 3.6 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2005-11-16 15:48:42 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2017-03-02 21:25:36 UTC | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| HMDB ID | HMDB00061 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Metabolite Identification | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common Name | Adenosine 3',5'-diphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Adenosine 3', 5'-diphosphate or PAP is a nucleotide that is closely related to ADP. It has two phosphate groups attached to the 5' and 3' positions of the pentose sugar ribose (instead of pyrophosphoric acid at the 5' position, as found in ADP), and the nucleobase adenine. PAP is converted to PAPS by Sulfotransferase and then back to PAP after the sulfotransferase reaction. Sulfotransferase (STs) catalyze the transfer reaction of the sulfate group from the ubiquitous donor 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to an acceptor group of numerous substrates. This reaction, often referred to as sulfuryl transfer, sulfation, or sulfonation, is widely observed from bacteria to humans and plays a key role in various biological processes such as cell communication, growth and development, and defense. PAP also appears to a role in bipolar depression. Phosphatases converting 3'-phosphoadenosine 5'-phosphate (PAP) into adenosine 5'-phosphate are of fundamental importance in living cells as the accumulation of PAP is toxic to several cellular systems. These enzymes are lithium-sensitive and we have characterized a human PAP phosphatase as a potential target of lithium therapy. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
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| Chemical Formula | C10H15N5O10P2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight | 427.2011 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight | 427.029414749 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name | {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional Name | adenosine 3',5'-bisphosphate | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS Registry Number | 1053-73-2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES | NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H]1O | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Identifier | InChI=1S/C10H15N5O10P2/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(25-27(20,21)22)4(24-10)1-23-26(17,18)19/h2-4,6-7,10,16H,1H2,(H2,11,12,13)(H2,17,18,19)(H2,20,21,22)/t4-,6-,7-,10-/m1/s1 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | WHTCPDAXWFLDIH-KQYNXXCUSA-N | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | This compound belongs to the class of chemical entities known as purine ribonucleoside 3',5'-bisphosphates. These are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Chemical entities | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Nucleosides, nucleotides, and analogues | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Purine nucleotides | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Purine ribonucleoside 3',5'-bisphosphates | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents |
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| Substituents |
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| Molecular Framework | Aromatic heteropolycyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Ontology | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Status | Detected and Quantified | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Origin |
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| Biofunction |
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| Application | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular locations |
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| Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | Solid | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra |
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| Biological Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
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| Normal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Abnormal Concentrations | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Associated Disorders and Diseases | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Disease References | None | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Associated OMIM IDs | None | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank Metabolite ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Compound ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Metabolite ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FoodDB ID | FDB021887 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KNApSAcK ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemspider ID | 140102 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Compound ID | C00054 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | 3-5-ADP | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BiGG ID | 33684 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| NuGOwiki Link | HMDB00061 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Metagene Link | HMDB00061 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| METLIN ID | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PubChem Compound | 159296 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PDB ID | A3P | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | 17985 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference | Tsunako, Mitsutomo; Kotone, Akira. Preparation of nucleoside-2',5'- and 3',5'-diphosphoric acids. Jpn. Kokai Tokkyo Koho (1991), 13 pp. | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| General References |
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Enzymes
- General function:
- Involved in catalytic activity
- Specific function:
- Involved primarily in ATP hydrolysis at the plasma membrane. Plays a role in regulating pyrophosphate levels, and functions in bone mineralization and soft tissue calcification. In vitro, has a broad specificity, hydrolyzing other nucleoside 5' triphosphates such as GTP, CTP, TTP and UTP to their corresponding monophosphates with release of pyrophosphate and diadenosine polyphosphates, and also 3',5'-cAMP to AMP. May also be involved in the regulation of the availability of nucleotide sugars in the endoplasmic reticulum and Golgi, and the regulation of purinergic signaling. Appears to modulate insulin sensitivity.
