(S)-2-amino-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propane-1,3-diol

ID: ALA1090707

PubChem CID: 25192155

Max Phase: Preclinical

Molecular Formula: C21H35NO2

Molecular Weight: 333.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCc1ccc2c(c1)CC[C@H](C(N)(CO)CO)C2

Standard InChI:  InChI=1S/C21H35NO2/c1-2-3-4-5-6-7-8-17-9-10-19-14-20(12-11-18(19)13-17)21(22,15-23)16-24/h9-10,13,20,23-24H,2-8,11-12,14-16,22H2,1H3/t20-/m0/s1

Standard InChI Key:  FCWUGFDEMJLPMH-FQEVSTJZSA-N

Molfile:  

     RDKit          2D

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   -0.0943   -2.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6207   -2.9616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6189   -1.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3344   -1.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3332   -2.5508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0502   -2.9661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7731   -2.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7743   -1.7196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0526   -1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8085   -2.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211   -2.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2338   -2.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9464   -2.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6591   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3717   -2.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0844   -2.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7971   -2.5297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900   -1.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2035   -1.7231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9192   -1.3123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4920   -0.4836    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4841   -2.1338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1958   -2.5515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7673   -0.8919    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  1  0
  2  3  1  0
 12 13  1  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  1  0
  4  1  1  0
 16 17  1  0
  5 10  1  0
 17 18  1  0
  6  7  1  0
  9 19  1  0
  7  8  1  0
 19 20  1  0
  8  9  1  0
 20 21  1  0
  9 10  1  0
 19 22  1  0
  5  6  1  0
 19 23  1  0
  2 11  1  0
 23 24  1  0
  9 25  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA1090707

   2-amino-2-[(2S)-6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl]propane-1,3-diol

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: 333.52

Molecular Weight (Monoisotopic): 333.2668

AlogP: 3.38

#Rotatable Bonds: 10

Polar Surface Area: 66.48

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.44

CX LogP: 4.48

CX LogD: 2.47

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.58

Np Likeness Score: 0.40

References

1. Ma B, Guckian KM, Lin EY, Lee WC, Scott D, Kumaravel G, Macdonald TL, Lynch KR, Black C, Chollate S, Hahm K, Hetu G, Jin P, Luo Y, Rohde E, Rossomando A, Scannevin R, Wang J, Yang C..  (2010)  Stereochemistry-activity relationship of orally active tetralin S1P agonist prodrugs.,  20  (7): [PMID:20188554] [10.1016/j.bmcl.2010.02.006]

Source

Source(1):

• Scientific Literature