2-{4-Carboxy-4-[4-carboxy-4-(4-carboxy-4-{4-[(4-oxo-3,4-dihydro-quinazolin-6-ylmethyl)-prop-2-ynyl-amino]-benzoylamino}-butyrylamino)-butyrylamino]-butyrylamino}-pentanedioic acid;0.5trifluoroacetic acid

ID: ALA1202138

PubChem CID: 135998838

Max Phase: Preclinical

Molecular Formula: C41H44F3N7O17

Molecular Weight: 849.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CCN(Cc1ccc2ncnc(O)c2c1)c1ccc(C(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O)C(=O)O)C(=O)O)cc1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C39H43N7O15.C2HF3O2/c1-2-17-46(19-21-3-8-25-24(18-21)35(53)41-20-40-25)23-6-4-22(5-7-23)34(52)45-29(39(60)61)11-15-32(49)43-27(37(56)57)9-13-30(47)42-26(36(54)55)10-14-31(48)44-28(38(58)59)12-16-33(50)51;3-2(4,5)1(6)7/h1,3-8,18,20,26-29H,9-17,19H2,(H,42,47)(H,43,49)(H,44,48)(H,45,52)(H,50,51)(H,54,55)(H,56,57)(H,58,59)(H,60,61)(H,40,41,53);(H,6,7)/t26-,27-,28-,29-;/m0./s1

Standard InChI Key:  SCSZGDUATFUSPZ-MROKUPSKSA-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: 849.81

Molecular Weight (Monoisotopic): 849.2817

AlogP: 0.07

#Rotatable Bonds: 25

Polar Surface Area: 352.15

Molecular Species: ACID

HBA: 13

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 22

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.80

CX Basic pKa: 0.84

CX LogP: -0.12

CX LogD: -16.68

Aromatic Rings: 3

Heavy Atoms: 61

QED Weighted: 0.05

Np Likeness Score: -0.48

References

1. Bisset GM, Pawelczak K, Jackman AL, Calvert AH, Hughes LR..  (1992)  Syntheses and thymidylate synthase inhibitory activity of the poly-gamma-glutamyl conjugates of N-[5-[N-(3,4-dihydro-2-methyl-4-oxoquinazolin-6-ylmethyl)-N-methylamino ]-2-thenoyl]-L-glutamic acid (ICI D1694) and other quinazoline antifolates.,  35  (5): [PMID:1372358] [10.1021/jm00083a008]

Source

Source(1):

• Scientific Literature