- Gene Name:
- ENPP1
- Uniprot ID:
- P22413
- Molecular weight:
- 104923.58
Reactions
| Phosphoadenosine phosphosulfate + Water → Oat gum + Adenosine 3',5'-diphosphate | details |
- General function:
- Involved in catalytic activity
- Specific function:
- Cleaves a variety of phosphodiester and phosphosulfate bonds including deoxynucleotides, nucleotide sugars, and NAD (By similarity).
- Gene Name:
- ENPP3
- Uniprot ID:
- O14638
- Molecular weight:
- 100123.54
Reactions
| Phosphoadenosine phosphosulfate + Water → Oat gum + Adenosine 3',5'-diphosphate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues in desulfated dermatan sulfate. Preferentially sulfates in GlcA->GalNAc unit than in IdoA->GalNAc unit. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
- Gene Name:
- CHST11
- Uniprot ID:
- Q9NPF2
- Molecular weight:
- 41002.97
Reactions
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + chondroitin 4'-sulfate | details |
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + Chondroitin 4-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Can also sulfate Gal residues of keratan sulfate, another glycosaminoglycan, and the Gal residues in sialyl N-acetyllactosamine (sialyl LacNAc) oligosaccharides. May play a role in the maintenance of naive T-lymphocytes in the spleen.
- Gene Name:
- CHST3
- Uniprot ID:
- Q7LGC8
- Molecular weight:
- 54705.5
Reactions
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + Chondroitin 6'-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Transfers sulfate to the C4 hydroxyl of beta1,4-linked GalNAc that is substituted with a beta-linked glucuronic acid at the C-3 hydroxyl. No activity toward dermatan.
- Gene Name:
- CHST13
- Uniprot ID:
- Q8NET6
- Molecular weight:
- 38919.34
Reactions
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + chondroitin 4'-sulfate | details |
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + Chondroitin 4-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of chondroitin and desulfated dermatan sulfate. Chondroitin sulfate constitutes the predominant proteoglycan present in cartilage and is distributed on the surfaces of many cells and extracellular matrices. Activity toward partially desulfated dermatan sulfate is however lower. Does not form 4, 6-di-O-sulfated GalNAc when chondroitin sulfate C is used as an acceptor.
- Gene Name:
- CHST12
- Uniprot ID:
- Q9NRB3
- Molecular weight:
- 48413.945
Reactions
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + chondroitin 4'-sulfate | details |
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + Chondroitin 4-sulfate | details |
- General function:
- Involved in galactosylceramide sulfotransferase activity
- Specific function:
- Catalyzes the sulfation of membrane glycolipids. Seems to prefer beta-glycosides at the non-reducing termini of sugar chains attached to a lipid moiety. Catalyzes the synthesis of galactosylceramide sulfate (sulfatide), a major lipid component of the myelin sheath and of monogalactosylalkylacylglycerol sulfate (seminolipid), present in spermatocytes (By similarity). Also acts on lactosylceramide, galactosyl 1-alkyl-2-sn-glycerol and galactosyl diacylglycerol (in vitro).
- Gene Name:
- GAL3ST1
- Uniprot ID:
- Q99999
- Molecular weight:
- 48763.63
Reactions
| Phosphoadenosine phosphosulfate + a galactosylceramide → Adenosine 3',5'-diphosphate + a galactosylceramidesulfate | details |
| Phosphoadenosine phosphosulfate + monogalactosylalkylacylglycerol → Adenosine 3',5'-diphosphate + monogalactosylalkylacylglycerol sulfate | details |
| Phosphoadenosine phosphosulfate + Galactosylceramide → Adenosine 3',5'-diphosphate + Sulfatide | details |
| Phosphoadenosine phosphosulfate + Digalactosylceramide → Adenosine 3',5'-diphosphate + Digalactosylceramidesulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in IdoUA2S-GlcNS and also in IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
- Gene Name:
- HS3ST3B1
- Uniprot ID:
- Q9Y662
- Molecular weight:
- 43323.605
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in IdoUA2S-GlcNS and also in IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
- Gene Name:
- HS3ST3A1
- Uniprot ID:
- Q9Y663
- Molecular weight:
- 44899.155
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
- Gene Name:
- SULT1A1
- Uniprot ID:
- P50225
- Molecular weight:
- 34165.13
Reactions
| Phosphoadenosine phosphosulfate + a phenol → Adenosine 3',5'-diphosphate + an aryl sulfate | details |
| Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphate | details |
- 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
Reactions
| Adenosine 3',5'-diphosphate + Water → Adenosine monophosphate + Phosphoric acid | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to position 3 of glucosamine residues in heparan. Catalyzes the rate limiting step in the biosynthesis of heparan sulfate (HSact). This modification is a crucial step in the biosynthesis of anticoagulant heparan sulfate as it completes the structure of the antithrombin pentasaccharide binding site.
