(R)-2-((S)-4-Carboxy-4-{4-[(2-methyl-4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-pentanedioic acid TFA

ID: ALA170789

PubChem CID: 136078510

Max Phase: Preclinical

Molecular Formula: C32H32F3N5O11

Molecular Weight: 605.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1ccc2nc(C)nc(O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)N[C@H](CCC(=O)O)C(=O)O)C(=O)O)cc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C30H31N5O9.C2HF3O2/c1-3-14-35(16-18-4-9-22-21(15-18)28(40)32-17(2)31-22)20-7-5-19(6-8-20)27(39)34-24(30(43)44)10-12-25(36)33-23(29(41)42)11-13-26(37)38;3-2(4,5)1(6)7/h1,4-9,15,23-24H,10-14,16H2,2H3,(H,33,36)(H,34,39)(H,37,38)(H,41,42)(H,43,44)(H,31,32,40);(H,6,7)/t23-,24+;/m1./s1

Standard InChI Key:  WNDVTFYGTFPZBO-ITNPDYSASA-N

Molfile:  

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M  END

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: 605.60

Molecular Weight (Monoisotopic): 605.2122

AlogP: 1.68

#Rotatable Bonds: 15

Polar Surface Area: 219.35

Molecular Species: ACID

HBA: 9

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.06

CX Basic pKa: 1.74

CX LogP: 2.04

CX LogD: -7.64

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.14

Np Likeness Score: -0.78

References

1. Bavetsias V, Jackman AL, Kimbell R, Gibson W, Boyle FT, Bisset GM..  (1996)  Quinazoline antifolate thymidylate synthase inhibitors: gamma-linked L-D, D-D, and D-L dipeptide analogues of 2-desamino-2-methyl-N10-propargyl-5,8-dideazafolic acid (ICI 198583).,  39  (1): [PMID:8568829] [10.1021/jm950471+]

Source

Source(1):

• Scientific Literature