Methotrexate alpha-monobutyl ester

ID: ALA3245814

Chembl Id: CHEMBL3245814

Cas Number: 66147-30-6

PubChem CID: 90672327

Max Phase: Preclinical

Molecular Formula: C24H30N8O5

Molecular Weight: 510.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H30N8O5/c1-3-4-11-37-23(36)17(9-10-18(33)34)29-22(35)14-5-7-16(8-6-14)32(2)13-15-12-27-21-19(28-15)20(25)30-24(26)31-21/h5-8,12,17H,3-4,9-11,13H2,1-2H3,(H,29,35)(H,33,34)(H4,25,26,27,30,31)/t17-/m0/s1

Standard InChI Key:  ACDMHLAVMTZWNJ-KRWDZBQOSA-N

Alternative Forms

1. Parent:

   

   ALA3245814

   1-Butyl hydrogen 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: 1.53

#Rotatable Bonds: 12

Polar Surface Area: 199.54

Molecular Species: ACID

HBA: 11

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 4.05

CX Basic pKa: 2.96

CX LogP: 1.47

CX LogD: -1.66

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.20

Np Likeness Score: -0.56

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]

Source

Source(1):

• Scientific Literature