6-Benzyloxycarbonylamino-2-{4-[(2,4-diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-hexanoic acid tert-butyl ester

ID: ALA342744

PubChem CID: 44362567

Max Phase: Preclinical

Molecular Formula: C33H41N9O5

Molecular Weight: 643.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)NC(CCCCNC(=O)OCc2ccccc2)C(=O)OC(C)(C)C)cc1

Standard InChI:  InChI=1S/C33H41N9O5/c1-33(2,3)47-30(44)25(12-8-9-17-36-32(45)46-20-21-10-6-5-7-11-21)39-29(43)22-13-15-24(16-14-22)42(4)19-23-18-37-28-26(38-23)27(34)40-31(35)41-28/h5-7,10-11,13-16,18,25H,8-9,12,17,19-20H2,1-4H3,(H,36,45)(H,39,43)(H4,34,35,37,40,41)

Standard InChI Key:  FFFZUWQOMXIVFB-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA342744

   Tert-butyl 2-[[4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-6-(phenylmethoxycarbonylamino)hexanoate

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: 643.75

Molecular Weight (Monoisotopic): 643.3231

AlogP: 3.76

#Rotatable Bonds: 13

Polar Surface Area: 200.57

Molecular Species: NEUTRAL

HBA: 12

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 3.00

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 4

Heavy Atoms: 47

QED Weighted: 0.12

Np Likeness Score: -0.71

References

1. Kempton RJ, Black AM, Anstead GM, Kumar AA, Blankenship DT, Freisheim JH..  (1982)  Lysine and ornithine analogues of methotrexate as inhibitors of dihydrofolate reductase.,  25  (4): [PMID:7069726] [10.1021/jm00346a026]

Source

Source(1):

• Scientific Literature