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(2S)-2-(5-{[(2-Amino-4-oxo-3,4-dihydro[1]benzothieno-[2,3-d]pyrimidin-5-yl)methyl]amino}-1-oxo-1,3-dihydro-2H-isoindol-2-yl)pentanedioic acid

ID: ALA1738740

PubChem CID: 52914861

Max Phase: Preclinical

Molecular Formula: C24H21N5O6S

Molecular Weight: 507.53

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  Nc1nc2sc3cccc(CNc4ccc5c(c4)CN([C@@H](CCC(=O)O)C(=O)O)C5=O)c3c2c(=O)[nH]1

Standard InChI:  InChI=1S/C24H21N5O6S/c25-24-27-20(32)19-18-11(2-1-3-16(18)36-21(19)28-24)9-26-13-4-5-14-12(8-13)10-29(22(14)33)15(23(34)35)6-7-17(30)31/h1-5,8,15,26H,6-7,9-10H2,(H,30,31)(H,34,35)(H3,25,27,28,32)/t15-/m0/s1

Standard InChI Key:  QPDXRVRRCIFNSL-HNNXBMFYSA-N

Molfile:  

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    0.0000   -1.3190    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Associated Targets(Human)

TYMS Tclin Thymidylate synthase (1651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DHFR Tclin Dihydrofolate reductase (3072 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

thyA Thymidylate synthase (EC 2.1.1.45) (TS) (TSase) (9 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dihydrofolate reductase (1637 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
folA Dihydrofolate reductase (1415 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

Calculated Properties

Molecular Weight: 507.53Molecular Weight (Monoisotopic): 507.1213AlogP: 2.61#Rotatable Bonds: 8
Polar Surface Area: 178.71Molecular Species: ACIDHBA: 8HBD: 5
#RO5 Violations: 1HBA (Lipinski): 11HBD (Lipinski): 6#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.28CX Basic pKa: 2.98CX LogP: 0.57CX LogD: -5.10
Aromatic Rings: 4Heavy Atoms: 36QED Weighted: 0.24Np Likeness Score: -0.64

References

1. Zhang X, Zhou X, Kisliuk RL, Piraino J, Cody V, Gangjee A..  (2011)  Design, synthesis, biological evaluation and X-ray crystal structure of novel classical 6,5,6-tricyclic benzo[4,5]thieno[2,3-d]pyrimidines as dual thymidylate synthase and dihydrofolate reductase inhibitors.,  19  (11): [PMID:21550809] [10.1016/j.bmc.2011.03.067]

Source