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

ID: ALA447577

Chembl Id: CHEMBL447577

PubChem CID: 9814817

Max Phase: Preclinical

Molecular Formula: C18H37NO2

Molecular Weight: 299.50

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Pachastrissamine | PACHASTRISSAMINE|SCHEMBL766801|CHEMBL447577|(2S,3S,4S)-4-amino-2-tetradecyloxolan-3-ol

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-/m0/s1

Standard InChI Key:  FBQCDJRSCUVUFL-BZSNNMDCSA-N

Alternative Forms

1. Parent:

   

   ALA447577

   PACHASTRISSAMINE

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. Canals D, Mormeneo D, Fabriàs G, Llebaria A, Casas J, Delgado A..  (2009)  Synthesis and biological properties of Pachastrissamine (jaspine B) and diastereoisomeric jaspines.,  17  (1): [PMID:19056278] [10.1016/j.bmc.2008.11.026]

2. Kuroda I, Musman M, Ohtani II, Ichiba T, Tanaka J, Gravalos DG, Higa T..  (2002)  Pachastrissamine, a cytotoxic anhydrophytosphingosine from a marine sponge, Pachastrissa sp.,  65  (10): [PMID:12398554] [10.1021/np010659y]

3. 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]

4. Xu JM, Zhang E, Shi XJ, Wang YC, Yu B, Jiao WW, Guo YZ, Liu HM..  (2014)  Synthesis and preliminary biological evaluation of 1,2,3-triazole-Jaspine B hybrids as potential cytotoxic agents.,  80  [PMID:24835817] [10.1016/j.ejmech.2014.03.022]

5. Zhang E, Wang S, Li LL, Hua YG, Yue JF, Li JF, Jin CY..  (2018)  Discovery of novel jaspine B analogues as autophagy inducer.,  28  (3): [PMID:29254641] [10.1016/j.bmcl.2017.12.011]

6. 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