- Gene Name:
- HS3ST1
- Uniprot ID:
- O14792
- Molecular weight:
- 35772.77
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
- Gene Name:
- SULT1E1
- Uniprot ID:
- P49888
- Molecular weight:
- 35126.185
Reactions
| Phosphoadenosine phosphosulfate + Estrone → Adenosine 3',5'-diphosphate + Estrone sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfonation of steroids and bile acids in the liver and adrenal glands.
- Gene Name:
- SULT2A1
- Uniprot ID:
- Q06520
- Molecular weight:
- 33779.57
Reactions
| Phosphoadenosine phosphosulfate + Lithocholic acid glycine conjugate → Adenosine 3',5'-diphosphate + Sulfolithocholylglycine | details |
| Phosphoadenosine phosphosulfate + Lithocholyltaurine → Adenosine 3',5'-diphosphate + Taurolithocholic acid 3-sulfate | details |
| 7-Hydroxymethyl-12-methylbenz[a]anthracene + Phosphoadenosine phosphosulfate → 7-Hydroxymethyl-12-methylbenz[a]anthracene sulfate + Adenosine 3',5'-diphosphate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of galactose (Gal) residues of keratan. Has a preference for sulfating keratan sulfate, but it also transfers sulfate to the unsulfated polymer. The sulfotransferase activity on sialyl LacNAc structures is much higher than the corresponding desialylated substrate, and only internal Gal residues are sulfated. May function in the sulfation of sialyl N-acetyllactosamine oligosaccharide chains attached to glycoproteins. Participates in biosynthesis of selectin ligands. Selectin ligands are present in high endothelial cells (HEVs) and play a central role in lymphocyte homing at sites of inflammation.
- Gene Name:
- CHST1
- Uniprot ID:
- O43916
- Molecular weight:
- 46714.21
Reactions
| Phosphoadenosine phosphosulfate + Keratan → Adenosine 3',5'-diphosphate + Keratan | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate (By similarity).
- Gene Name:
- HS3ST4
- Uniprot ID:
- Q9Y661
- Molecular weight:
- 49798.645
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Is also responsible for the sulfonation and activation of minoxidil. Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
- Gene Name:
- SULT1A2
- Uniprot ID:
- P50226
- Molecular weight:
- 34310.43
Reactions
| Phosphoadenosine phosphosulfate + a phenol → Adenosine 3',5'-diphosphate + an aryl sulfate | details |
| Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to position 3 of glucosamine residues in heparan. Catalyzes the rate limiting step in the biosynthesis of heparan sulfate (HSact). This modification is a crucial step in the biosynthesis of anticoagulant heparan sulfate as it completes the structure of the antithrombin pentasaccharide binding site. Also generates GlcUA-GlcNS or IdoUA-GlcNS and IdoUA2S-GlcNH2. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes simplex virus-1 (HSV-1) and permits its entry.
- Gene Name:
- HS3ST5
- Uniprot ID:
- Q8IZT8
- Molecular weight:
- 40407.865
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to an N-unsubstituted glucosamine linked to a 2-O-sulfo iduronic acid unit on heparan sulfate. Catalyzes the O-sulfation of glucosamine in GlcA2S-GlcNS. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
- Gene Name:
- HS3ST2
- Uniprot ID:
- Q9Y278
- Molecular weight:
- 41500.57
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Catalyzes the O-sulfation of tyrosine residues within acidic motifs of polypeptides.
