(3R,5S)-5-((4-(1-(thiophen-3-ylsulfonyl)-1H-indol-5-ylamino)thieno[3,2-d]pyrimidin-6-yl)ethynyl)pyrrolidin-3-yl morpholine-4-carboxylate

ID: ALA452768

PubChem CID: 44564704

Max Phase: Preclinical

Molecular Formula: C29H26N6O5S3

Molecular Weight: 634.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O[C@H]1CN[C@H](C#Cc2cc3ncnc(Nc4ccc5c(ccn5S(=O)(=O)c5ccsc5)c4)c3s2)C1)N1CCOCC1

Standard InChI:  InChI=1S/C29H26N6O5S3/c36-29(34-8-10-39-11-9-34)40-22-14-20(30-16-22)1-3-23-15-25-27(42-23)28(32-18-31-25)33-21-2-4-26-19(13-21)5-7-35(26)43(37,38)24-6-12-41-17-24/h2,4-7,12-13,15,17-18,20,22,30H,8-11,14,16H2,(H,31,32,33)/t20-,22-/m1/s1

Standard InChI Key:  HAYQBGMCBFKTMA-IFMALSPDSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA452768

   [(3R,5S)-5-[2-[4-[(1-thiophen-3-ylsulfonylindol-5-yl)amino]thieno[3,2-d]pyrimidin-6-yl]ethynyl]pyrrolidin-3-yl] morpholine-4-carboxylate

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: 634.77

Molecular Weight (Monoisotopic): 634.1127

AlogP: 4.24

#Rotatable Bonds: 5

Polar Surface Area: 127.68

Molecular Species: NEUTRAL

HBA: 12

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.25

CX LogP: 3.97

CX LogD: 3.07

Aromatic Rings: 5

Heavy Atoms: 43

QED Weighted: 0.27

Np Likeness Score: -1.24

References

1. Waterson AG, Petrov KG, Hornberger KR, Hubbard RD, Sammond DM, Smith SC, Dickson HD, Caferro TR, Hinkle KW, Stevens KL, Dickerson SH, Rusnak DW, Spehar GM, Wood ER, Griffin RJ, Uehling DE..  (2009)  Synthesis and evaluation of aniline headgroups for alkynyl thienopyrimidine dual EGFR/ErbB-2 kinase inhibitors.,  19  (5): [PMID:19208477] [10.1016/j.bmcl.2009.01.080]

Source

Source(1):

• Scientific Literature