O-(Hydroxy(((2R,3R)-2-(((3-(2-(undecyloxy)phenyl)propanoyl)-oxy)methyl)tetrahydro-2H-pyran-3-yl)oxy)phosphoryl)-L-serine

ID: ALA3814763

PubChem CID: 78319747

Max Phase: Preclinical

Molecular Formula: C29H48NO10P

Molecular Weight: 601.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCOc1ccccc1CCC(=O)OC[C@H]1OCCC[C@H]1OP(=O)(O)OC[C@H](N)C(=O)O

Standard InChI:  InChI=1S/C29H48NO10P/c1-2-3-4-5-6-7-8-9-12-19-36-25-15-11-10-14-23(25)17-18-28(31)38-22-27-26(16-13-20-37-27)40-41(34,35)39-21-24(30)29(32)33/h10-11,14-15,24,26-27H,2-9,12-13,16-22,30H2,1H3,(H,32,33)(H,34,35)/t24-,26+,27+/m0/s1

Standard InChI Key:  LCQWPZMPNVZPDB-WYMJOSIYSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3814763

   (2S)-2-amino-3-[hydroxy-[(2R,3R)-2-[3-(2-undecoxyphenyl)propanoyloxymethyl]oxan-3-yl]oxyphosphoryl]oxypropanoic acid

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: 601.67

Molecular Weight (Monoisotopic): 601.3016

AlogP: 5.17

#Rotatable Bonds: 22

Polar Surface Area: 163.84

Molecular Species: ZWITTERION

HBA: 9

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.49

CX Basic pKa: 9.38

CX LogP: 3.80

CX LogD: 0.78

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.09

Np Likeness Score: 0.47

References

1. Jung S, Inoue A, Nakamura S, Kishi T, Uwamizu A, Sayama M, Ikubo M, Otani Y, Kano K, Makide K, Aoki J, Ohwada T..  (2016)  Conformational Constraint of the Glycerol Moiety of Lysophosphatidylserine Affords Compounds with Receptor Subtype Selectivity.,  59  (8): [PMID:27077565] [10.1021/acs.jmedchem.5b01925]

Source

Source(1):

• Scientific Literature