7-Amino-2-[1-(4-hydroxy-3,5-dimethyl-phenyl)-meth-(E)-ylidene]-5,6-dimethoxy-indan-1-one

ID: ALA144647

PubChem CID: 5470230

Max Phase: Preclinical

Molecular Formula: C20H21NO4

Molecular Weight: 339.39

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(N)c1OC)C(=O)/C(=C/c1cc(C)c(O)c(C)c1)C2

Standard InChI:  InChI=1S/C20H21NO4/c1-10-5-12(6-11(2)18(10)22)7-14-8-13-9-15(24-3)20(25-4)17(21)16(13)19(14)23/h5-7,9,22H,8,21H2,1-4H3/b14-7+

Standard InChI Key:  KJTPWUVVLPCPJD-VGOFMYFVSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    5.5542   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -5.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -6.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -6.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -5.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5417   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3417   -5.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6917   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2625   -5.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -5.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -4.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6875   -5.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2542   -5.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -6.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917   -7.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8417   -7.5125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -6.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4167   -5.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4042   -4.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -6.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -3.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -6.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000   -5.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  1  2  0
  4  1  1  0
  5  1  1  0
  6  3  1  0
  7  2  2  0
  8 12  1  0
  9  5  1  0
 10 14  2  0
 11  7  1  0
 12  5  2  0
 13 15  2  0
 14 16  1  0
 15 11  1  0
 16 11  2  0
 17  4  2  0
 18  3  1  0
 19  6  1  0
 20  8  1  0
 21 10  1  0
 22 14  1  0
 23 13  1  0
 24 19  1  0
 25 20  1  0
  2  9  1  0
  6  8  2  0
 13 10  1  0
M  END

Alternative Forms

  1. Parent:

    ALA144647

    Indanocine

Associated Targets(Human)

Jurkat (10389 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MOLT-4 (49676 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
WIL2 (182 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
WI-38 (2654 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
K562 (73714 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL-60 (67320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H596 (325 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI-H292 (733 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A549 (127892 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
SF-539 (44845 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DU-145 (51482 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-5 (47095 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-3 (48710 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
A498 (42825 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HOP-62 (47048 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI/ADR-RES (33767 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
U-251 (51189 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-8 (47708 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
OVCAR-5 (45555 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SNB-19 (46794 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-231 (73002 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SR (39847 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TK-10 (45540 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SW-620 (52400 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
KM12 (47707 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
LOX IMVI (44321 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SK-MEL-2 (46422 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
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCT-116 (91556 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
SK-OV-3 (52876 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T47D (39041 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
CAKI-1 (44928 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MDA-MB-435 (38290 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
786-0 (47912 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
UACC-257 (46019 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
MES-SA/Dx5 (643 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HL60/ADR (13 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KB 3-1 (1143 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

L1210 (27553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
B16 (5829 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NIH3T3 (5395 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
TUBB2B Tubulin (2175 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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 339.39Molecular Weight (Monoisotopic): 339.1471AlogP: 3.43#Rotatable Bonds: 3
Polar Surface Area: 81.78Molecular Species: NEUTRALHBA: 5HBD: 2
#RO5 Violations: HBA (Lipinski): 5HBD (Lipinski): 3#RO5 Violations (Lipinski):
CX Acidic pKa: 9.73CX Basic pKa: 2.33CX LogP: 4.12CX LogD: 4.12
Aromatic Rings: 2Heavy Atoms: 25QED Weighted: 0.66Np Likeness Score: 0.52

References

1. Shih H, Deng L, Carrera CJ, Adachi S, Cottam HB, Carson DA..  (2000)  Rational design, synthesis and structure-activity relationships of antitumor (E)-2-benzylidene-1-tetralones and (E)-2-benzylidene-1-indanones.,  10  (5): [PMID:10743954] [10.1016/s0960-894x(00)00032-9]
2. PubChem BioAssay data set, 
3. Da C, Mooberry SL, Gupton JT, Kellogg GE..  (2013)  How to deal with low-resolution target structures: using SAR, ensemble docking, hydropathic analysis, and 3D-QSAR to definitively map the αβ-tubulin colchicine site.,  56  (18): [PMID:23961916] [10.1021/jm400954h]
4. Lazinski LM, Royal G, Robin M, Maresca M, Haudecoeur R..  (2022)  Bioactive Aurones, Indanones, and Other Hemiindigoid Scaffolds: Medicinal Chemistry and Photopharmacology Perspectives.,  65  (19.0): [PMID:36126323] [10.1021/acs.jmedchem.2c01150]