(2S)-2-(4-(1-(benzo[d]oxazol-2-yl)-5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-1-hydroxypentan-2-yl)benzamido)pentanedioic acid

ID: ALA272112

PubChem CID: 136152907

Max Phase: Preclinical

Molecular Formula: C28H30N6O8

Molecular Weight: 578.58

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: Nc1nc(N)c(CCCC(c2ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2)C(O)c2nc3ccccc3o2)c(=O)[nH]1

Standard InChI: InChI=1S/C28H30N6O8/c29-23-17(25(39)34-28(30)33-23)5-3-4-16(22(37)26-32-18-6-1-2-7-20(18)42-26)14-8-10-15(11-9-14)24(38)31-19(27(40)41)12-13-21(35)36/h1-2,6-11,16,19,22,37H,3-5,12-13H2,(H,31,38)(H,35,36)(H,40,41)(H5,29,30,33,34,39)/t16?,19-,22?/m0/s1

Standard InChI Key: AEBOOIADEBQAJC-UEUGHCDMSA-N

Molfile:

     RDKit          2D

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M  END

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

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

Calculated Properties

Molecular Weight: 578.58	Molecular Weight (Monoisotopic): 578.2125	AlogP: 1.96	#Rotatable Bonds: 13
Polar Surface Area: 247.75	Molecular Species: ACID	HBA: 10	HBD: 7
#RO5 Violations: 2	HBA (Lipinski): 14	HBD (Lipinski): 9	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.25	CX Basic pKa: ┄	CX LogP: 1.07	CX LogD: -5.59
Aromatic Rings: 4	Heavy Atoms: 42	QED Weighted: 0.12	Np Likeness Score: -0.12

References

1. Maryanoff BE, Costanzo MJ.. (2008) Inhibitors of proteases and amide hydrolases that employ an alpha-ketoheterocycle as a key enabling functionality., 16 (4): [PMID:18053726] [10.1016/j.bmc.2007.11.015]
2. Shih, C C, Habeck, L L LL, Mendelsohn, L G LG, Chen, V J VJ and Schultz, R M RM. 1998 Multiple folate enzyme inhibition: mechanism of a novel pyrrolopyrimidine-based antifolate LY231514 (MTA). [PMID:9762351]
3. Deng, Yijun and 6 more authors. 2008-08-28 Synthesis and discovery of high affinity folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity. [PMID:18680275]
4. Deng, Yijun Y and 7 more authors. 2009-05-14 Synthesis and biological activity of a novel series of 6-substituted thieno[2,3-d]pyrimidine antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors over the reduced folate carrier and proton-coupled folate transporter for cellular entry. [PMID:19371039]
5. Wang, Lei and 10 more authors. 2010-02-11 Synthesis and antitumor activity of a novel series of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitors of purine biosynthesis with selectivity for high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier for cellular entry. [PMID:20085328]
6. Wang, Lei and 6 more authors. 2012-02-23 Synthesis and biological activity of 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl regioisomers as inhibitors of de novo purine biosynthesis with selectivity for cellular uptake by high affinity folate receptors and the proton-coupled folate transporter over the reduced folate carrier. [PMID:22243528]
7. Wang, Yiqiang and 7 more authors. 2013-11-14 Tumor-targeting with novel non-benzoyl 6-substituted straight chain pyrrolo[2,3-d]pyrimidine antifolates via cellular uptake by folate receptor α and inhibition of de novo purine nucleotide biosynthesis. [PMID:24111942]
8. Golani, Lalit K and 9 more authors. 2014-10-09 Structure-activity profiles of novel 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolates with modified amino acids for cellular uptake by folate receptors α and β and the proton-coupled folate transporter. [PMID:25234128]
9. Wang, Yiqiang and 7 more authors. 2015-02-12 Novel 5-substituted pyrrolo[2,3-d]pyrimidines as dual inhibitors of glycinamide ribonucleotide formyltransferase and 5-aminoimidazole-4-carboxamide ribonucleotide formyltransferase and as potential antitumor agents. [PMID:25602637]
10. Wang, Lei and 16 more authors. 2015-09-10 6-Substituted Pyrrolo[2,3-d]pyrimidine Thienoyl Regioisomers as Targeted Antifolates for Folate Receptor α and the Proton-Coupled Folate Transporter in Human Tumors. [PMID:26317331]
11. Golani, Lalit K and 19 more authors. 2016-09-08 Tumor Targeting with Novel 6-Substituted Pyrrolo [2,3-d] Pyrimidine Antifolates with Heteroatom Bridge Substitutions via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis. [PMID:27458733]
12. Ravindra, Manasa and 11 more authors. 2018-03-08 Tumor Targeting with Novel Pyridyl 6-Substituted Pyrrolo[2,3- d]Pyrimidine Antifolates via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of De Novo Purine Nucleotide Biosynthesis. [PMID:29425443]
13. Ravindra, Manasa and 11 more authors. 2018-05-10 Fluorine-Substituted Pyrrolo[2,3- d]Pyrimidine Analogues with Tumor Targeting via Cellular Uptake by Folate Receptor α and the Proton-Coupled Folate Transporter and Inhibition of de Novo Purine Nucleotide Biosynthesis. [PMID:29701475]

(2S)-2-(4-(1-(benzo[d]oxazol-2-yl)-5-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-1-hydroxypentan-2-yl)benzamido)pentanedioic acid

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source