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SID11111041

ID: ALA36622

Max Phase: Preclinical

Molecular Formula: C19H23NO5

Molecular Weight: 345.40

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cccc(OC)c1OCCNC[C@@H]1COc2ccccc2O1

Standard InChI:  InChI=1S/C19H23NO5/c1-21-17-8-5-9-18(22-2)19(17)23-11-10-20-12-14-13-24-15-6-3-4-7-16(15)25-14/h3-9,14,20H,10-13H2,1-2H3/t14-/m1/s1

Standard InChI Key:  GYSZUJHYXCZAKI-CQSZACIVSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.7464    1.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7453    0.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4596   -0.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4579    1.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1728    1.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1760    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8947   -0.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6149    0.3710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6117    1.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8883    1.6196    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3250    1.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0406    1.2078    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7539    1.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4696    1.2119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1828    1.6265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8985    1.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8958    0.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6107   -0.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3250    0.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3199    1.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6045    1.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5980    2.4572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1812   -0.0202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1809   -0.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3092    2.8753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  1  2  2  0
 12 13  1  0
 13 14  1  0
  2  3  1  0
 14 15  1  0
  3  6  2  0
 15 16  1  0
 16 17  2  0
  5  4  2  0
 17 18  1  0
  5 10  1  0
 18 19  2  0
  6  7  1  0
 19 20  1  0
  7  8  1  0
 20 21  2  0
 21 16  1  0
  8  9  1  0
 21 22  1  0
  9 10  1  0
 17 23  1  0
  4  1  1  0
 23 24  1  0
  9 11  1  6
 22 25  1  0
  5  6  1  0
M  END

Alternative Forms

Associated Targets(Human)

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THPO Tbio Thrombopoietin (834 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ALOX15B Tchem Arachidonate 15-lipoxygenase, type II (7244 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1D Tclin Alpha-1d adrenergic receptor (4171 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTR1A Tclin Serotonin 1a (5-HT1a) receptor (14969 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ADRA1B Tclin Alpha-1b adrenergic receptor (2912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Chrm1 Muscarinic acetylcholine receptor M1 (3437 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: 345.40Molecular Weight (Monoisotopic): 345.1576AlogP: 2.51#Rotatable Bonds: 8
Polar Surface Area: 58.18Molecular Species: BASEHBA: 6HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: CX Basic pKa: 8.76CX LogP: 2.51CX LogD: 1.14
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.74Np Likeness Score: -0.20

References

1. PubChem BioAssay data set, 
2. PubChem BioAssay data set, 
3. Bonifazi A, Piergentili A, Del Bello F, Farande Y, Giannella M, Pigini M, Amantini C, Nabissi M, Farfariello V, Santoni G, Poggesi E, Leonardi A, Menegon S, Quaglia W..  (2013)  Structure-activity relationships in 1,4-benzodioxan-related compounds. 11. (1) reversed enantioselectivity of 1,4-dioxane derivatives in α1-adrenergic and 5-HT1A receptor binding sites recognition.,  56  (2): [PMID:23252794] [10.1021/jm301525w]
4. PubChem BioAssay data set, 
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]