(S)-dibutyl 2-(4-(((2,4-diaminopteridin-6-yl)methyl)(methyl)amino)benzamido)pentanedioate

ID: ALA3244639

Chembl Id: CHEMBL3244639

PubChem CID: 10370711

Max Phase: Preclinical

Molecular Formula: C28H38N8O5

Molecular Weight: 566.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCOC(=O)CC[C@H](NC(=O)c1ccc(N(C)Cc2cnc3nc(N)nc(N)c3n2)cc1)C(=O)OCCCC

Standard InChI:  InChI=1S/C28H38N8O5/c1-4-6-14-40-22(37)13-12-21(27(39)41-15-7-5-2)33-26(38)18-8-10-20(11-9-18)36(3)17-19-16-31-25-23(32-19)24(29)34-28(30)35-25/h8-11,16,21H,4-7,12-15,17H2,1-3H3,(H,33,38)(H4,29,30,31,34,35)/t21-/m0/s1

Standard InChI Key:  SPTBIJLJJBZGDY-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA3244639

   Methotrexate di-n-butyl ester

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: 566.66

Molecular Weight (Monoisotopic): 566.2965

AlogP: 2.79

#Rotatable Bonds: 15

Polar Surface Area: 188.54

Molecular Species: NEUTRAL

HBA: 12

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 3.00

CX LogP: 2.94

CX LogD: 2.94

Aromatic Rings: 3

Heavy Atoms: 41

QED Weighted: 0.18

Np Likeness Score: -0.58

References

1. Rosowsky A, Ensminger WD, Lazarus H, Yu CS..  (1977)  Methotrexate analogues. 8. Synthesis and biological evaluation of bisamide derivatives as potential prodrugs.,  20  (7): [PMID:406398] [10.1021/jm00217a012]

2. Rosowsky A, Beardsley GP, Ensminger WD, Lazarus H, Yu CS..  (1978)  Methotrexate analogues. 11. Unambiguous chemical synthesis and in vitro biological evaluation of alpha- and gamma-monoesters as potential prodrugs.,  21  (4): [PMID:565818] [10.1021/jm00202a013]

3. Rosowsky A, Beardsley GP, Ensminger WD, Lazarus H, Yu CS..  (1978)  Methotrexate analogues. 11. Unambiguous chemical synthesis and in vitro biological evaluation of alpha- and gamma-monoesters as potential prodrugs.,  21  (4): [PMID:565818] [10.1021/jm00202a013]

Source

Source(1):

• Scientific Literature