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5-methyl-6-(naphthalen-2-ylthio)-7H-pyrrolo[2,3-d]pyrimidine-2,4-diamine ID: ALA227065
PubChem CID: 23647976
Max Phase: Preclinical
Molecular Formula: C17H15N5S
Molecular Weight: 321.41
Molecule Type: Small molecule
Associated Items:
Names and Identifiers Canonical SMILES: Cc1c(Sc2ccc3ccccc3c2)[nH]c2nc(N)nc(N)c12
Standard InChI: InChI=1S/C17H15N5S/c1-9-13-14(18)20-17(19)22-15(13)21-16(9)23-12-7-6-10-4-2-3-5-11(10)8-12/h2-8H,1H3,(H5,18,19,20,21,22)
Standard InChI Key: HYATWDPIRHVVDH-UHFFFAOYSA-N
Molfile:
RDKit 2D
23 26 0 0 0 0 0 0 0 0999 V2000
3.3520 -5.6238 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.5270 -5.6238 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1145 -4.9093 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.7645 -4.9093 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.1145 -6.3383 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
4.5895 -4.9093 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
3.3520 -4.1949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.5270 -4.1949 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.2720 -3.4103 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
2.9395 -2.9253 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6069 -3.4103 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.3915 -3.1553 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
2.9395 -2.1003 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0
3.6540 -1.6878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
3.6540 -0.8628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.3684 -0.4503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4.3684 -2.1003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0829 -1.6878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.0829 -0.8628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7974 -0.4503 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.5118 -0.8628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
6.5118 -1.6878 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
5.7974 -2.1003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
11 7 1 0
2 5 1 0
11 12 1 0
2 3 1 0
10 13 1 0
4 6 1 0
13 14 1 0
7 8 1 0
14 15 2 0
3 8 2 0
15 16 1 0
16 19 2 0
17 14 1 0
17 18 2 0
1 2 2 0
7 4 2 0
4 1 1 0
18 19 1 0
19 20 1 0
8 9 1 0
20 21 2 0
9 10 1 0
21 22 1 0
10 11 2 0
22 23 2 0
23 18 1 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: 321.41Molecular Weight (Monoisotopic): 321.1048AlogP: 3.74#Rotatable Bonds: 2Polar Surface Area: 93.61Molecular Species: NEUTRALHBA: 5HBD: 3#RO5 Violations: ┄HBA (Lipinski): 5HBD (Lipinski): 5#RO5 Violations (Lipinski): ┄CX Acidic pKa: 12.35CX Basic pKa: 8.36CX LogP: 3.91CX LogD: 2.93Aromatic Rings: 4Heavy Atoms: 23QED Weighted: 0.52Np Likeness Score: -0.70
References 1. Gangjee A, Zeng Y, Talreja T, McGuire JJ, Kisliuk RL, Queener SF.. (2007) Design and synthesis of classical and nonclassical 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines as antifolates., 50 (13): [PMID:17552508 ] [10.1021/jm070165j ] 2. Gangjee A, Lin X, Biondo LR, Queener SF.. (2010) CoMFA analysis of tgDHFR and rlDHFR based on antifolates with 6-5 fused ring system using the all-orientation search (AOS) routine and a modified cross-validated r(2)-guided region selection (q(2)-GRS) routine and its initial application., 18 (4): [PMID:20117005 ] [10.1016/j.bmc.2009.12.066 ] 3. Shah K, Lin X, Queener SF, Cody V, Pace J, Gangjee A.. (2018) Targeting species specific amino acid residues: Design, synthesis and biological evaluation of 6-substituted pyrrolo[2,3-d]pyrimidines as dihydrofolate reductase inhibitors and potential anti-opportunistic infection agents., 26 (9): [PMID:29691153 ] [10.1016/j.bmc.2018.04.032 ]