General Information of the Compound
Compound ID
CP0048821
Compound Name
(R,S)-2-phosphonomethylpentanedioic acid
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Synonyms
173039-10-6
2-(PHOSPHONOMETHYL)-PENTANEDIOIC ACID
2-(Phosphonomethyl)pentanedioic acid
2-(phosphonomethyl)pentanedioic acid
2-PMPA
2-PMPA(NAALADaseinhibitor)
2-PMPA, &gt
2-Phosphonomethyl-pentanedioic acid
AKOS016004257
ANW-62579
API0001123
BDBM17659
CHEMBL47009
CS-6202
CTK0E4395
DTXSID90436036
EX-A1248
HMS3267D10
ISEYJGQFXSTPMQ-UHFFFAOYSA-N
KS-00001CPM
MP-2042
MolPort-023-276-085
PMPA (NAALADase inhibitor)
PMPA(NAALADaseinhibitor)
Pentanedioic acid, 2-(phosphonomethyl)-
SCHEMBL383173
pentanedioic acid analogue, (RS)-1
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Structure
Formula
C6H11O7P
Molecular Weight
226.121
Canonical SMILES
OC(=O)CCC(CP(O)(O)=O)C(O)=O
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InChI
InChI=1S/C6H11O7P/c7-5(8)2-1-4(6(9)10)3-14(11,12)13/h4H,1-3H2,(H,7,8)(H,9,10)(H2,11,12,13)
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InChIKey
ISEYJGQFXSTPMQ-UHFFFAOYSA-N
Physicochemical Property
logP
-0.2703
Rotatable Bonds
6
Heavy Atom Count
14
Polar Areas
132.13
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
3
Complexity
14

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 10130754
SID: 15121544
ChEMBL ID
CHEMBL47009
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT02647, Glutamate carboxypeptidase 2
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000141 LNCaP
 Cell Line Info 
Homo sapiens (Human)  5
1
IC50 = 1.1 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
IC50 = 52 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
Kd = 0.4 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
4
Ki = 0.4 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
5
Ki = 31.2 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000048 PC-3
 Cell Line Info 
Homo sapiens (Human)  1
1
Kd = 0.5 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 EC50 = 0.62 nM
2 IC50 = 0.3 nM
3 IC50 = 80 nM
4 Ki = 0.2 nM
5 Ki = 0.28 nM
6 Ki = 0.3 nM
Clinical Information about the Compound
Drug 1 ( 2-PMPA )
Drug Name 2-PMPA
Target(s)
Glutamate carboxypeptidase II (GCPII)
 Target Info 
Inhibitor