(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-N-octylcyclohex-2-enaminium chloride

ID: ALA1922580

PubChem CID: 54764418

Max Phase: Preclinical

Molecular Formula: C15H30ClNO4

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.Cl

Standard InChI:  InChI=1S/C15H29NO4.ClH/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;1H/t12-,13-,14+,15+;/m1./s1

Standard InChI Key:  MPYFYLDLOZTRGL-JMOBQWKXSA-N

Molfile:  

     RDKit          2D

 21 20  0  0  0  0  0  0  0  0999 V2000
    9.2750    0.4375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1083    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1083   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5324   -0.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5324    0.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204    1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5348    1.9875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3927    0.7437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3945   -0.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8204   -1.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2462   -0.9052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9613   -0.4937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6752   -0.9073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3903   -0.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1041   -0.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8192   -0.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5331   -0.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2481   -0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9620   -0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3 11  1  1
  3  4  1  0
  4 12  1  6
  4  5  1  0
  5 13  1  1
  5  6  1  0
 13 14  1  0
  6  7  2  0
 14 15  1  0
 15 16  1  0
  7  8  1  0
 16 17  1  0
 17 18  1  0
  8  9  1  0
 18 19  1  0
  2  3  1  0
 19 20  1  0
  2 10  1  6
 20 21  1  0
  2  7  1  0
M  END

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]

Source

Source(1):

• Scientific Literature