Basic information
- CAS
120944-03-8- Standard SMILES
CC(=O)OCOC(c1ccc2ccccc2c1)P(=O)(OCOC(C)=O)OCOC(C)=O- InChIKey
UQODAZKXEREJLZ-UHFFFAOYSA-N- Molecular formula
- C20H23O10P
- Average molar mass
- 454.4 g/mol
- Monoisotopic mass
- 454.10288392
Overview
Hydroxy-2-naphthalenyl-methyl phosphonic acid trisacetoxymethylester is an organic phosphonate that is the trisacetoxymethylester derivative of naphthalene substituted hydroxymethylphosphonic acid. It has been found to inhibit insulin receptor tyrosine kinase activity and insulin stimulated glucose oxidation. It has a role as a tyrosine kinase inhibitor. It is a member of naphthalenes, an organic phosphonate and an acetate ester. It is functionally related to a hydroxymethylphosphonic acid.
Names & identifiers
- Preferred name
- Hydroxy-2-naphthalenyl-methyl phosphonic acid trisacetoxymethylester
- IUPAC
- [bis(acetyloxymethoxy)phosphoryl-naphthalen-2-ylmethoxy]methyl acetate
- English name
- HNMPA-(AM)3
- Molecular formula
- C20H23O10P
- Molecular weight
- 454.36
Names & synonyms
HNMPA-(AM(3))CHEBI:75391hydroxy-2-naphthalenyl-methyl phosphonic acid trisacetoxymethylesterRefChem:147118HNMPA-(AM)3120944-03-8[bis(acetyloxymethoxy)phosphoryl-naphthalen-2-ylmethoxy]methyl acetate((((Acetoxymethoxy)(naphthalen-2-yl)methyl)phosphoryl)bis(oxy))bis(methylene) diacetateBio1_000738MolMap_000027CBiol_001963BSPBio_001119
Show more names
HNMPA-(AM)PRO-DRUG IIHYDROXY-2-NAPHTHALENYLMETHYLPHOSPHONIC ACID TRISACETOXYMETHYL ESTERPhosphonic acid, P-[[(acetyloxy)methoxy]-2-naphthalenylmethyl]-, bis[(acetyloxy)methyl] ester
KBioGR_000459KBioSS_000459orb1693606CHEMBL1435748SCHEMBL30490632BCBcMAP01_000216KBio2_000459KBio2_003027
Database identifiers
- CAS
120944-03-8- PubChem CID
Properties
Computed structural properties
- XLogP
- 2.2
- Topological polar surface area
- 124 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 14
- Heavy atoms
- 31
- Formal charge
- 0
- Complexity
- 642
Physicochemical properties
- Boiling point
- 573.1 · 573.1±50.0 °C(Predicted)
- Density
- 1.325 · 1.325±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- 15 mg/ml; · DMF: 15 mg/ml; DMSO: 1 mg/ml; Ethanol: 25 mg/ml; PBS (pH 7.2): 1 mg/ml
- form
- Colorless oil.
- color
- Colorless to light yellow
- InChI
- 1S/C20H23O10P/c1-14(21)25-11-28-20(19-9-8-17-6-4-5-7-18(17)10-19)31(24,29-12-26-15(2)22)30-13-27-16(3)23/h4-10,20H,11-13H2,1-3H3
- InChIKey
- UQODAZKXEREJLZ-UHFFFAOYSA-N
- SMILES
- [P](=O)(OCOC(=O)C)(OCOC(=O)C)C(OCOC(=O)C)c1cc2c(cc1)cccc2
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319
- Precautionary statements
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- WGK 1
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- Storage Class
- 10 - Combustible liquids
- Hazard statements
- H225-H319
- Precautionary statements
- P210-P233-P240-P241-P242-P243-P264-P280-P303+P361+P353-P305+P351+P338-P337+P313-P370+P378-P403+P235-P501
Chemistry & industry
Applications
UsesHNMPA-(AM)3 is a cell-permeable and selective insulin receptor tyrosine kinase inhibitor analog of HNMPA. HNMPA-(AM)3 greatly inhibits the ability of prothoracicotropic hormone (PTTH) to activate ERK phosphorylation and stimulate ecdysteroidogenesis. HNMPA-(AM)3 is also effective in inhibiting ecdysteroid production (IC50=14.2 μM) and insulin receptor activity (IC50 is 14.2 μM and 200 μM in mosquitoes and mammals, respectively)[1][2].
Suppliers6 total
Aladdin Scientific[email protected]
銳迪國際科技有限公司18024082417 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
TargetMol中国（陶术生物）4008200310 15002144251 · [email protected]
上海阿摩尔生物科技有限公司13370042665 18916960931 · [email protected]
Additional notes
DefinitionChEBI: Hydroxy-2-naphthalenyl-methyl phosphonic acid trisacetoxymethylester is an organic phosphonate that is the trisacetoxymethylester derivative of naphthalene substituted hydroxymethylphosphonic acid. It has been found to inhibit insulin receptor tyrosine kinase activity and insulin stimulated glucose oxidation. It has a role as a tyrosine kinase inhibitor. It is an organic phosphonate, a member of naphthalenes and an acetate ester. It is functionally related to a hydroxymethylphosphonic acid.
Related reactions
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Compound notes
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