(S)-2-(4-{[N-methyl-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-6-yl)methylamino]-sulfonyl}phenylcarbonyl)aminopentanedioic acid

ID: ALA4548681

Chembl Id: CHEMBL4548681

PubChem CID: 137150145

Max Phase: Preclinical

Molecular Formula: C20H22N6O8S

Molecular Weight: 506.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN(Cc1cc2c(=O)[nH]c(N)nc2[nH]1)S(=O)(=O)c1ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc1

Standard InChI:  InChI=1S/C20H22N6O8S/c1-26(9-11-8-13-16(22-11)24-20(21)25-18(13)30)35(33,34)12-4-2-10(3-5-12)17(29)23-14(19(31)32)6-7-15(27)28/h2-5,8,14H,6-7,9H2,1H3,(H,23,29)(H,27,28)(H,31,32)(H4,21,22,24,25,30)/t14-/m0/s1

Standard InChI Key:  DCQIHMIPKMTNTF-AWEZNQCLSA-N

Alternative Forms

1. Parent:

   

   ALA4548681

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Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 506.50

Molecular Weight (Monoisotopic): 506.1220

AlogP: -0.30

#Rotatable Bonds: 10

Polar Surface Area: 228.64

Molecular Species: ACID

HBA: 8

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.64

CX Basic pKa: 4.50

CX LogP: -1.91

CX LogD: -7.54

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.21

Np Likeness Score: -0.67

References

1. Xiang W, Dekhne A, Doshi A, O'Connor C, Hou Z, Matherly LH, Gangjee A..  (2019)  Discovery of amide-bridged pyrrolo[2,3-d]pyrimidines as tumor targeted classical antifolates with selective uptake by folate receptor α and inhibition of de novo purine nucleotide biosynthesis.,  27  (23): [PMID:31679978] [10.1016/j.bmc.2019.115125]

Source

Source(1):

• Scientific Literature