(S)-2-({4-[3-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]-pyrimidin-6-yl)-propyl]-thiophene-2-carbonyl}-amino)-pentanedioic Acid

ID: ALA3628344

Chembl Id: CHEMBL3628344

PubChem CID: 135567034

Max Phase: Preclinical

Molecular Formula: C19H21N5O6S

Molecular Weight: 447.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc2[nH]c(CCCc3csc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)c3)cc2c(=O)[nH]1

Standard InChI:  InChI=1S/C19H21N5O6S/c20-19-23-15-11(16(27)24-19)7-10(21-15)3-1-2-9-6-13(31-8-9)17(28)22-12(18(29)30)4-5-14(25)26/h6-8,12H,1-5H2,(H,22,28)(H,25,26)(H,29,30)(H4,20,21,23,24,27)/t12-/m0/s1

Standard InChI Key:  UNSSSMUKJOLMJV-LBPRGKRZSA-N

Alternative Forms

1. Parent:

   

   ALA3628344

   ---

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

Calculated Properties

Molecular Weight: 447.47

Molecular Weight (Monoisotopic): 447.1213

AlogP: 1.12

#Rotatable Bonds: 10

Polar Surface Area: 191.26

Molecular Species: ACID

HBA: 7

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.63

CX Basic pKa: 4.82

CX LogP: 0.13

CX LogD: -4.97

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.27

Np Likeness Score: -0.15

References

1. Wang L, Wallace A, Raghavan S, Deis SM, Wilson MR, Yang S, Polin L, White K, Kushner J, Orr S, George C, O'Connor C, Hou Z, Mitchell-Ryan S, Dann CE, Matherly LH, Gangjee A..  (2015)  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.,  58  (17): [PMID:26317331] [10.1021/acs.jmedchem.5b00801]

2. Ravindra M, Wilson MR, Tong N, O'Connor C, Karim M, Polin L, Wallace-Povirk A, White K, Kushner J, Hou Z, Matherly LH, Gangjee A..  (2018)  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.,  61  (9): [PMID:29701475] [10.1021/acs.jmedchem.8b00408]

Source

Source(1):

• Scientific Literature