5-{2-[3-Carboxy-1-(carboxymethyl-carbamoyl)-propylcarbamoyl]-pyrrolidin-1-yl}-4-{2-[(9,10-dioxo-9,10-dihydro-phenanthrene-2-carbonyl)-amino]-acetylamino}-5-oxo-pentanoic acid

ID: ALA2372892

PubChem CID: 10818644

Max Phase: Preclinical

Molecular Formula: C34H35N5O13

Molecular Weight: 721.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CCC(=O)O)NC(=O)CNC(=O)c1ccc2c(c1)C(=O)C(=O)c1ccccc1-2)C(=O)NCC(=O)O

Standard InChI:  InChI=1S/C34H35N5O13/c40-25(15-35-31(49)17-7-8-19-18-4-1-2-5-20(18)29(47)30(48)21(19)14-17)37-23(10-12-27(43)44)34(52)39-13-3-6-24(39)33(51)38-22(9-11-26(41)42)32(50)36-16-28(45)46/h1-2,4-5,7-8,14,22-24H,3,6,9-13,15-16H2,(H,35,49)(H,36,50)(H,37,40)(H,38,51)(H,41,42)(H,43,44)(H,45,46)/t22-,23-,24-/m0/s1

Standard InChI Key:  VBKWFVJBVAGRSM-HJOGWXRNSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA2372892

   (4S)-4-[[(2S)-1-[(2S)-4-carboxy-2-[[2-[(9,10-dioxophenanthrene-2-carbonyl)amino]acetyl]amino]butanoyl]pyrrolidine-2-carbonyl]amino]-5-(carboxymethylamino)-5-oxopentanoic 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: 721.68

Molecular Weight (Monoisotopic): 721.2231

AlogP: -0.65

#Rotatable Bonds: 16

Polar Surface Area: 282.75

Molecular Species: ACID

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.25

CX Basic pKa: ┄

CX LogP: -1.68

CX LogD: -11.37

Aromatic Rings: 2

Heavy Atoms: 52

QED Weighted: 0.11

Np Likeness Score: -0.30

References

1. Urbanek RA, Suchard SJ, Steelman GB, Knappenberger KS, Sygowski LA, Veale CA, Chapdelaine MJ..  (2001)  Potent reversible inhibitors of the protein tyrosine phosphatase CD45.,  44  (11): [PMID:11356112] [10.1021/jm000447i]

Source

Source(1):

• Scientific Literature