- Gene Name:
- TPST2
- Uniprot ID:
- O60704
- Molecular weight:
- 41911.47
Reactions
| Phosphoadenosine phosphosulfate + protein tyrosine → Adenosine 3',5'-diphosphate + protein tyrosine-O-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
- Gene Name:
- SULT2B1
- Uniprot ID:
- O00204
- Molecular weight:
- 39598.595
Reactions
| Phosphoadenosine phosphosulfate + an alcohol → Adenosine 3',5'-diphosphate + an alkyl sulfate | details |
| Alcohol + Phosphoadenosine phosphosulfate → Alkyl sulfate + Adenosine 3',5'-diphosphate | details |
| Phosphoadenosine phosphosulfate + Dehydroepiandrosterone → Adenosine 3',5'-diphosphate + Dehydroepiandrosterone sulfate | details |
| Cholesterol + Phosphoadenosine phosphosulfate → Cholesterol sulfate + Adenosine 3',5'-diphosphate | details |
| Pregnenolone + Phosphoadenosine phosphosulfate → 3beta-Hydroxypregn-5-en-20-one sulfate + Adenosine 3',5'-diphosphate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
- Gene Name:
- SULT1A3
- Uniprot ID:
- P50224
- Molecular weight:
- 34195.96
Reactions
| Phosphoadenosine phosphosulfate + a phenol → Adenosine 3',5'-diphosphate + an aryl sulfate | details |
| Phosphoadenosine phosphosulfate + Phenol → Adenosine 3',5'-diphosphate + Phenol sulphate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the transfer of sulfate to position 6 of non-reducing N-acetylglucosamine (GlcNAc) residues. Preferentially acts on mannose-linked GlcNAc. Also able to catalyze the transfer of sulfate to position 6 of the N-acetylgalactosamine (GalNAc) residue of chondroitin. Also acts on core 2 mucin-type oligosaccharide and N-acetyllactosamine oligomer with a lower efficiency. Has weak or no activity toward keratan sulfate and oligosaccharides containing the Galbeta1-4GlcNAc. Catalyzes 6-O-sulfation of beta-benzyl GlcNAc but not alpha- or beta-benzyl GalNAc.
- Gene Name:
- CHST7
- Uniprot ID:
- Q9NS84
- Molecular weight:
- 54265.635
Reactions
| Phosphoadenosine phosphosulfate + Chondroitin → Adenosine 3',5'-diphosphate + Chondroitin 6'-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Catalyzes the transfer of sulfate to position 4 of the N-acetylgalactosamine (GalNAc) residue of dermatan sulfate. Plays a pivotal role in the formation of 4-0-sulfated IdoA blocks in dermatan sulfate. Transfers sulfate to the C-4 hydroxyl of beta1,4-linked GalNAc that is substituted with an alpha-linked iduronic acid (IdoUA) at the C-3 hydroxyl. Transfers sulfate more efficiently to GalNAc residues in -IdoUA-GalNAc-IdoUA- than in -GlcUA-GalNAc-GlcUA-sequences. Has preference for partially desulfated dermatan sulfate. Addition of sulfate to GalNAc may occur immediately after epimerization of GlcUA to IdoUA. GlcUA to IdoUA. Appears to have an important role in the formation of the cerbellar neural network during postnatal brain development.
- Gene Name:
- CHST14
- Uniprot ID:
- Q8NCH0
- Molecular weight:
- 42996.535
Reactions
| Phosphoadenosine phosphosulfate + [dermatan]-N-acetyl-D-galactosamine → Adenosine 3',5'-diphosphate + [dermatan]- 4-O-sulfo-N-acetyl-D-galactosamine | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- 6-O-sulfation enzyme which catalyzes the transfer of sulfate from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to position 6 of the N-sulfoglucosamine residue (GlcNS) of heparan sulfate.
