(3S,4R,5Z,8S,9S,11E)-14-(2-(1H-imidazol-1-yl)ethylamino)-8,9,16-trihydroxy-3,4-dimethyl-3,4,9,10-tetrahydro-1H-benzo[c][1]oxacyclotetradecine-1,7(8H)-dione

ID: ALA3986872

PubChem CID: 57624674

Max Phase: Preclinical

Molecular Formula: C24H29N3O6

Molecular Weight: 455.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@H]1/C=C\C(=O)[C@@H](O)[C@@H](O)C/C=C/c2cc(NCCn3ccnc3)cc(O)c2C(=O)O[C@H]1C

Standard InChI:  InChI=1S/C24H29N3O6/c1-15-6-7-20(29)23(31)19(28)5-3-4-17-12-18(26-9-11-27-10-8-25-14-27)13-21(30)22(17)24(32)33-16(15)2/h3-4,6-8,10,12-16,19,23,26,28,30-31H,5,9,11H2,1-2H3/b4-3+,7-6-/t15-,16+,19+,23+/m1/s1

Standard InChI Key:  LMYOWCIKBBBUHZ-XSVIZIDSSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    9.4129   -7.4566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1821   -7.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1699   -6.2360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5187   -5.7475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6742   -5.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0307   -6.2612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3687   -5.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6550   -6.2032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7247   -7.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4823   -7.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374   -8.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8689   -8.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9229   -8.6694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4293   -8.2275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1471   -8.6401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1355   -9.4672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0524   -7.4995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3037   -7.1536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2278   -6.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9019   -5.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9019   -5.0300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5857   -7.5663    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5857   -8.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8720   -8.8043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3687   -4.9652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6438   -4.9032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7313   -4.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6992   -7.0440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1623   -8.3951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0716   -7.5775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2702   -7.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8609   -8.1175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4096   -8.7259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  6  1  0
  8  7  1  0
  8  9  2  0
 10  9  1  0
 11 10  2  0
 12 11  1  0
 12 13  1  0
 14 13  1  0
  1 14  1  0
 14 15  1  1
 13 16  1  1
  9 17  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
  8 20  1  0
 20 21  1  0
 18 22  1  0
 22 23  1  0
 23 24  1  0
  7 25  2  0
  5 26  1  1
  4 27  1  6
  1 28  2  0
 24 29  1  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3986872

   (4S,5R,6Z,9S,10S,12E)-9,10,18-trihydroxy-16-(2-imidazol-1-ylethylamino)-4,5-dimethyl-3-oxabicyclo[12.4.0]octadeca-1(14),6,12,15,17-pentaene-2,8-dione

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 455.51

Molecular Weight (Monoisotopic): 455.2056

AlogP: 2.15

#Rotatable Bonds: 4

Polar Surface Area: 133.91

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: 6.51

CX LogP: 2.47

CX LogD: 2.43

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.52

Np Likeness Score: 0.95

References

1.  (2009)  Multikinase inhibitors for use in the treatment of cancer, 

Source

Source(1):

• Patent Bioactivity Data