Methotrexate diethyl ester

ID: ALA3245817

Chembl Id: CHEMBL3245817

Cas Number: 43170-88-3

PubChem CID: 94528

Max Phase: Preclinical

Molecular Formula: C24H30N8O5

Molecular Weight: 510.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H30N8O5/c1-4-36-18(33)11-10-17(23(35)37-5-2)29-22(34)14-6-8-16(9-7-14)32(3)13-15-12-27-21-19(28-15)20(25)30-24(26)31-21/h6-9,12,17H,4-5,10-11,13H2,1-3H3,(H,29,34)(H4,25,26,27,30,31)/t17-/m0/s1

Standard InChI Key:  MZRRIAJJDAPQRO-KRWDZBQOSA-N

Alternative Forms

1. Parent:

   

   ALA3245817

   Diethyl N-(4-(((2,4-diamino-6-pteridinyl)methyl)methylamino)benzoyl)-L-glutamate

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: 510.56

Molecular Weight (Monoisotopic): 510.2339

AlogP: 1.23

#Rotatable Bonds: 11

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: 1.00

CX LogD: 1.00

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.31

Np Likeness Score: -0.71

References

1. 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]

2. Yang X, Wedajo W, Yamada Y, Dahlroth SL, Neo JJ, Dick T, Chui WK..  (2018)  1,3,5-triazaspiro[5.5]undeca-2,4-dienes as selective Mycobacterium tuberculosis dihydrofolate reductase inhibitors with potent whole cell activity.,  144  [PMID:29274493] [10.1016/j.ejmech.2017.12.017]

Source

Source(1):

• Scientific Literature