Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2021-09-24 09:58:54 UTC |
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Update Date | 2021-09-24 09:58:54 UTC |
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HMDB ID | HMDB0304464 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | phosphoadenosine-5'-phosphosulfate |
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Description | Phosphoadenosine-5'-phosphosulfate, also known as paps or 3'-phosphonato-5'-adenylyl sulfate, is a member of the class of compounds known as purine ribonucleoside 3',5'-bisphosphates. Purine ribonucleoside 3',5'-bisphosphates are purine ribobucleotides with one phosphate group attached to 3' and 5' hydroxyl groups of the ribose moiety. Phosphoadenosine-5'-phosphosulfate is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Phosphoadenosine-5'-phosphosulfate can be found in a number of food items such as cloves, abiyuch, cocoa bean, and jute, which makes phosphoadenosine-5'-phosphosulfate a potential biomarker for the consumption of these food products. |
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Structure | [H][C@]1(COP([O-])(=O)OS([O-])(=O)=O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/p-4/t4-,6-,7-,10-/m1/s1 |
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Synonyms | Value | Source |
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3'-Phosphoadenylyl sulfate | ChEBI | 3'-Phosphonato-5'-adenylyl sulfate | ChEBI | 3'-Phosphonato-5'-adenylyl sulfate tetraanion | ChEBI | 3'-Phosphonatoadenosine 5'-phosphosulfate | ChEBI | 3'-Phosphonatoadenosine 5'-phosphosulfate tetraanion | ChEBI | 3'-Phosphonatoadenosine 5'-phosphosulfate(4-) | ChEBI | PAPS | ChEBI | PAPS tetraanion | ChEBI | PAPS(4-) | ChEBI | 3'-Phosphoadenylyl sulfuric acid | Generator | 3'-Phosphoadenylyl sulphate | Generator | 3'-Phosphoadenylyl sulphuric acid | Generator | 3'-Phosphonato-5'-adenylyl sulfuric acid | Generator | 3'-Phosphonato-5'-adenylyl sulphate | Generator | 3'-Phosphonato-5'-adenylyl sulphuric acid | Generator | 3'-Phosphonato-5'-adenylyl sulfuric acid tetraanion | Generator | 3'-Phosphonato-5'-adenylyl sulphate tetraanion | Generator | 3'-Phosphonato-5'-adenylyl sulphuric acid tetraanion | Generator | 3'-Phosphonatoadenosine 5'-phosphosulfuric acid | Generator | 3'-Phosphonatoadenosine 5'-phosphosulphate | Generator | 3'-Phosphonatoadenosine 5'-phosphosulphuric acid | Generator | 3'-Phosphonatoadenosine 5'-phosphosulfuric acid tetraanion | Generator | 3'-Phosphonatoadenosine 5'-phosphosulphate tetraanion | Generator | 3'-Phosphonatoadenosine 5'-phosphosulphuric acid tetraanion | Generator | 3'-Phosphonatoadenosine 5'-phosphosulfuric acid(4-) | Generator | 3'-Phosphonatoadenosine 5'-phosphosulphate(4-) | Generator | 3'-Phosphonatoadenosine 5'-phosphosulphuric acid(4-) | Generator | 3'-Phosphonato-5'-adenylyl sulfuric acid(4-) | Generator | 3'-Phosphonato-5'-adenylyl sulphate(4-) | Generator | 3'-Phosphonato-5'-adenylyl sulphuric acid(4-) | Generator | Phosphoadenosine phosphosulfate | MeSH | Phosphosulfate, phosphoadenosine | MeSH | Adenosine-3'-phosphate-5'-phosphosulfate | MeSH | Adenosine 3' phosphate 5' phosphosulfate | MeSH | Phosphoadenosine-5'-phosphosulfuric acid | Generator | Phosphoadenosine-5'-phosphosulphate | Generator | Phosphoadenosine-5'-phosphosulphuric acid | Generator |
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Chemical Formula | C10H11N5O13P2S |
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Average Molecular Weight | 503.23 |
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Monoisotopic Molecular Weight | 502.957124924 |
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IUPAC Name | (2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[(sulfonatooxy)phosphinato]oxy}methyl)oxolan-3-yl phosphate |
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Traditional Name | PAPS |
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CAS Registry Number | Not Available |
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SMILES | [H][C@]1(COP([O-])(=O)OS([O-])(=O)=O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP([O-])([O-])=O |
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InChI Identifier | InChI=1S/C10H15N5O13P2S/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7(27-29(17,18)19)4(26-10)1-25-30(20,21)28-31(22,23)24/h2-4,6-7,10,16H,1H2,(H,20,21)(H2,11,12,13)(H2,17,18,19)(H,22,23,24)/p-4/t4-,6-,7-,10-/m1/s1 |
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InChI Key | GACDQMDRPRGCTN-KQYNXXCUSA-J |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Acyclic diterpenoids |
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Alternative Parents | |
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Substituents | - Acyclic diterpenoid
- Isoprenoid phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Organic anion
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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phosphoadenosine-5'-phosphosulfate,2TMS,isomer #1 | C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O[Si](C)(C)C | 3369.1 | Semi standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TMS,isomer #1 | C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O[Si](C)(C)C | 3868.0 | Standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TMS,isomer #1 | C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O[Si](C)(C)C | 5696.1 | Standard polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TMS,isomer #2 | C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O)[Si](C)(C)C | 3403.0 | Semi standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TMS,isomer #2 | C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O)[Si](C)(C)C | 3988.8 | Standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TMS,isomer #2 | C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O)[Si](C)(C)C | 5582.8 | Standard polar | 33892256 | phosphoadenosine-5'-phosphosulfate,3TMS,isomer #1 | C[Si](C)(C)O[C@@H]1[C@H](OP(=O)([O-])[O-])[C@@H](COP(=O)([O-])OS(=O)(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21 | 3368.1 | Semi standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,3TMS,isomer #1 | C[Si](C)(C)O[C@@H]1[C@H](OP(=O)([O-])[O-])[C@@H](COP(=O)([O-])OS(=O)(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21 | 4058.8 | Standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,3TMS,isomer #1 | C[Si](C)(C)O[C@@H]1[C@H](OP(=O)([O-])[O-])[C@@H](COP(=O)([O-])OS(=O)(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21 | 5132.1 | Standard polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O[Si](C)(C)C(C)(C)C | 3727.9 | Semi standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O[Si](C)(C)C(C)(C)C | 4406.8 | Standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O[Si](C)(C)C(C)(C)C | 5620.2 | Standard polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O)[Si](C)(C)C(C)(C)C | 3771.0 | Semi standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O)[Si](C)(C)C(C)(C)C | 4454.0 | Standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)([O-])OS(=O)(=O)[O-])[C@@H](OP(=O)([O-])[O-])[C@H]1O)[Si](C)(C)C(C)(C)C | 5423.4 | Standard polar | 33892256 | phosphoadenosine-5'-phosphosulfate,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](OP(=O)([O-])[O-])[C@@H](COP(=O)([O-])OS(=O)(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21 | 3872.9 | Semi standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](OP(=O)([O-])[O-])[C@@H](COP(=O)([O-])OS(=O)(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21 | 4758.1 | Standard non polar | 33892256 | phosphoadenosine-5'-phosphosulfate,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](OP(=O)([O-])[O-])[C@@H](COP(=O)([O-])OS(=O)(=O)[O-])O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21 | 5067.4 | Standard polar | 33892256 |
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