(2S,3S,4R)-4-Amino-2-tetradecyltetrahydrofuran-3-ol

ID: ALA1819205

Chembl Id: CHEMBL1819205

PubChem CID: 53494962

Max Phase: Preclinical

Molecular Formula: C18H37NO2

Molecular Weight: 299.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCC[C@@H]1OC[C@@H](N)[C@@H]1O

Standard InChI:  InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-17-18(20)16(19)15-21-17/h16-18,20H,2-15,19H2,1H3/t16-,17+,18+/m1/s1

Standard InChI Key:  FBQCDJRSCUVUFL-SQNIBIBYSA-N

Alternative Forms

1. Parent:

   

   ALA1819205

   (2S,3S,4R)-4-amino-2-tetradecyloxolan-3-ol

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: 299.50

Molecular Weight (Monoisotopic): 299.2824

AlogP: 4.16

#Rotatable Bonds: 13

Polar Surface Area: 55.48

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.55

CX Basic pKa: 9.10

CX LogP: 4.86

CX LogD: 3.17

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.50

Np Likeness Score: 1.04

References

1. Yoshimitsu Y, Oishi S, Miyagaki J, Inuki S, Ohno H, Fujii N..  (2011)  Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C.,  19  (18): [PMID:21868240] [10.1016/j.bmc.2011.07.061]

2. Ohno H, Honda M, Hamada N, Miyagaki J, Iwata A, Otsuki K, Maruyama T, Nakamura S, Nakanishi I, Inuki S, Fujii N, Oishi S..  (2017)  Identification of selective inhibitors of sphingosine kinases 1 and 2 through a structure-activity relationship study of 4-epi-jaspine B.,  25  (12): [PMID:28408190] [10.1016/j.bmc.2017.03.059]

3. Ding T, Zhi Y, Xie W, Yao Q, Liu B..  (2021)  Rational design of SphK inhibitors using crystal structures aided by computer.,  213  [PMID:33454547] [10.1016/j.ejmech.2021.113164]

Source

Source(1):

• Scientific Literature