Nalpha-(4-amino-4-deoxypteroyl)-Ndelta-hemiphthaloyl-L-ornithine

ID: ALA4217422

PubChem CID: 145974729

Max Phase: Preclinical

Molecular Formula: C28H29N9O6

Molecular Weight: 587.60

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)N[C@@H](CCCNC(=O)c2ccccc2C(=O)O)C(=O)O)cc1

Standard InChI: InChI=1S/C28H29N9O6/c1-37(14-16-13-32-23-21(33-16)22(29)35-28(30)36-23)17-10-8-15(9-11-17)24(38)34-20(27(42)43)7-4-12-31-25(39)18-5-2-3-6-19(18)26(40)41/h2-3,5-6,8-11,13,20H,4,7,12,14H2,1H3,(H,31,39)(H,34,38)(H,40,41)(H,42,43)(H4,29,30,32,35,36)/t20-/m0/s1

Standard InChI Key: RUDKDTHAKYAYDC-FQEVSTJZSA-N

Molfile:

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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: 587.60	Molecular Weight (Monoisotopic): 587.2241	AlogP: 1.31	#Rotatable Bonds: 12
Polar Surface Area: 239.64	Molecular Species: ACID	HBA: 11	HBD: 6
#RO5 Violations: 3	HBA (Lipinski): 15	HBD (Lipinski): 8	#RO5 Violations (Lipinski): 3
CX Acidic pKa: 3.11	CX Basic pKa: 2.75	CX LogP: 0.86	CX LogD: -5.57
Aromatic Rings: 4	Heavy Atoms: 43	QED Weighted: 0.13	Np Likeness Score: -0.69

References

1. Ravindra M, Wallace-Povirk A, Karim MA, Wilson MR, O'Connor C, White K, Kushner J, Polin L, George C, Hou Z, Matherly LH, Gangjee A.. (2018) 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., 61 (5): [PMID:29425443] [10.1021/acs.jmedchem.7b01708]
2. Qiu, Andong A and 9 more authors. 2006-12-01 Identification of an intestinal folate transporter and the molecular basis for hereditary folate malabsorption. [PMID:17129779]
3. 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]
4. Wang, Lei and 13 more authors. 2011-10-27 Synthesis, biological, and antitumor activity of a highly potent 6-substituted pyrrolo[2,3-d]pyrimidine thienoyl antifolate inhibitor with proton-coupled folate transporter and folate receptor selectivity over the reduced folate carrier that inhibits β-glycinamide ribonucleotide formyltransferase. [PMID:21879757]
5. 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]
6. 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]
7. 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]
8. 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]
9. 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]
10. 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]
11. 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]

Nalpha-(4-amino-4-deoxypteroyl)-Ndelta-hemiphthaloyl-L-ornithine

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source