(S)-2-(5-(3-(2,4-diaminofuro[2,3-d]pyrimidin-5-yl)propyl)thiophene-3-carboxamido)pentanedioic acid

ID: ALA3628347

Chembl Id: CHEMBL3628347

PubChem CID: 67092918

Max Phase: Preclinical

Molecular Formula: C19H21N5O6S

Molecular Weight: 447.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2c(CCCc3cc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cs3)coc2n1

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

Standard InChI Key:  YSCGOYFEYRSGDL-LBPRGKRZSA-N

Alternative Forms

1. Parent:

   

   ALA3628347

   (S)-2-({5-[3-(2,4-Diamino-furo[2,3-d]pyrimidin-5-yl)-propyl]-thiophene-3-carbonyl}-amino)-pentanedioic acid

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: 1.67

#Rotatable Bonds: 10

Polar Surface Area: 194.66

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.67

CX Basic pKa: 5.35

CX LogP: 0.14

CX LogD: -4.34

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.30

Np Likeness Score: -0.33

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]

Source

Source(1):

• Scientific Literature