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

ID: ALA48645

PubChem CID: 10479741

Max Phase: Preclinical

Molecular Formula: C21H24N8O5

Molecular Weight: 468.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H24N8O5/c1-29(10-12-9-24-18-16(25-12)17(22)27-21(23)28-18)13-7-5-11(6-8-13)19(32)26-14(20(33)34)3-2-4-15(30)31/h5-9,14H,2-4,10H2,1H3,(H,26,32)(H,30,31)(H,33,34)(H4,22,23,24,27,28)

Standard InChI Key:  UGECVWNCMVBWTJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    2.9917   -1.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5292    0.2333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  2  6  2  0
  3  5  1  0
  4  2  1  0
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  7  3  1  0
  8 15  1  0
  9  4  1  0
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 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 32  1  0
 32 34  1  0
 33 13  1  0
 34 14  1  0
  4  3  2  0
 21 11  1  0
 24 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA48645

   2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]hexanedioic 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: 468.47

Molecular Weight (Monoisotopic): 468.1870

AlogP: 0.66

#Rotatable Bonds: 10

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: 3.31

CX Basic pKa: 2.83

CX LogP: 0.23

CX LogD: -6.09

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.28

Np Likeness Score: -0.48

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