(2S,23S)-2,23-diamino-5,10,15,20-tetraoxo-13-(phenethylamino)-11-oxa-6,12,14,19-tetraazatetracos-12-ene-1,24-dioic acid

ID: ALA2398470

PubChem CID: 73355045

Max Phase: Preclinical

Molecular Formula: C27H41N7O9

Molecular Weight: 607.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CCC(=O)NCCCC(=O)N/C(=N\OC(=O)CCCNC(=O)CC[C@H](N)C(=O)O)NCCc1ccccc1)C(=O)O

Standard InChI:  InChI=1S/C27H41N7O9/c28-19(25(39)40)10-12-21(35)30-15-4-8-23(37)33-27(32-17-14-18-6-2-1-3-7-18)34-43-24(38)9-5-16-31-22(36)13-11-20(29)26(41)42/h1-3,6-7,19-20H,4-5,8-17,28-29H2,(H,30,35)(H,31,36)(H,39,40)(H,41,42)(H2,32,33,34,37)/t19-,20-/m0/s1

Standard InChI Key:  AYFYXCQBCUCYJB-PMACEKPBSA-N

Molfile:  

     RDKit          2D

 43 43  0  0  0  0  0  0  0  0999 V2000
   28.4439  -21.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1584  -21.5548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.8591  -21.9753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5736  -21.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2743  -21.9991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5874  -20.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3003  -20.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.8851  -20.3400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7432  -21.5309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4301  -22.7685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0287  -21.9275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3280  -21.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6135  -21.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9128  -21.4832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9265  -20.6661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1983  -21.8798    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.4975  -21.4593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7830  -21.8559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5113  -20.6423    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0823  -21.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3678  -21.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6671  -21.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6857  -20.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9858  -20.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2703  -20.5734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2591  -21.3948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9596  -21.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2258  -20.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2396  -19.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9541  -19.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5389  -19.0081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6548  -19.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3693  -19.0558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0700  -19.4763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7845  -19.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4853  -19.5002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7983  -18.2626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1997  -19.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2135  -18.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9280  -17.8899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5128  -17.8660    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6307  -18.3099    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9438  -17.0724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  1
  6  7  1  0
  6  8  2  0
  1  9  1  0
  1 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 19 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 30 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 35 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  1  0
 39 41  1  6
 40 42  1  0
 40 43  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2398470

   (2S)-2-amino-5-[[4-[[N-[4-[[(4S)-4-amino-4-carboxybutanoyl]amino]butanoyloxy]-N'-(2-phenylethyl)carbamimidoyl]amino]-4-oxobutyl]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: 607.67

Molecular Weight (Monoisotopic): 607.2966

AlogP: -1.07

#Rotatable Bonds: 20

Polar Surface Area: 264.63

Molecular Species: ZWITTERION

HBA: 10

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.99

CX Basic pKa: 9.59

CX LogP: -5.98

CX LogD: -5.99

Aromatic Rings: 1

Heavy Atoms: 43

QED Weighted: 0.03

Np Likeness Score: -0.22

References

1. Zhang Q, Milliken P, Kulczynska A, Slawin AM, Gordon A, Kirkby NS, Webb DJ, Botting NP, Megson IL..  (2013)  Development and characterization of glutamyl-protected N-hydroxyguanidines as reno-active nitric oxide donor drugs with therapeutic potential in acute renal failure.,  56  (13): [PMID:23782349] [10.1021/jm400146r]

Source

Source(1):

• Scientific Literature