S-Decyl-glutathione

ID: ALA2074814

Cas Number: 102814-04-0

PubChem CID: 443116

Max Phase: Preclinical

Molecular Formula: C20H37N3O6S

Molecular Weight: 447.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCSC[C@H](NC(=O)CC[C@H](N)C(=O)O)C(=O)NCC(=O)O

Standard InChI:  InChI=1S/C20H37N3O6S/c1-2-3-4-5-6-7-8-9-12-30-14-16(19(27)22-13-18(25)26)23-17(24)11-10-15(21)20(28)29/h15-16H,2-14,21H2,1H3,(H,22,27)(H,23,24)(H,25,26)(H,28,29)/t15-,16-/m0/s1

Standard InChI Key:  XAAOGZMKEJNHLW-HOTGVXAUSA-N

Molfile:  

     RDKit          2D

 30 29  0  0  1  0  0  0  0  0999 V2000
    8.4711    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1855    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9000    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6145    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3289    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0434    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7579    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4724    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1868    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9013    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6158    5.7158    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    6.1283    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9026    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.1283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6171    6.9533    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0460    6.1283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3315    4.8908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0447    4.8908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3302    4.4783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    4.4783    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7592    3.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    3.2408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881    3.6533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4737    2.4158    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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 21 23  2  0
 13 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA2074814

   S-Decylglutathione

Molecule Features

Natural Product: Yes

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: 447.60

Molecular Weight (Monoisotopic): 447.2403

AlogP: 1.74

#Rotatable Bonds: 19

Polar Surface Area: 158.82

Molecular Species: ZWITTERION

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.81

CX Basic pKa: 9.31

CX LogP: -0.60

CX LogD: -3.80

Aromatic Rings: ┄

Heavy Atoms: 30

QED Weighted: 0.19

Np Likeness Score: 0.27

References

1. Hagmann W, Nies AT, König J, Frey M, Zentgraf H, Keppler D..  (1999)  Purification of the human apical conjugate export pump MRP2 reconstitution and functional characterization as substrate-stimulated ATPase.,  265  (1): [PMID:10491184] [10.1046/j.1432-1327.1999.00735.x]

2. Leier I, Jedlitschky G, Buchholz U, Center M, Cole SP, Deeley RG, Keppler D..  (1996)  ATP-dependent glutathione disulphide transport mediated by the MRP gene-encoded conjugate export pump.,  314  (1): [PMID:8670053] [10.1042/bj3140433]

3. Jedlitschky, G G and 5 more authors.  1997-10-01  ATP-dependent transport of bilirubin glucuronides by the multidrug resistance protein MRP1 and its hepatocyte canalicular isoform MRP2.  [PMID:9355767]

Source

Source(1):

• TP-search Transporter Database