(2S)-2-(4-(6-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-1,1,1-trifluoro-2-oxohexan-3-yl)benzamido)pentanedioic acid

ID: ALA451818

PubChem CID: 135474781

Max Phase: Preclinical

Molecular Formula: C22H24F3N5O7

Molecular Weight: 527.46

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(C(=O)C(F)(F)F)c2ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc2)c(=O)[nH]1

Standard InChI: InChI=1S/C22H24F3N5O7/c23-22(24,25)16(33)12(2-1-3-13-17(26)29-21(27)30-19(13)35)10-4-6-11(7-5-10)18(34)28-14(20(36)37)8-9-15(31)32/h4-7,12,14H,1-3,8-9H2,(H,28,34)(H,31,32)(H,36,37)(H5,26,27,29,30,35)/t12?,14-/m0/s1

Standard InChI Key: GMLVQBYTPQKEQF-PYMCNQPYSA-N

Molfile:

     RDKit          2D

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    5.3667   -1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0787   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7907   -1.6958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7907   -0.8708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0787   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6510   -0.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6486    0.3646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3618    0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0775    0.3688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7908    0.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5045    0.3676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2156    0.7787    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2175    1.6041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5020    2.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7846    1.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2196   -1.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.9335   -2.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6486   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3625   -2.1135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6498   -0.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9323   -2.9364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6462   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6450   -4.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3589   -4.5885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9299   -4.5864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9377   -0.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2221   -0.4646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401   -1.7000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5042   -0.0500    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8105   -1.1797    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  2  0
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  4  5  1  0
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  5  6  2  0
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  1  7  1  0
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  1  2  2  0
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 11 16  2  0
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 13 14  1  0
  7 32  1  0
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 15 16  1  0
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  7  8  1  0
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  1  6  1  0
 33 37  1  0
M  END

Associated Targets(Human)

GART Tclin GAR transformylase (531 Activities)

Discover Target: GART

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ATIC Tchem AICAR transformylase (241 Activities)

Discover Target: ATIC

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CCRF-CEM (65223 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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: 527.46	Molecular Weight (Monoisotopic): 527.1628	AlogP: 1.22	#Rotatable Bonds: 12
Polar Surface Area: 218.56	Molecular Species: ACID	HBA: 8	HBD: 6
#RO5 Violations: 2	HBA (Lipinski): 12	HBD (Lipinski): 8	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.25	CX Basic pKa: ┄	CX LogP: 1.47	CX LogD: -5.18
Aromatic Rings: 2	Heavy Atoms: 37	QED Weighted: 0.23	Np Likeness Score: -0.09

References

1. DeMartino JK, Hwang I, Connelly S, Wilson IA, Boger DL.. (2008) Asymmetric synthesis of inhibitors of glycinamide ribonucleotide transformylase., 51 (17): [PMID:18686942] [10.1021/jm800555h]
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-(6-(2,4-diamino-6-oxo-1,6-dihydropyrimidin-5-yl)-1,1,1-trifluoro-2-oxohexan-3-yl)benzamido)pentanedioic acid

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source