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

ID: ALA356340

PubChem CID: 44362619

Max Phase: Preclinical

Molecular Formula: C28H31N9O5

Molecular Weight: 573.61

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H31N9O5/c1-37(15-19-14-32-24-22(33-19)23(29)35-27(30)36-24)20-11-9-18(10-12-20)25(38)34-21(26(39)40)8-5-13-31-28(41)42-16-17-6-3-2-4-7-17/h2-4,6-7,9-12,14,21H,5,8,13,15-16H2,1H3,(H,31,41)(H,34,38)(H,39,40)(H4,29,30,32,35,36)

Standard InChI Key:  PSOYDVAAVKYPCH-UHFFFAOYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA356340

   2-[[4-[(2,4-Diaminopteridin-6-yl)methyl-methylamino]benzoyl]amino]-5-(phenylmethoxycarbonylamino)pentanoic 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: 573.61

Molecular Weight (Monoisotopic): 573.2448

AlogP: 2.11

#Rotatable Bonds: 12

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: 3.47

CX Basic pKa: 2.87

CX LogP: 1.78

CX LogD: -1.45

Aromatic Rings: 4

Heavy Atoms: 42

QED Weighted: 0.15

Np Likeness Score: -0.68

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]

Source

Source(1):

• Scientific Literature