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SID11110764

ID: ALA156

Cas Number: 51865-79-3

PubChem CID: 72440

Max Phase: Preclinical

Molecular Formula: C20H22N8O5

Molecular Weight: 454.45

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@H](CCC(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C20H22N8O5/c1-28(9-11-8-23-17-15(24-11)16(21)26-20(22)27-17)12-4-2-10(3-5-12)18(31)25-13(19(32)33)6-7-14(29)30/h2-5,8,13H,6-7,9H2,1H3,(H,25,31)(H,29,30)(H,32,33)(H4,21,22,23,26,27)/t13-/m1/s1

Standard InChI Key:  FBOZXECLQNJBKD-CYBMUJFWSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  1  0  0  0  0  0999 V2000
    1.3917   -1.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -0.8625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4375   -1.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -1.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9250   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -2.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6375   -2.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417   -0.8417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6417   -3.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -1.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1792   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -1.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1667   -3.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -2.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0125   -2.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7250   -3.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -2.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1500   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7125   -4.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -1.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7125   -2.8542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -2.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5875   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -2.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5667   -1.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8625   -0.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6792   -3.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2125   -3.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -4.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2542   -3.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -1.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  5  2  0
  4  2  2  0
  5  1  1  0
  6  1  2  0
  7  3  1  0
  8 15  1  0
  9  4  1  0
 10  8  1  0
 11  7  2  0
 14 12  1  6
 13 16  1  0
 14 10  1  0
 15 25  1  0
 16 11  1  0
 17 30  1  0
 18 13  1  0
 19  8  2  0
 20 12  2  0
 21  9  2  0
 22 17  2  0
 23  5  1  0
 24 26  1  0
 25 27  2  0
 26 18  2  0
 27 18  1  0
 28  6  1  0
 29 14  1  0
 30 29  1  0
 31 12  1  0
 32 17  1  0
 33 13  1  0
  4  3  1  0
 21 11  1  0
 15 24  2  0
M  END

Alternative Forms

  1. Parent:

Associated Targets(Human)

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LMNA Tbio Prelamin-A/C (36751 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMN1 Tchem Survival motor neuron protein (34246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HPGD Tchem 15-hydroxyprostaglandin dehydrogenase [NAD+] (24926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TP53 Tchem Cellular tumor antigen p53 (48468 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATXN2 Tbio Ataxin-2 (54410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FTL Ferritin light chain (43324 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Abcc2 Canalicular multispecific organic anion transporter 1 (241 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

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

Calculated Properties

Molecular Weight: 454.45Molecular Weight (Monoisotopic): 454.1713AlogP: 0.27#Rotatable Bonds: 9
Polar Surface Area: 210.54Molecular Species: ACIDHBA: 10HBD: 5
#RO5 Violations: HBA (Lipinski): 13HBD (Lipinski): 7#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.25CX Basic pKa: 2.80CX LogP: -0.24CX LogD: -6.56
Aromatic Rings: 3Heavy Atoms: 33QED Weighted: 0.29Np Likeness Score: -0.53

References

1. PubChem BioAssay data set, 
2. PubChem BioAssay data set, 
3. PubChem BioAssay data set, 
4. Masuda M, I'izuka Y, Yamazaki M, Nishigaki R, Kato Y, Ni'inuma K, Suzuki H, Sugiyama Y..  (1997)  Methotrexate is excreted into the bile by canalicular multispecific organic anion transporter in rats.,  57  (1): [PMID:9270020]
5. 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]
6. 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]
7. Pollock, Jonathan and 6 more authors.  2015-09-24  Rational Design of Orthogonal Multipolar Interactions with Fluorine in Protein-Ligand Complexes.  [PMID:26288158]
8. 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]
9. 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]
10. 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]
11. 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]
12. 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]