2-({4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-naphthalene-1-carbonyl}-amino)-pentanedioic acid

ID: ALA132431

PubChem CID: 425430

Max Phase: Preclinical

Molecular Formula: C24H24N8O5

Molecular Weight: 504.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(Cc1cnc2nc(N)nc(N)c2n1)c1ccc(C(=O)NC(CCC(=O)O)C(=O)O)c2ccccc12

Standard InChI:  InChI=1S/C24H24N8O5/c1-32(11-12-10-27-21-19(28-12)20(25)30-24(26)31-21)17-8-6-15(13-4-2-3-5-14(13)17)22(35)29-16(23(36)37)7-9-18(33)34/h2-6,8,10,16H,7,9,11H2,1H3,(H,29,35)(H,33,34)(H,36,37)(H4,25,26,27,30,31)

Standard InChI Key:  XNZUKUJONMYGIN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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 16  8  2  0
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 26 22  2  0
 27  5  1  0
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 30 29  1  0
 31 17  1  0
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 33 11  2  0
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 37 34  1  0
  3  4  1  0
 25 16  1  0
 11  9  1  0
 36 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA132431

   2-({4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-naphthalene-1-carbonyl}-amino)-pentanedioic 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: 504.51

Molecular Weight (Monoisotopic): 504.1870

AlogP: 1.42

#Rotatable Bonds: 9

Polar Surface Area: 210.54

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.47

CX Basic pKa: 2.87

CX LogP: 0.83

CX LogD: -5.43

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.22

Np Likeness Score: -0.52

References

1. Piper JR, Johnson CA, Maddry JA, Malik ND, McGuire JJ, Otter GM, Sirotnak FM..  (1993)  Studies on analogues of classical antifolates bearing the naphthoyl group in place of benzoyl in the side chain.,  36  (26): [PMID:8277497] [10.1021/jm00078a004]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays