N-octyl-4-epi-beta-valienamine

ID: ALA1922581

PubChem CID: 10039700

Max Phase: Preclinical

Molecular Formula: C15H29NO4

Molecular Weight: 287.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCN[C@@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H29NO4/c1-2-3-4-5-6-7-8-16-12-9-11(10-17)13(18)15(20)14(12)19/h9,12-20H,2-8,10H2,1H3/t12-,13+,14+,15+/m1/s1

Standard InChI Key:  UPZUHYMBTUUPML-QPSCCSFWSA-N

Molfile:  

     RDKit          2D

 20 20  0  0  0  0  0  0  0  0999 V2000
   -3.5792    0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5792   -0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -0.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1551   -0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1551    0.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671    1.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1527    2.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2948    0.8396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2930   -0.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8671   -1.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4413   -0.8094    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7262   -0.3979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0123   -0.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7028   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4166   -0.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1317   -0.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8456   -0.8156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5606   -0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2745   -0.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  1
  2  3  1  0
  3 11  1  6
  3  4  1  0
  4 12  1  1
  4  5  1  0
 12 13  1  0
  5  6  2  0
 13 14  1  0
 14 15  1  0
  6  7  1  0
 15 16  1  0
 16 17  1  0
  7  8  1  0
 17 18  1  0
  1  2  1  0
 18 19  1  0
  1  9  1  1
 19 20  1  0
  1  6  1  0
M  END

Alternative Forms

1. Alternative Forms:

   

   ALA1922581

   (1S,2S,3S,6R)-4-(hydroxymethyl)-6-(octylamino)cyclohex-4-ene-1,2,3-triol;hydrochloride

2. Parent:

   

   ALA1922581

   (1s,2s,3s,6r)-4-(Hydroxymethyl)-6-(Octylamino)cyclohex-4-Ene-1,2,3-Triol

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: 287.40

Molecular Weight (Monoisotopic): 287.2097

AlogP: 0.32

#Rotatable Bonds: 9

Polar Surface Area: 92.95

Molecular Species: NEUTRAL

HBA: 5

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.83

CX Basic pKa: 8.47

CX LogP: 0.40

CX LogD: -0.70

Aromatic Rings: ┄

Heavy Atoms: 20

QED Weighted: 0.31

Np Likeness Score: 1.50

References

1. Kuno S, Takahashi A, Ogawa S..  (2011)  Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV).,  21  (23): [PMID:22001090] [10.1016/j.bmcl.2011.09.067]

2. Boyd RE, Lee G, Rybczynski P, Benjamin ER, Khanna R, Wustman BA, Valenzano KJ..  (2013)  Pharmacological chaperones as therapeutics for lysosomal storage diseases.,  56  (7): [PMID:23363020] [10.1021/jm301557k]

3. Thonhofer M, Weber P, Santana AG, Fischer R, Pabst BM, Paschke E, Schalli M, Stütz AE, Tschernutter M, Windischhofer W, Withers SG..  (2016)  Synthesis of C-5a-chain extended derivatives of 4-epi-isofagomine: Powerful β-galactosidase inhibitors and low concentration activators of GM1-gangliosidosis-related human lysosomal β-galactosidase.,  26  (5): [PMID:26838810] [10.1016/j.bmcl.2016.01.059]

4. Schalli M, Weber P, Tysoe C, Pabst BM, Thonhofer M, Paschke E, Stütz AE, Tschernutter M, Windischhofer W, Withers SG..  (2017)  A new type of pharmacological chaperone for GM1-gangliosidosis related human lysosomal β-galactosidase: N-Substituted 5-amino-1-hydroxymethyl-cyclopentanetriols.,  27  (15): [PMID:28600215] [10.1016/j.bmcl.2017.05.086]

Source

Source(1):

• Scientific Literature