2-[[(5aR)-2-(2-aminopyrimidin-5-yl)-5a,6,8,9-tetrahydro-5H-pyrimido[1,2]pyrrolo[4,5-a][1,4]oxazin-4-yl]-(2-hydroxyethyl)amino]propanal

ID: ALA4521919

PubChem CID: 155542784

Max Phase: Preclinical

Molecular Formula: C18H23N7O3

Molecular Weight: 385.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C=O)N(CCO)c1nc(-c2cnc(N)nc2)nc2c1C[C@@H]1COCCN21

Standard InChI:  InChI=1S/C18H23N7O3/c1-11(9-27)24(2-4-26)16-14-6-13-10-28-5-3-25(13)17(14)23-15(22-16)12-7-20-18(19)21-8-12/h7-9,11,13,26H,2-6,10H2,1H3,(H2,19,20,21)/t11?,13-/m1/s1

Standard InChI Key:  RFCQCOSQCVGWHQ-GLGOKHISSA-N

Molfile:  

 
     RDKit          2D

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    4.9804  -15.3366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845  -15.7433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6845  -16.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9829  -16.9652    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2765  -16.5639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4975  -16.8155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0133  -16.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4976  -15.4922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1997  -16.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8662  -16.9866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3462  -17.6483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1640  -17.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8042  -15.3617    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3964  -16.9685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1043  -16.5589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8126  -16.9679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8126  -17.7879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1069  -18.1968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3964  -17.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5203  -18.1978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9804  -14.5169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2726  -14.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2726  -13.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5649  -12.8776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6922  -14.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6922  -13.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3999  -12.8776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3999  -14.5169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  7 13  1  0
  8 14  1  6
 15  4  1  0
 16 15  2  0
 17 16  1  0
 18 17  2  0
 19 18  1  0
 20 19  2  0
 15 20  1  0
 18 21  1  0
  2 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 22 26  1  0
 26 27  1  0
 27 28  2  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4521919

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 385.43

Molecular Weight (Monoisotopic): 385.1862

AlogP: -0.34

#Rotatable Bonds: 6

Polar Surface Area: 130.59

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.61

CX LogP: 0.82

CX LogD: 0.82

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.64

Np Likeness Score: -0.58

References

1. Borsari C, Rageot D, Dall'Asen A, Bohnacker T, Melone A, Sele AM, Jackson E, Langlois JB, Beaufils F, Hebeisen P, Fabbro D, Hillmann P, Wymann MP..  (2019)  A Conformational Restriction Strategy for the Identification of a Highly Selective Pyrimido-pyrrolo-oxazine mTOR Inhibitor.,  62  (18): [PMID:31465220] [10.1021/acs.jmedchem.9b00972]

Source

Source(1):

• Scientific Literature