N-[4-[(2-amino-6-mtehyl-3,4-dihydro-4-oxo-7H-pyrrolo[2,3-d]pyrimidin-5-yl)thio]-2'chlorobenzoyl]-L-glutamic acid

ID: ALA224868

Chembl Id: CHEMBL224868

PubChem CID: 135545856

Max Phase: Preclinical

Molecular Formula: C19H18ClN5O6S

Molecular Weight: 479.90

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  Cc1[nH]c2nc(N)[nH]c(=O)c2c1Sc1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c(Cl)c1

Standard InChI:  InChI=1S/C19H18ClN5O6S/c1-7-14(13-15(22-7)24-19(21)25-17(13)29)32-8-2-3-9(10(20)6-8)16(28)23-11(18(30)31)4-5-12(26)27/h2-3,6,11H,4-5H2,1H3,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t11-/m0/s1

Standard InChI Key:  DTVBRZFMWHDIOO-NSHDSACASA-N

Alternative Forms

  1. Parent:

    ALA224868

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Associated Targets(Human)

FPGS Tchem Folylpoly-gamma-glutamate synthetase (250 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
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
CCRF-CEM (65223 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
R2 (178 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
EKVX (44102 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HCC 2998 (41480 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SF-268 (49410 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NCI/ADR-RES (33767 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
BT-549 (31254 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

folA Dihydrofolate reductase (1415 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
thyA Thymidylate synthase (595 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
R1 (16 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

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 479.90Molecular Weight (Monoisotopic): 479.0666AlogP: 1.99#Rotatable Bonds: 8
Polar Surface Area: 191.26Molecular Species: ACIDHBA: 7HBD: 6
#RO5 Violations: 1HBA (Lipinski): 11HBD (Lipinski): 7#RO5 Violations (Lipinski): 2
CX Acidic pKa: 2.97CX Basic pKa: 2.34CX LogP: 0.98CX LogD: -5.34
Aromatic Rings: 3Heavy Atoms: 32QED Weighted: 0.28Np Likeness Score: -0.65

References

1. Gangjee A, Jain HD, McGuire JJ, Kisliuk RL..  (2004)  Benzoyl ring halogenated classical 2-amino-6-methyl-3,4-dihydro-4-oxo-5-substituted thiobenzoyl-7H-pyrrolo[2,3-d]pyrimidine antifolates as inhibitors of thymidylate synthase and as antitumor agents.,  47  (27): [PMID:15615522] [10.1021/jm040144e]
2. Kumar VP, Frey KM, Wang Y, Jain HK, Gangjee A, Anderson KS..  (2013)  Substituted pyrrolo[2,3-d]pyrimidines as Cryptosporidium hominis thymidylate synthase inhibitors.,  23  (19): [PMID:23927969] [10.1016/j.bmcl.2013.07.037]

Source