(2S,2'S)-2,2'-thiocarbonylbis(azanediyl)dipentanedioic acid

ID: ALA4870708

PubChem CID: 88900290

Max Phase: Preclinical

Molecular Formula: C11H16N2O8S

Molecular Weight: 336.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@H](NC(=S)N[C@@H](CCC(=O)O)C(=O)O)C(=O)O

Standard InChI:  InChI=1S/C11H16N2O8S/c14-7(15)3-1-5(9(18)19)12-11(22)13-6(10(20)21)2-4-8(16)17/h5-6H,1-4H2,(H,14,15)(H,16,17)(H,18,19)(H,20,21)(H2,12,13,22)/t5-,6-/m0/s1

Standard InChI Key:  LLFVSSPVFBEUOJ-WDSKDSINSA-N

Molfile:  

 
     RDKit          2D

 22 21  0  0  0  0  0  0  0  0999 V2000
   18.0731   -4.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7808   -3.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3654   -3.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.0731   -4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4886   -4.0736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1963   -3.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9040   -4.0736    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1963   -2.8478    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.6117   -3.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3194   -4.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0271   -3.6650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3194   -4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6117   -2.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7808   -2.8478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3194   -2.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3194   -1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0271   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6117   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4885   -2.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4885   -1.6220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1963   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7808   -1.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  3  1  0
  1  4  2  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  9 13  1  1
  2 14  1  6
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870708

   (2S)-2-[[(1S)-1,3-dicarboxypropyl]carbamothioylamino]pentanedioic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 336.32

Molecular Weight (Monoisotopic): 336.0627

AlogP: -0.91

#Rotatable Bonds: 10

Polar Surface Area: 173.26

Molecular Species: ACID

HBA: 5

HBD: 6

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.09

CX Basic pKa: ┄

CX LogP: -0.64

CX LogD: -13.28

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.27

Np Likeness Score: 0.06

References

1. Young JD, Ma MT, Eykyn TR, Atkinson RA, Abbate V, Cilibrizzi A, Hider RC, Blower PJ..  (2021)  Dipeptide inhibitors of the prostate specific membrane antigen (PSMA): A comparison of urea and thiourea derivatives.,  42  [PMID:33865971] [10.1016/j.bmcl.2021.128044]

Source

Source(1):

• Scientific Literature