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

ID: ALA142626

Cas Number: 51865-82-8

PubChem CID: 289162

Max Phase: Preclinical

Molecular Formula: C29H33N9O5

Molecular Weight: 587.64

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C29H33N9O5/c1-38(16-20-15-33-25-23(34-20)24(30)36-28(31)37-25)21-12-10-19(11-13-21)26(39)35-22(27(40)41)9-5-6-14-32-29(42)43-17-18-7-3-2-4-8-18/h2-4,7-8,10-13,15,22H,5-6,9,14,16-17H2,1H3,(H,32,42)(H,35,39)(H,40,41)(H4,30,31,33,36,37)

Standard InChI Key:  KWISOMZJDLWXAZ-UHFFFAOYSA-N

Molfile:  

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  4  3  2  0
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M  END

Alternative Forms

1. Parent:

   

   ALA142626

   2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-6-(phenylmethoxycarbonylamino)hexanoic acid

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: 587.64

Molecular Weight (Monoisotopic): 587.2605

AlogP: 2.50

#Rotatable Bonds: 13

Polar Surface Area: 211.57

Molecular Species: ACID

HBA: 11

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.46

CX Basic pKa: 2.87

CX LogP: 2.22

CX LogD: -1.01

Aromatic Rings: 4

Heavy Atoms: 43

QED Weighted: 0.14

Np Likeness Score: -0.65

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]

2. Rosowsky A, Wright JE, Ginty C, Uren J..  (1982)  Methotrexate analogues. 15. A methotrexate analogue designed for active-site-directed irreversible inactivation of dihydrofolate reductase.,  25  (8): [PMID:6811744] [10.1021/jm00350a015]

Source

Source(1):

• Scientific Literature