- Gene Name:
- HS6ST1
- Uniprot ID:
- O60243
- Molecular weight:
- 48225.71
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 6-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- 6-O-sulfation enzyme which catalyzes the transfer of sulfate from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to position 6 of the N-sulfoglucosamine residue (GlcNS) of heparan sulfate.
- Gene Name:
- HS6ST2
- Uniprot ID:
- Q96MM7
- Molecular weight:
- 73389.99
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 6-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- 6-O-sulfation enzyme which catalyzes the transfer of sulfate from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to position 6 of the N-sulfoglucosamine residue (GlcNS) of heparan sulfate.
- Gene Name:
- HS6ST3
- Uniprot ID:
- Q8IZP7
- Molecular weight:
- 54843.27
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 6-sulfate | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Sulfotransferase that transfers sulfate from 3'-phosphoadenosine 5'-phosphosulfate (PAPS) to the C-6 hydroxyl group of the GalNAc 4-sulfate residue of chondroitin sulfate A and forms chondroitin sulfate E containing GlcA-GalNAc(4,6-SO(4)) repeating units. It also transfers sulfate to a unique non-reducing terminal sequence, GalNAc(4SO4)-GlcA(2SO4)-GalNAc(6SO4), to yield a highly sulfated structure similar to the structure found in thrombomodulin chondroitin sulfate. May also act as a B-cell receptor involved in BCR ligation-mediated early activation that mediate regulatory signals key to B-cell development and/or regulation of B-cell-specific RAG expression; however such results are unclear in vivo.
- Gene Name:
- CHST15
- Uniprot ID:
- Q7LFX5
- Molecular weight:
- 64925.66
Reactions
| 3-phospho-5-adenylyl sulfate + [dermatan]-4-O-sulfo-N-acetylgalactosamine → Adenosine 3',5'-diphosphate + [dermatan]-4,6-di-O-sulfo-N-acetyl-D-galactosamine | details |
| 3-phospho-5-adenylyl sulfate + [chondroitin]-4-O-sulfo-N-acetylgalactosamine → Adenosine 3',5'-diphosphate + [chondroitin]-4,6-di-O-sulfo-N-acetyl-D-galactosamine | details |
- 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
Reactions
| Adenosine 3',5'-diphosphate + Water → Adenosine monophosphate + Phosphoric acid | details |
- General function:
- Involved in sulfotransferase activity
- Specific function:
- Not Available
- Gene Name:
- TPST1
- Uniprot ID:
- A4D2M0
- Molecular weight:
- 42188.1
- General function:
- Involved in magnesium ion binding
- Specific function:
- Catalyzes the post-translational modification of target proteins by phosphopantetheine. Can transfer the 4'-phosphopantetheine moiety from coenzyme A to a serine residue of a broad range of acceptors, such as the acyl carrier domain of FASN.
- Gene Name:
- AASDHPPT
- Uniprot ID:
- Q9NRN7
- Molecular weight:
- 35775.64
Reactions
| CoA-[4'-phosphopantetheine] + apo-[acyl-carrier-protein] → Adenosine 3',5'-diphosphate + holo-[acyl-carrier-protein] | details |
| Coenzyme A + Apo-[acyl-carrier-protein] → Adenosine 3',5'-diphosphate + Acyl-carrier protein | details |
- General function:
- Not Available
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) to catalyze the transfer of a sulfo group to heparan sulfate. The substrate-specific O-sulfation generates an enzyme-modified heparan sulfate which acts as a binding receptor to Herpes Simplex Virus-1 (HSV-1) and permits its entry. Unlike 3-OST-1, does not convert non-anticoagulant heparan sulfate to anticoagulant heparan sulfate.
