2-{4-[(4-Oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-pentanedioic acid

ID: ALA103059

PubChem CID: 136056561

Max Phase: Preclinical

Molecular Formula: C24H22N4O6

Molecular Weight: 462.46

Molecule Type: Small molecule

Associated Items:

This compound is not in our inventory system

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1ccc2nc[nH]c(=O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C24H22N4O6/c1-2-11-28(13-15-3-8-19-18(12-15)23(32)26-14-25-19)17-6-4-16(5-7-17)22(31)27-20(24(33)34)9-10-21(29)30/h1,3-8,12,14,20H,9-11,13H2,(H,27,31)(H,29,30)(H,33,34)(H,25,26,32)/t20-/m0/s1

Standard InChI Key:  AOGOUTMDEVCZHA-FQEVSTJZSA-N

Molfile:  

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M  END

Alternative Forms

  1. Parent:

    ALA103059

    ---

Associated Targets(Human)

TYMS Tclin Thymidylate synthase (1651 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Tyms Thymidylate synthase (842 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L1210 (27553 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
L1210 (R7A) (18 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Dhfr Dihydrofolate reductase (2343 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: 462.46Molecular Weight (Monoisotopic): 462.1539AlogP: 1.61#Rotatable Bonds: 10
Polar Surface Area: 152.69Molecular Species: ACIDHBA: 6HBD: 4
#RO5 Violations: HBA (Lipinski): 10HBD (Lipinski): 4#RO5 Violations (Lipinski):
CX Acidic pKa: 3.23CX Basic pKa: 5.05CX LogP: 0.40CX LogD: -4.58
Aromatic Rings: 3Heavy Atoms: 34QED Weighted: 0.33Np Likeness Score: -0.81

References

1. Hughes LR, Jackman AL, Oldfield J, Smith RC, Burrows KD, Marsham PR, Bishop JA, Jones TR, O'Connor BM, Calvert AH..  (1990)  Quinazoline antifolate thymidylate synthase inhibitors: alkyl, substituted alkyl, and aryl substituents in the C2 position.,  33  (11): [PMID:2231606] [10.1021/jm00173a024]
2. Jackman AL, Marsham PR, Thornton TJ, Bishop JA, O'Connor BM, Hughes LR, Calvert AH, Jones TR..  (1990)  Quinazoline antifolate thymidylate synthase inhibitors: 2'-fluoro-N10-propargyl-5,8-dideazafolic acid and derivatives with modifications in the C2 position.,  33  (11): [PMID:2231607] [10.1021/jm00173a025]
3. Bisset GM, Pawelczak K, Jackman AL, Calvert AH, Hughes LR..  (1992)  Syntheses and thymidylate synthase inhibitory activity of the poly-gamma-glutamyl conjugates of N-[5-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino ]-2-thenoyl]-L-glutamic acid (ICI D1694) and other quinazoline antifolates.,  35  (5): [PMID:1372358] [10.1021/jm00083a008]
4. Srivastava V, Gupta SP, Siddiqi MI, Mishra BN..  (2010)  3D-QSAR studies on quinazoline antifolate thymidylate synthase inhibitors by CoMFA and CoMSIA models.,  45  (4): [PMID:20153089] [10.1016/j.ejmech.2009.12.065]

Source