(S)-2-[4-((1R,2S)-2-Hydroxy-cyclopentylmethyl)-phenyl]-propionic acid

ID: ALA441414

Chembl Id: CHEMBL441414

Cas Number: 83648-76-4

PubChem CID: 10037656

Max Phase: Unknown

Molecular Formula: C15H20O3

Molecular Weight: 248.32

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Loxoprofen trans alcohol | Loxoprofen srs|loxoprofen active metabolite|Loxoprofenol-SRS|UNII-926CB5J9Z0|83648-76-4|Loxoprofen-(2S,1'R,2'S)-trans-alcohol|926CB5J9Z0|Loxoprofen trans-alcohol, (2S,1'R,2'S)-|HR1405-01|CHEMBL441414|CHEBI:76204|Benzeneacetic acid, 4-(((1R,2S)-2-hydroxycyclopentyl)methyl)-alpha-methyl-, (alphaS)-|Benzeneacetic acid, 4-(((1R,2S)-2-hydroxycyclopentyl)methyl)-alpha-methyl-, rel-|loxoprofen-SRS|Loxoprofen metabolite|loxoprofen trans-alcohol|Loxoprofen trans alcohol|SCHEMBLShow More⌵

Canonical SMILES:  C[C@H](C(=O)O)c1ccc(C[C@H]2CCC[C@@H]2O)cc1

Standard InChI:  InChI=1S/C15H20O3/c1-10(15(17)18)12-7-5-11(6-8-12)9-13-3-2-4-14(13)16/h5-8,10,13-14,16H,2-4,9H2,1H3,(H,17,18)/t10-,13+,14-/m0/s1

Standard InChI Key:  SHAHPWSYJFYMRX-GDLCADMTSA-N

Alternative Forms

1. Parent:

   

   ALA441414

   LOXOPROFEN TRANS ALCOHOL

2. Alternative Forms:

   

   ALA441414

   ---

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: 248.32

Molecular Weight (Monoisotopic): 248.1412

AlogP: 2.58

#Rotatable Bonds: 4

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.28

CX Basic pKa:

CX LogP: 2.96

CX LogD: -0.02

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.86

Np Likeness Score: 0.92

References

1. Riendeau D, Salem M, Styhler A, Ouellet M, Mancini JA, Li CS..  (2004)  Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2.,  14  (5): [PMID:14980665] [10.1016/j.bmcl.2003.12.047]

2. Unpublished dataset, 

3. Ye H, Lv T, Min T, Mao D, Chen X, Ding B, Zhang C..  (2022)  HR1405-01, a Safe intravenous NSAID with superior anti-inflammatory and analgesic activities in preclinical trials.,  235  [PMID:35339101] [10.1016/j.ejmech.2022.114258]

Source

Source(2):

• Scientific Literature
• Active Ingredient of a Prodrug