Standard InChI: InChI=1S/C22H23N5O6/c1-11-14(6-7-15-18(11)20(31)27-22(23)26-15)24-10-12-2-4-13(5-3-12)19(30)25-16(21(32)33)8-9-17(28)29/h2-7,16,24H,8-10H2,1H3,(H,25,30)(H,28,29)(H,32,33)(H3,23,26,27,31)
Standard InChI Key: PWDUHBWWDCSSPY-UHFFFAOYSA-N
Associated Targets(Human)
HT-29 80576 Activities
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SW480 6023 Activities
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WiDr 1835 Activities
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Dihydrofolate reductase 3072 Activities
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HuTu80 255 Activities
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Associated Targets(non-human)
Thymidylate synthase 842 Activities
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Thymidylate synthase 501 Activities
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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
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Properties
Molecular Weight: 453.46
Molecular Weight (Monoisotopic): 453.1648
AlogP: 1.89
#Rotatable Bonds: 9
Polar Surface Area: 187.76
Molecular Species: ACID
HBA: 8
HBD: 6
#RO5 Violations: 1
HBA (Lipinski): 11
HBD (Lipinski): 7
#RO5 Violations (Lipinski): 2
CX Acidic pKa: 3.29
CX Basic pKa: 2.67
CX LogP: 1.54
CX LogD: -4.53
Aromatic Rings: 3
Heavy Atoms: 33
QED Weighted: 0.28
Np Likeness Score: -0.55
References
1.Hynes JB, Kumar A, Tomazic A, Washtien WL.. (1987) Synthesis of 5-chloro-5,8-dideaza analogues of folic acid and aminopterin targeted for colon adenocarcinoma., 30 (8):[PMID:3612694][10.1021/jm00391a042]
2.Hynes JB, Yang YC, McGill JE, Harmon SJ, Washtien WL.. (1984) Improved synthesis and antitumor evaluation of 5,8-dideazaisofolic acid and closely related analogues., 27 (2):[PMID:6694171][10.1021/jm00368a023]
3.Hynes JB, Patil SA, Tomazic A, Kumar A, Pathak A, Tan XH, Li XQ, Ratnam M, Delcamp TJ, Freisheim JH.. (1988) Inhibition of murine thymidylate synthase and human dihydrofolate reductase by 5,8-dideaza analogues of folic acid and aminopterin., 31 (2):[PMID:3339615][10.1021/jm00397a031]
4.Chen BK, Horváth C, Bertino JR.. (1979) Multivariate analysis and quantitative structure-activity relationships. Inhibition of dihydrofolate reductase and thymidylate synthetase by quinazolines., 22 (5):[PMID:110930][10.1021/jm00191a005]
