2-Amino-4-phosphono-butyric acid (AP4)

ID: ALA285843

Cas Number: 20263-07-4

PubChem CID: 2207

Product Number: X168370, Order Now?

Max Phase: Preclinical

Molecular Formula: C4H10NO5P

Molecular Weight: 183.10

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CCP(=O)(O)O)C(=O)O

Standard InChI:  InChI=1S/C4H10NO5P/c5-3(4(6)7)1-2-11(8,9)10/h3H,1-2,5H2,(H,6,7)(H2,8,9,10)

Standard InChI Key:  DDOQBQRIEWHWBT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 11 10  0  0  0  0  0  0  0  0999 V2000
   -0.2458   -6.6292    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7083   -5.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3875   -7.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9833   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8333   -6.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5583   -5.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750   -4.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3375   -6.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1083   -6.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2750   -5.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9833   -6.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  2  0
  4  5  1  0
  5  1  1  0
  6  4  1  0
  7  2  2  0
  8  1  1  0
  9  1  1  0
 10  2  1  0
 11  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA285843

   (±)-2-Amino-4-phosphonobutyric acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 183.10

Molecular Weight (Monoisotopic): 183.0297

AlogP: -1.03

#Rotatable Bonds: 4

Polar Surface Area: 120.85

Molecular Species: ZWITTERION

HBA: 3

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.62

CX Basic pKa: 9.57

CX LogP: -3.73

CX LogD: -7.04

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.41

Np Likeness Score: 1.12

References

1. Ortwine DF, Malone TC, Bigge CF, Drummond JT, Humblet C, Johnson G, Pinter GW..  (1992)  Generation of N-methyl-D-aspartate agonist and competitive antagonist pharmacophore models. Design and synthesis of phosphonoalkyl-substituted tetrahydroisoquinolines as novel antagonists.,  35  (8): [PMID:1533422] [10.1021/jm00086a004]

2. Kozikowski AP, Steensma D, Araldi GL, Tückmantel W, Wang S, Pshenichkin S, Surina E, Wroblewski JT..  (1998)  Synthesis and biology of the conformationally restricted ACPD analogue, 2-aminobicyclo[2.1.1]hexane-2,5-dicarboxylic acid-I, a potent mGluR agonist.,  41  (10): [PMID:9572889] [10.1021/jm970719q]

3. Chittur S, Griffith R..  (2002)  Multisubstrate analogue inhibitors of glucosamine-6-phosphate synthase from Candida albicans.,  12  (18): [PMID:12182877] [10.1016/s0960-894x(02)00510-3]

4. Tuckmantel W, Kozikowski AP, Shaomeng Wang, Pshenichkin S, Wroblewski JT.  (1997)  Synthesis, molecular modeling, and biology of the 1-benzyl derivative of APDC-an apparent mGluR6 selective ligand,  7  (5): [10.1016/S0960-894X(97)00068-1]

5. Wheeler WJ, Clodfelter DK, Collado I, Kulanthaivel P, Pedregal C, Stoddard EA, Wright RA, Schoepp DD..  (2005)  (2S,1'S,2'R,3'R)-2(2'-Carboxy-3'-hydroxymethylcyclopropyl)glycine-[3H], a potent and selective radioligand for labeling group 2 and 3 metabotropic glutamate receptors.,  15  (2): [PMID:15603952] [10.1016/j.bmcl.2004.10.093]

6. Diamandis P, Wildenhain J, Clarke ID, Sacher AG, Graham J, Bellows DS, Ling EK, Ward RJ, Jamieson LG, Tyers M, Dirks PB..  (2007)  Chemical genetics reveals a complex functional ground state of neural stem cells.,  3  (5): [PMID:17417631] [10.1038/nchembio873]

7. PubChem BioAssay data set, 

8. PubChem BioAssay data set, 

9. PubChem BioAssay data set, 

10. PubChem BioAssay data set, 

11. PubChem BioAssay data set, 

12. Pal M, Bearne SL..  (2014)  Inhibition of glutamate racemase by substrate-product analogues.,  24  (5): [PMID:24507924] [10.1016/j.bmcl.2013.12.114]

13. PubChem BioAssay data set, 

14.  (2021)  EUbOPEN Chemogenomics Library wave 1,  [10.6019/CHEMBL4689842]

15. EUbOPEN.  (2022)  EUbOPEN Chemogenomics Library wave 2 - DSF,  [10.6019/CHEMBL5060014]

16. EUbOPEN.  (2023)  GPCR results for EUbOPEN Chemogenomics Library 3,  [10.6019/CHEMBL5209801]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• EUbOPEN Chemogenomic Library