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SID26756925

ID: ALA6608

PubChem CID: 32875

Max Phase: Preclinical

Molecular Formula: C27H29NO11

Molecular Weight: 543.53

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3OC1CC(N)C(O)C(C)O1

Standard InChI:  InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10?,13?,15-,17?,22?,27-/m0/s1

Standard InChI Key:  AOJJSUZBOXZQNB-SNFLSGHGSA-N

Molfile:  

     RDKit          2D

 39 43  0  0  1  0  0  0  0  0999 V2000
    4.1250   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1542   -1.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0875   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1917   -1.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6750   -1.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1125   -3.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -2.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9792   -4.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -4.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -3.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6042   -0.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6000   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -0.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6417   -0.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -2.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -1.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8125   -4.4542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667   -2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -0.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9750   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0500   -2.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  6  1  0
  6  8  2  0
  7 10  2  0
  8  1  1  0
  9  2  1  0
 10  4  1  0
 11 13  1  0
 12  5  1  0
 13  6  1  0
 14 22  1  0
 15 14  1  0
 16 11  1  0
 17 14  1  0
 18 17  1  0
 19 18  1  0
 20 15  1  0
 11 21  1  1
 12 22  1  6
 23 18  1  0
 24  4  2  0
 25  3  2  0
 26  7  1  0
 27 21  2  0
 28  8  1  0
 29  9  1  0
 11 30  1  6
 31 19  1  0
 32 10  1  0
 33 26  1  0
 34 21  1  0
 35 34  1  0
 36 20  1  0
 37 32  2  0
 38 37  1  0
 39 33  1  0
  9  5  2  0
  3  7  1  0
 16 12  1  0
 38 26  2  0
 20 19  1  0
M  END

Associated Targets(Human)

MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HTT Tchem Huntingtin (19182 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KMT2A Tchem Histone-lysine N-methyltransferase MLL (17327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NFE2L2 Tchem Nuclear factor erythroid 2-related factor 2 (95332 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TSG101 Tbio Tumor susceptibility gene 101 protein (2874 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
VDR Tclin Vitamin D receptor (26531 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FEN1 Tchem Flap endonuclease 1 (12055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLI Tchem DNA polymerase iota (116820 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLH Tchem DNA polymerase eta (21678 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
POLK Tbio DNA polymerase kappa (8653 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HEK293 (82097 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SN12C (47755 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-N (28205 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H23 (49055 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ACHN (49357 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UO-31 (46270 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-92 (41141 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-539 (44845 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Malme-3M (44254 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-5 (47095 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A498 (42825 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MOLT-4 (49676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-62 (47048 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI/ADR-RES (33767 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-5 (45555 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-8 (47708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-19 (46794 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TK-10 (45540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SR (39847 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW-620 (52400 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KM12 (47707 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H522 (44358 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
M14 (47487 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H322M (45589 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPMI-8226 (44974 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-4 (44535 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BT-549 (31254 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-2 (46422 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-75 (44215 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCC 2998 (41480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-15 (51914 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EKVX (44102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PC-3 (62116 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T47D (39041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H460 (60772 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-62 (47335 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-435 (38290 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAKI-1 (44928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-295 (48000 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IGROV-1 (47897 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Hs-578T (29457 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-257 (46019 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
786-0 (47912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H226 (44470 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HT-29 (80576 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-28 (48833 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RXF 393 (41971 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
COLO 205 (50209 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GMNN Tbio Geminin (128009 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RACGAP1 Tbio Rac GTPase-activating protein 1 (2057 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ATXN2 Tbio Ataxin-2 (54410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
WRN Tbio Werner syndrome ATP-dependent helicase (8824 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CGA Tbio Glycoprotein hormones alpha chain (29278 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ERG Tbio Transcriptional regulator ERG (5589 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNCA Tchem Alpha-synuclein (10960 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RAPGEF3 Tchem Rap guanine nucleotide exchange factor 3 (15528 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BLM Tchem Bloom syndrome protein (4248 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rorc Nuclear receptor ROR-gamma (89407 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Vero (26788 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Pmp22 Peripheral myelin protein 22 (1279 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: 543.53Molecular Weight (Monoisotopic): 543.1741AlogP: 0.00#Rotatable Bonds: 5
Polar Surface Area: 206.07Molecular Species: BASEHBA: 12HBD: 6
#RO5 Violations: 3HBA (Lipinski): 12HBD (Lipinski): 7#RO5 Violations (Lipinski): 3
CX Acidic pKa: 8.00CX Basic pKa: 9.03CX LogP: 0.53CX LogD: 0.10
Aromatic Rings: 2Heavy Atoms: 39QED Weighted: 0.24Np Likeness Score: 1.81

References

1. PubChem BioAssay data set, 
2. PubChem BioAssay data set, 
3. PubChem BioAssay data set, 
4. 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]
5. 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]
6. Pollock, Jonathan and 6 more authors.  2015-09-24  Rational Design of Orthogonal Multipolar Interactions with Fluorine in Protein-Ligand Complexes.  [PMID:26288158]
7. 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]
8. 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]
9. 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]
10. 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]
11. 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):