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

ID: ALA172658

PubChem CID: 44384841

Max Phase: Preclinical

Molecular Formula: C23H28IN9O4

Molecular Weight: 621.44

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H28IN9O4/c1-33(12-14-11-28-20-18(29-14)19(25)31-23(26)32-20)15-7-5-13(6-8-15)21(35)30-16(22(36)37)4-2-3-9-27-17(34)10-24/h5-8,11,16H,2-4,9-10,12H2,1H3,(H,27,34)(H,30,35)(H,36,37)(H4,25,26,28,31,32)

Standard InChI Key:  NDRPUTRIAJPVPS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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  2  6  2  0
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 27 17  1  0
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 29 35  1  0
 30 12  1  0
 31 32  1  0
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 35 37  1  0
 36 34  1  0
 37 36  1  0
  3  4  1  0
 11 21  2  0
 24 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA172658

   2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-6-[(2-iodoacetyl)amino]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: 621.44

Molecular Weight (Monoisotopic): 621.1309

AlogP: 1.13

#Rotatable Bonds: 12

Polar Surface Area: 202.34

Molecular Species: ACID

HBA: 10

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.21

CX Basic pKa: 2.79

CX LogP: 0.75

CX LogD: -2.46

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.11

Np Likeness Score: -0.67

References

1. 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