4-(Carboxymethyl-carbamoyl)-4-{[1-(2-{2-[(9,10-dioxo-9,10-dihydro-phenanthrene-2-carbonyl)-amino]-acetylamino}-5-guanidino-pentanoyl)-pyrrolidine-2-carbonyl]-amino}-butyric acid

ID: ALA2372875

PubChem CID: 10628864

Max Phase: Preclinical

Molecular Formula: C35H40N8O11

Molecular Weight: 748.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N=C(N)NCCC[C@H](NC(=O)CNC(=O)c1ccc2c(c1)C(=O)C(=O)c1ccccc1-2)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)O)C(=O)NCC(=O)O

Standard InChI:  InChI=1S/C35H40N8O11/c36-35(37)38-13-3-7-24(34(54)43-14-4-8-25(43)33(53)42-23(11-12-27(45)46)32(52)40-17-28(47)48)41-26(44)16-39-31(51)18-9-10-20-19-5-1-2-6-21(19)29(49)30(50)22(20)15-18/h1-2,5-6,9-10,15,23-25H,3-4,7-8,11-14,16-17H2,(H,39,51)(H,40,52)(H,41,44)(H,42,53)(H,45,46)(H,47,48)(H4,36,37,38)/t23-,24-,25-/m0/s1

Standard InChI Key:  FWQJLERQQBQSLM-SDHOMARFSA-N

Molfile:  

     RDKit          2D

 54 57  0  0  0  0  0  0  0  0999 V2000
    3.5655   -3.5488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5696   -3.4780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2819   -3.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9983   -3.4406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8533   -3.1407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5946   -4.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3028   -2.2992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0191   -4.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3319   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2736   -3.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8574   -3.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0275   -1.9119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370   -3.1115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4521   -1.7911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7498   -6.8769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1576   -3.5030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1410   -3.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4162   -3.1532    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8948   -4.7276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7773   -2.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6998   -3.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7331   -3.5363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1893   -2.1618    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4662   -7.2851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6138   -2.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6645   -4.2528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444   -2.2118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7064   -3.0115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8408   -2.3159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6030   -1.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1743   -4.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4203   -2.2867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4271   -0.9372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6873   -4.3777    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6638   -2.8990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897   -4.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8481   -3.0865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7373   -6.0522    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083   -3.1282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8766   -1.7036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417   -7.3018    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7655   -4.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5895   -3.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4100   -4.6027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3011   -1.6162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7564   -4.6734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3444   -5.5399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9026   -3.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5985   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4495   -5.6273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4412   -4.8026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0691   -5.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7689   -5.4982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 11  1  0
  3  2  1  0
  4  3  1  0
  5  1  1  0
  6 19  1  0
 10  7  1  6
  8  9  2  0
  9  6  1  0
 10  1  1  0
 11 16  2  0
 12  7  1  0
 13 22  1  0
 14 20  1  0
 15 38  1  0
 16 13  1  0
 17  5  1  0
 18 17  1  0
 19 31  2  0
 20 12  1  0
 21 18  1  0
 22 39  1  0
 23 14  1  0
 24 15  2  0
 25 40  1  0
 26 43  1  0
 27  3  2  0
 28  4  2  0
 29  5  2  0
 30  7  2  0
 31 16  1  0
 32 13  2  0
 33 14  2  0
 34 21  2  0
 35 25  2  0
 36 26  2  0
 20 37  1  6
 38 51  1  0
 39 21  1  0
 40 23  1  0
 41 15  1  0
 42  1  1  0
 43 37  1  0
 44 26  1  0
 45 25  1  0
 46  8  1  0
 47  9  1  0
 48 10  1  0
 49 42  1  0
 17 50  1  6
 51 52  1  0
 52 50  1  0
 53 47  2  0
 54 53  1  0
 49 48  1  0
  6  2  2  0
  4  8  1  0
 46 54  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2372875

   (4S)-5-(carboxymethylamino)-4-[[(2S)-1-[(2S)-5-(diaminomethylideneamino)-2-[[2-[(9,10-dioxophenanthrene-2-carbonyl)amino]acetyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-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: 748.75

Molecular Weight (Monoisotopic): 748.2817

AlogP: -1.25

#Rotatable Bonds: 17

Polar Surface Area: 307.35

Molecular Species: ZWITTERION

HBA: 10

HBD: 9

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.35

CX Basic pKa: 12.09

CX LogP: -4.14

CX LogD: -7.16

Aromatic Rings: 2

Heavy Atoms: 54

QED Weighted: 0.04

Np Likeness Score: -0.20

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