- Gene Name:
- HS3ST6
- Uniprot ID:
- Q96QI5
- Molecular weight:
- Not Available
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-glucosamine 3-sulfate | details |
- General function:
- Not Available
- Specific function:
- Essential bifunctional enzyme that catalyzes both the N-deacetylation and the N-sulfation of glucosamine (GlcNAc) of the glycosaminoglycan in heparan sulfate. Modifies the GlcNAc-GlcA disaccharide repeating sugar backbone to make N-sulfated heparosan, a prerequisite substrate for later modifications in heparin biosynthesis. Plays a role in determining the extent and pattern of sulfation of heparan sulfate. Compared to other NDST enzymes, its presence is absolutely required. Participates in biosynthesis of heparan sulfate that can ultimately serve as L-selectin ligands, thereby playing a role in inflammatory response.
- Gene Name:
- NDST1
- Uniprot ID:
- P52848
- Molecular weight:
- 100867.015
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosamine | details |
- General function:
- Not Available
- Specific function:
- Essential bifunctional enzyme that catalyzes both the N-deacetylation and the N-sulfation of glucosamine (GlcNAc) of the glycosaminoglycan in heparan sulfate. Modifies the GlcNAc-GlcA disaccharide repeating sugar backbone to make N-sulfated heparosan, a prerequisite substrate for later modifications in heparin biosynthesis. Plays a role in determining the extent and pattern of sulfation of heparan sulfate.
- Gene Name:
- NDST2
- Uniprot ID:
- P52849
- Molecular weight:
- 100873.72
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosamine | details |
- General function:
- Not Available
- Specific function:
- Essential bifunctional enzyme that catalyzes both the N-deacetylation and the N-sulfation of glucosamine (GlcNAc) of the glycosaminoglycan in heparan sulfate. Modifies the GlcNAc-GlcA disaccharide repeating sugar backbone to make N-sulfated heparosan, a prerequisite substrate for later modifications in heparin biosynthesis. Has high deacetylase activity but low sulfotransferase activity.
- Gene Name:
- NDST3
- Uniprot ID:
- O95803
- Molecular weight:
- 100901.23
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosamine | details |
- General function:
- Not Available
- Specific function:
- Essential bifunctional enzyme that catalyzes both the N-deacetylation and the N-sulfation of glucosamine (GlcNAc) of the glycosaminoglycan in heparan sulfate. Modifies the GlcNAc-GlcA disaccharide repeating sugar backbone to make N-sulfated heparosan, a prerequisite substrate for later modifications in heparin biosynthesis. Has low deacetylase activity but high sulfotransferase activity (By similarity).
- Gene Name:
- NDST4
- Uniprot ID:
- Q9H3R1
- Molecular weight:
- 100714.905
Reactions
| Phosphoadenosine phosphosulfate + [heparan sulfate]-glucosamine → Adenosine 3',5'-diphosphate + [heparan sulfate]-N-sulfoglucosamine | details |
- General function:
- Not Available
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor and has low sulphotransferase activity towards various substrates with alcohol groups (in vitro). May catalyze the sulfate conjugation of xenobiotic compounds and endogenous substrates.
- Gene Name:
- SULT1C3
- Uniprot ID:
- Q6IMI6
- Molecular weight:
- 35888.345
Reactions
| Phosphoadenosine phosphosulfate + an alcohol → Adenosine 3',5'-diphosphate + an alkyl sulfate | details |
- General function:
- Not Available
- Specific function:
- Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of thyroxine. Involved in the metabolism of thyroxine (By similarity).
- Gene Name:
- SULT6B1
- Uniprot ID:
- Q6IMI4
- Molecular weight:
- Not Available
Reactions
| Phosphoadenosine phosphosulfate + Thyroxine → Adenosine 3',5'-diphosphate + thyroxine-sulfate | details |
- General function:
- Not Available
- Specific function:
- Catalyzes the O-sulfation of tyrosine residues within acidic motifs of polypeptides.
- Gene Name:
- TPST1
- Uniprot ID:
- O60507
- Molecular weight:
- 42188.075
Reactions
| Phosphoadenosine phosphosulfate + protein tyrosine → Adenosine 3',5'-diphosphate + protein tyrosine-O-sulfate | details |