(4R,5S,6E)-5-[2-Amino-2-(carboxymethyl-carbamoyl)-ethylsulfanyl]-4-hydroxy-nonadec-6-enoic acid. 7/8H2O

ID: ALA3707134

PubChem CID: 101613123

Max Phase: Preclinical

Molecular Formula: C24H44N2O6S

Molecular Weight: 488.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCC/C=C/[C@H](SC[C@H](N)C(=O)NCC(=O)O)[C@@H](O)CCC(=O)O

Standard InChI:  InChI=1S/C24H44N2O6S/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-21(20(27)15-16-22(28)29)33-18-19(25)24(32)26-17-23(30)31/h13-14,19-21,27H,2-12,15-18,25H2,1H3,(H,26,32)(H,28,29)(H,30,31)/b14-13+/t19-,20-,21-/m0/s1

Standard InChI Key:  GAXVUDYIUJUDBE-XHTVIRLASA-N

Molfile:  

     RDKit          2D

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   12.0236   -4.7734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3349   -4.2056    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0898   -6.4768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2702  -13.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7620  -12.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7620   -9.3158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0898  -10.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5980  -10.7353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9259  -11.4924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4341  -12.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9259   -7.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2537   -8.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5980  -14.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  7  1  0
  5 13  1  0
  6 18  1  0
  7  2  1  0
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  9  6  2  0
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 11  4  1  1
 12 11  1  0
 13  3  1  0
 14 12  2  0
 15 17  1  0
  2 16  1  1
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 17 21  1  6
 22 14  1  0
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 24 25  1  0
 25 30  1  0
 26 32  1  0
 27 26  1  0
 28 27  1  0
 29 28  1  0
 30 29  1  0
 31 23  1  0
 32 31  1  0
 33 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3707134

   (E,4S,5S)-5-[(2R)-2-amino-3-(carboxymethylamino)-3-oxopropyl]sulfanyl-4-hydroxynonadec-6-enoic 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: 488.69

Molecular Weight (Monoisotopic): 488.2920

AlogP: 3.71

#Rotatable Bonds: 22

Polar Surface Area: 149.95

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.58

CX Basic pKa: 8.05

CX LogP: 1.38

CX LogD: -1.51

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.11

Np Likeness Score: 0.93

References

1. Ku TW, McCarthy ME, Weichman BM, Gleason JG..  (1985)  Synthesis and LTD4 antagonist activity of 2-norleukotriene analogues.,  28  (12): [PMID:4068008] [10.1021/jm00150a016]

Source

Source(1):

• Scientific Literature