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methyl (2S)-2-[[(4-bromophenoxy)-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]amino]propanoate

HCID 5481102
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Basic information

CAS
217178-62-6
Standard SMILES
COC(=O)[C@H](C)NP(=O)(OC[C@@H]1C=C[C@H](n2cc(C)c(=O)[nH]c2=O)O1)Oc1ccc(Br)cc1
InChIKey
VPABMVYNSQRPBD-MIOXLMGNSA-N
Molecular formula
C20H23BrN3O8P
Average molar mass
544.3 g/mol
Monoisotopic mass
543.04061

Names & identifiers

Preferred name
methyl (2S)-2-[[(4-bromophenoxy)-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]amino]propanoate
IUPAC
methyl (2S)-2-[[(4-bromophenoxy)-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]amino]propanoate
English name
Stampidine
Molecular formula
C20H23BrN3O8P
Molecular weight
544.29

Names & synonyms

methyl (2S)-2-[[(4-bromophenoxy)-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]amino]propanoateorb1702764CHEMBL5196951SCHEMBL26308929AKOS040746382methyl (2S)-2-[[(4-bromophenoxy)-[[(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]phosphoryl]amino]propanoateHY-122470CS-0085672G17915T24839HI 113Sampidine
Show more names
Stampidine

Database identifiers

CAS
217178-62-6
PubChem CID
5481102
ChEMBL
CHEMBL5196951
Nikkaji
J1.575.378A

Properties

Computed structural properties

XLogP
1.7
Topological polar surface area
133 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
9
Rotatable bonds
10
Heavy atoms
33
Formal charge
0
Complexity
873

Physicochemical properties

Melting point
59 °C · 59 °C
Density
1.515 · 1.515±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
storage temp.
-20 °C · Store at -20°C
solubility
100 mg/mL · DMSO : 100 mg/mL (183.73 mM; Need ultrasonic)
form
Solid
pka
9.548 · 9.548±0.10(predicted)
color
White to off-white
FDA UNII
9 I3MQ1X · MHN9I3MQ1X

Chemistry & industry

Applications · 1 item

UsesStampidine is a nucleoside reverse transcriptase inhibitor (NRTI) with potent and broad-spectrum anti-HIV activity. Stampidine inhibits the laboratory HIV-1 strain HTLVIIIB (B-envelope subtype) and primary clinical isolates with IC50s of 1 nM and 2 nM, respectively. Stampidine also inhibits NRTI-resistant primary clinical isolates and NNRTI-resistant clinical isolates with IC50s of 8.7 nM and 11.2 nM, respectively[1].

Suppliers11 total

浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
銳迪國際科技有限公司18024082417 · [email protected]
杭州六可生物科技有限公司+86-571-86912261 19975279805 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)4008200310 15002144251 · [email protected]
上海陌孚医药科技有限公司4000862158 18117107507 · [email protected]
上海一飞生物科技有限公司021-65675885 18964387627 · [email protected]
上海梅凯科技有限公司15300790979 18964014359 · [email protected]
AFINE CHEMICALS LIMITED+86-571-85134551 +86-18958018566 · [email protected]

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