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SID50112891

ID: ALA34668

PubChem CID: 24868306

Max Phase: Preclinical

Molecular Formula: C16H16NO6P

Molecular Weight: 349.28

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Synonyms: CGS-35066 | 3-dibenzofuran-3-yl-2-(phosphonomethylamino)propanoic acid|3-dibenzofuran-3-yl-2-(phosphonomethylamino)propionic acid|CHEMBL34668|SCHEMBL4558321|HMS3742E15|NCGC00167755-01

Canonical SMILES:  O=C(O)C(Cc1ccc2c(c1)oc1ccccc12)NCP(=O)(O)O

Standard InChI:  InChI=1S/C16H16NO6P/c18-16(19)13(17-9-24(20,21)22)7-10-5-6-12-11-3-1-2-4-14(11)23-15(12)8-10/h1-6,8,13,17H,7,9H2,(H,18,19)(H2,20,21,22)

Standard InChI Key:  CRUVAUSVWLATAE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    4.6792   -4.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -2.3750    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.4667   -3.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6875   -4.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4750   -5.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1167   -2.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8292   -2.3750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -5.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6917   -1.5875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2625   -4.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5500   -3.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2667   -1.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -1.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0625   -3.0417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2542   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9792   -2.7875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8125   -5.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -5.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -5.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  8  1  0
  3  1  1  0
  4  1  1  0
  5  4  1  0
  6  3  1  0
  7 10  1  0
  8  9  1  0
  9 10  1  0
 10 15  1  0
 11  4  2  0
 12  1  2  0
 13  2  2  0
 14 12  1  0
 15 14  1  0
 16  7  2  0
 17  2  1  0
 18  2  1  0
 19 14  2  0
 20  7  1  0
 21  5  1  0
 22  6  1  0
 23 21  2  0
 24 22  2  0
  5  6  2  0
 19 11  1  0
 24 23  1  0
M  END

Associated Targets(Human)

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

FTL Ferritin light chain (43324 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Calculated Properties

Molecular Weight: 349.28Molecular Weight (Monoisotopic): 349.0715AlogP: 2.31#Rotatable Bonds: 6
Polar Surface Area: 120.00Molecular Species: ACIDHBA: 4HBD: 4
#RO5 Violations: HBA (Lipinski): 7HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: -0.57CX Basic pKa: 6.19CX LogP: 0.46CX LogD: -3.27
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.50Np Likeness Score: 0.23

References

1. PubChem BioAssay data set, 
2. Zhou, Haibin H and 7 more authors.  2013-02-14  Structure-based design of high-affinity macrocyclic peptidomimetics to block the menin-mixed lineage leukemia 1 (MLL1) protein-protein interaction.  [PMID:23244744]
3. He, Shihan S and 10 more authors.  2014-02-27  High-affinity small-molecule inhibitors of the menin-mixed lineage leukemia (MLL) interaction closely mimic a natural protein-protein interaction.  [PMID:24472025]
4. Pollock, Jonathan and 6 more authors.  2015-09-24  Rational Design of Orthogonal Multipolar Interactions with Fluorine in Protein-Ligand Complexes.  [PMID:26288158]
5. Borkin, Dmitry D and 12 more authors.  2016-02-11  Property Focused Structure-Based Optimization of Small Molecule Inhibitors of the Protein-Protein Interaction between Menin and Mixed Lineage Leukemia (MLL).  [PMID:26744767]
6. Borkin, Dmitry D and 12 more authors.  2018-06-14  Complexity of Blocking Bivalent Protein-Protein Interactions: Development of a Highly Potent Inhibitor of the Menin-Mixed-Lineage Leukemia Interaction.  [PMID:29738674]
7. Chen, Qi-Bin QB, Gao, Jie J, Zou, Guo-An GA, Xin, Xue-Lei XL and Aisa, Haji Akber HA.  2018-06-22  Piperidine Alkaloids with Diverse Skeletons from Anacyclus pyrethrum.  [PMID:29775308]
8. Aguilar, Angelo A and 15 more authors.  2019-07-11  Structure-Based Discovery of M-89 as a Highly Potent Inhibitor of the Menin-Mixed Lineage Leukemia (Menin-MLL) Protein-Protein Interaction.  [PMID:31244110]
9. Xu, Shilin and 12 more authors.  2020-05-14  Discovery of M-808 as a Highly Potent, Covalent, Small-Molecule Inhibitor of the Menin-MLL Interaction with Strong In Vivo Antitumor Activity.  [PMID:32338903]

Source

Source(1):