(R)-1-((4-((4-fluoro-2-(hydroxymethyl)-1H-indol-5-yl)oxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl)oxy)propan-2-ol

ID: ALA3526621

PubChem CID: 51352972

Max Phase: Preclinical

Molecular Formula: C19H19FN4O4

Molecular Weight: 386.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c(OC[C@@H](C)O)cn2ncnc(Oc3ccc4[nH]c(CO)cc4c3F)c12

Standard InChI:  InChI=1S/C19H19FN4O4/c1-10(26)8-27-16-6-24-18(11(16)2)19(21-9-22-24)28-15-4-3-14-13(17(15)20)5-12(7-25)23-14/h3-6,9-10,23,25-26H,7-8H2,1-2H3/t10-/m1/s1

Standard InChI Key:  NRYXTTFKQXSWLA-SNVBAGLBSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.5689   -6.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5677   -7.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2825   -7.7729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2807   -6.1200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9960   -6.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9963   -7.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7866   -7.6166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2750   -6.9442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7862   -6.2721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2827   -8.5977    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.0998   -6.9439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8530   -7.7718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8524   -8.5968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8511  -10.2451    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5682   -9.8288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5657   -9.0060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1365   -9.8312    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380   -9.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3506   -8.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625   -9.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3483  -10.0858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971   -7.9606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0376   -9.4135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6263   -8.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8014   -8.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3903   -7.9818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3877   -9.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5126   -7.6581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  3 10  1  0
  8 11  1  0
  2 12  1  0
 12 13  1  0
 13 18  1  0
 17 14  1  0
 14 15  2  0
 15 16  1  0
 16 13  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 17  1  0
 19 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  6
 11 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3526621

   (2R)-1-[4-[[4-fluoro-2-(hydroxymethyl)-1H-indol-5-yl]oxy]-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl]oxypropan-2-ol

2. Alternative Forms:

   

   ALA3526621

   ---

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: 386.38

Molecular Weight (Monoisotopic): 386.1390

AlogP: 2.70

#Rotatable Bonds: 6

Polar Surface Area: 104.90

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.37

CX LogD: 2.37

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: -0.48

References

1. Gong J, Gan J, Masson E, Syed S, Xia YQ, Williams D, Pursley J, Jemal M, Humphreys WG, Iyer RA..  (2012)  Metabolic chiral inversion of brivanib and its relevance to safety and pharmacology.,  40  (12): [PMID:22983304] [10.1124/dmd.112.047340]

2. Gong J, Gan J, Caceres-Cortes J, Christopher LJ, Arora V, Masson E, Williams D, Pursley J, Allentoff A, Lago M, Tran SB, Iyer RA..  (2011)  Metabolism and disposition of [14C]brivanib alaninate after oral administration to rats, monkeys, and humans.,  39  (5): [PMID:21289073] [10.1124/dmd.110.037341]

3. Gong J, Gan J, Iyer RA..  (2012)  Identification of the oxidative and conjugative enzymes involved in the biotransformation of brivanib.,  40  (1): [PMID:21989950] [10.1124/dmd.111.042457]

Source

Source(1):

• Scientific Literature