2-{4-[(2,4-Diamino-pteridin-6-ylmethyl)-methyl-amino]-benzoylamino}-heptanedioic acid

ID: ALA47278

PubChem CID: 44292865

Max Phase: Preclinical

Molecular Formula: C22H26N8O5

Molecular Weight: 482.50

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H26N8O5/c1-30(11-13-10-25-19-17(26-13)18(23)28-22(24)29-19)14-8-6-12(7-9-14)20(33)27-15(21(34)35)4-2-3-5-16(31)32/h6-10,15H,2-5,11H2,1H3,(H,27,33)(H,31,32)(H,34,35)(H4,23,24,25,28,29)

Standard InChI Key:  OOTDXCUPXQETAY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    5.8042   -8.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -7.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -8.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2542   -7.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3500   -6.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -7.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -5.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.4000   -3.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -7.0292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -5.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542   -7.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -6.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -8.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8625   -5.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3625   -3.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -6.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792   -3.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8417   -5.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3542   -4.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3542   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  2  0
  3  5  1  0
  4  2  1  0
  5  1  2  0
  6  1  1  0
  7  3  1  0
  8 15  1  0
  9  4  1  0
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 11  7  2  0
 12 14  1  0
 13 16  1  0
 14 10  1  0
 15 25  1  0
 16 11  1  0
 17 13  1  0
 18 32  1  0
 19  8  2  0
 20 12  2  0
 21  9  2  0
 22 18  2  0
 23  5  1  0
 24 26  1  0
 25 27  2  0
 26 17  2  0
 27 17  1  0
 28  6  1  0
 29 12  1  0
 30 18  1  0
 31 13  1  0
 32 34  1  0
 33 14  1  0
 34 35  1  0
 35 33  1  0
  4  3  2  0
 21 11  1  0
 24 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA47278

   2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]heptanedioic 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: 482.50

Molecular Weight (Monoisotopic): 482.2026

AlogP: 1.05

#Rotatable Bonds: 11

Polar Surface Area: 210.54

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.36

CX Basic pKa: 2.84

CX LogP: 0.69

CX LogD: -5.63

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.24

Np Likeness Score: -0.46

References

1. Rosowsky A, Forsch R, Uren J, Wick M, Kumar AA, Freisheim JH..  (1983)  Methotrexate analogues. 20. Replacement of glutamate by longer-chain amino diacids: effects on dihydrofolate reductase inhibition, cytotoxicity, and in vivo antitumor activity.,  26  (12): [PMID:6139480] [10.1021/jm00366a012]

Source

Source(1):

• Scientific Literature