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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:
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:
RDKit 2D
34 36 0 0 0 0 0 0 0 0999 V2000
11.7167 -16.2583 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
11.7167 -17.0833 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.4287 -17.4917 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
12.4287 -15.8417 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
12.4287 -15.0167 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
13.1407 -16.2583 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.1391 -17.0815 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.8500 -17.4927 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.5631 -17.0818 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
14.5607 -16.2555 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
13.8492 -15.8481 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.2739 -15.8407 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
15.9896 -16.2509 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
16.7028 -15.8362 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.4200 -16.2488 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.1326 -15.8347 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.1304 -15.0088 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.4096 -14.5988 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.6999 -15.0152 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.8430 -14.5931 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
18.8393 -13.7681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
19.5558 -14.9998 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
20.2682 -14.5837 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.9847 -14.9926 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.2640 -13.7587 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
20.9761 -13.3421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
19.5472 -13.3493 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
21.6971 -14.5765 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
22.4136 -14.9854 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
22.4187 -15.8116 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
23.1270 -14.5705 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
15.9923 -17.0759 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
16.7081 -17.4862 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
17.4167 -17.8958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
7 8 1 0
16 17 2 0
3 7 1 0
17 18 1 0
8 9 2 0
18 19 2 0
19 14 1 0
6 4 1 0
17 20 1 0
9 10 1 0
20 21 2 0
20 22 1 0
10 11 2 0
22 23 1 0
11 6 1 0
23 24 1 6
4 5 2 0
23 25 1 0
10 12 1 0
1 2 1 0
25 26 1 0
25 27 2 0
12 13 1 0
24 28 1 0
1 4 1 0
28 29 1 0
13 14 1 0
6 7 2 0
29 30 1 0
29 31 2 0
14 15 2 0
13 32 1 0
2 3 2 0
32 33 1 0
15 16 1 0
33 34 3 0
M END Associated Targets(Human) Associated Targets(non-human) Molecule Features Natural Product: NoOral: NoChemical Probe: NoParenteral: NoMolecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: NoChirality: NoAvailability: NoProdrug: No
Drug Indications MESH ID MESH Heading EFO IDs EFO Terms Max Phase for Indication References
Mechanisms of Action Mechanism of Action Action Type target ID Target Name Target Type Target Organism Binding Site Name References
Calculated Properties Molecular Weight: 462.46Molecular Weight (Monoisotopic): 462.1539AlogP: 1.61#Rotatable Bonds: 10Polar 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: -4.58Aromatic 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 ]