Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-10-08 08:37:25 UTC |
---|
Updated at | 2022-10-08 08:50:49 UTC |
---|
NP-MRD ID | NP0331092 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Pamoic acid |
---|
Description | Pamoic acid, also known as pamoate or pamosaeure, belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. Pamoic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Salts and esters of pamoic acid are known as pamoates or embonates. Hydrogen bonds facilitate the dissolution of compounds in water. The presence of multiple oxygen atoms enables significant hydrogen bonding to occur. Pamoic acid has agonist activity for the orphan G protein-coupled receptor GPR35 by which it activates ERK and beta-arrestin2, and causes antinociceptive activity. Pamoic acid, also called embonic acid, is a naphthoic acid derivative. It can be prepared by the reaction of 2-hydroxy-3-naphthoic acid with formaldehyde. In pharmacology, the salt form of pamoic acid (pamoate ion) can be used as a counterion of a drug compound to affect the dissolution rate of the drug. It was first documented in 2008 (PMID: 18416825). Pharmaceutical drugs formulated this way include cycloguanil pamoate, hydroxyzine pamoate, imipramine pamoate, olanzapine pamoate hydrate, oxantel pamoate, pyrantel pamoate, and pyrvinium pamoate (PMID: 36071400). |
---|
Structure | OC(=O)C1=CC2=CC=CC=C2C(CC2=C(O)C(=CC3=CC=CC=C23)C(O)=O)=C1O InChI=1S/C23H16O6/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29/h1-10,24-25H,11H2,(H,26,27)(H,28,29) |
---|
Synonyms | Value | Source |
---|
4,4'-Methylen-bis-(3-hydroxy-2-naphthoesaeure) | ChEBI | 4,4'-Methylenebis(3-hydroxy-2-naphthoic acid) | ChEBI | Embonic acid | ChEBI | Pamosaeure | ChEBI | 4,4'-Methylenebis(3-hydroxy-2-naphthoate) | Generator | Embonate | Generator | Pamoate | Generator | Pamoic acid, disodium salt | MeSH | 4,4'-Methylenebis(3-hydroxy)-2-naphthoic acid naphthalenecarboxylic acid | MeSH | Pamoic acid, dirubidium salt | MeSH | Pamoic acid, dilithium salt | MeSH | Pamoic acid, dicesium salt | MeSH | Pamoic acid, dipotassium salt | MeSH | Sodium pamoate | MeSH | 4-[(3-Carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylate | Generator | Pamoic acid | MeSH |
|
---|
Chemical Formula | C23H28N2O4 |
---|
Average Mass | 396.4870 Da |
---|
Monoisotopic Mass | 396.20491 Da |
---|
IUPAC Name | 4-[(3-carboxy-2-hydroxynaphthalen-1-yl)methyl]-3-hydroxynaphthalene-2-carboxylic acid |
---|
Traditional Name | pamoic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | CO\C=C(/[C@H]1C[C@H]2N(CCC3=C2NC2=CC=CC(OC)=C32)C[C@@H]1C=C)C(=O)OC |
---|
InChI Identifier | InChI=1S/C23H28N2O4/c1-5-14-12-25-10-9-15-21-18(7-6-8-20(21)28-3)24-22(15)19(25)11-16(14)17(13-27-2)23(26)29-4/h5-8,13-14,16,19,24H,1,9-12H2,2-4H3/b17-13+/t14-,16-,19+/m0/s1 |
---|
InChI Key | JGZKIGWXPPFMRG-CGJCNEAHSA-N |
---|
Experimental Spectra |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO, simulated) | Xinyan_8339 | | | 2022-10-08 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO, experimental) | Xinyan_8339 | | | 2022-10-08 | View Spectrum |
| Predicted Spectra |
---|
|
| Not Available | Chemical Shift Submissions |
---|
|
| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 400 MHz, DMSO, simulated) | xinyan_8339@126.com | Not Available | Not Available | 2022-10-08 | View Spectrum |
| Species |
---|
Species of Origin | Not Available |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as naphthalenecarboxylic acids. Naphthalenecarboxylic acids are compounds containing a naphthalene moiety, which bears a carboxylic acid group one or more positions. Naphthalene is a bicyclic compound that is made up of two fused benzene ring. |
---|
Kingdom | Organic compounds |
---|
Super Class | Benzenoids |
---|
Class | Naphthalenes |
---|
Sub Class | Naphthalenecarboxylic acids and derivatives |
---|
Direct Parent | Naphthalenecarboxylic acids |
---|
Alternative Parents | |
---|
Substituents | - 2-naphthalenecarboxylic acid
- 2-naphthol
- Salicylic acid or derivatives
- Hydroxybenzoic acid
- Dicarboxylic acid or derivatives
- Vinylogous acid
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homopolycyclic compound
|
---|
Molecular Framework | Aromatic homopolycyclic compounds |
---|
External Descriptors | |
---|
Physical Properties |
---|
State | Not Available |
---|
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 | |
---|
General References | - De Leo F, Rossi A, De Marchis F, Cigana C, Melessike M, Quilici G, De Fino I, Mantonico MV, Fabris C, Bragonzi A, Bianchi ME, Musco G: Pamoic acid is an inhibitor of HMGB1.CXCL12 elicited chemotaxis and reduces inflammation in murine models of Pseudomonas aeruginosa pneumonia. Mol Med. 2022 Sep 7;28(1):108. doi: 10.1186/s10020-022-00535-z. [PubMed:36071400 ]
- Hazan C, Boudsocq F, Gervais V, Saurel O, Ciais M, Cazaux C, Czaplicki J, Milon A: Structural insights on the pamoic acid and the 8 kDa domain of DNA polymerase beta complex: towards the design of higher-affinity inhibitors. BMC Struct Biol. 2008 Apr 16;8:22. doi: 10.1186/1472-6807-8-22. [PubMed:18416825 ]
|
---|