2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid

• ChemBase ID: 178843
• Molecular Formular: C23H34O5
• Molecular Mass: 390.51306
• Monoisotopic Mass: 390.24062419
• SMILES: [C@H]12[C@H](Cc3c(C1)c(ccc3)OCC(=O)O)[C@H]([C@@H](C2)O)CC[C@H](CCCCC)O
• Canonical SMILES: CCCCC[C@@H](CC[C@H]1[C@H](O)C[C@H]2[C@@H]1Cc1cccc(c1C2)OCC(=O)O)O
• InChI: InChI=1S/C23H34O5/c1-2-3-4-7-17(24)9-10-18-19-11-15-6-5-8-22(28-14-23(26)27)20(15)12-16(19)13-21(18)25/h5-6,8,16-19,21,24-25H,2-4,7,9-14H2,1H3,(H,26,27)/t16-,17-,18+,19-,21+/m0/s1
• InChIKey: PAJMKGZZBBTTOY-ZFORQUDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(1R,2R,3aS,9aS)-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H,2H,3H,3aH,4H,9H,9aH-cyclopenta[b]naphthalen-5-yl]oxy}acetic acid
• IUPAC Traditional name: treprostinil
• Synonyms: 2-[[(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-Hexahydro-2-hydroxy-1-[(3S)-3-hydroxyoctyl]-1H-benz[f]inden-5-yl]oxy]acetic Acid; [1R-[1α(S*),2β,3aα,9aα]]-[[2,3,3a,4,9,9a-Ηexahydro-2-hydroxy-1-(3-hydroxyoctyl)-1H-benz[f]inden-5-yl]oxy]acetic Acid; 15AU81; BW 15AU; LRX 15; U 62840; Uniprost; Treprostinil

Database IDs

• CAS Number: 81846-19-7
• PubChem SID: 164234753
• PubChem CID: 6918140

CALCULATED PROPERTIES

• Acid pKa: 3.760436
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.2637904
• LogD (pH = 7.4): 0.7241018
• Log P: 4.0042095
• Molar Refractivity: 108.0016 cm^3
• Polarizability: 42.45696 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T719500

Synthetic analog of Prostacyclin (P839060). Antihypertensive. Treprostinil, marketed under the trade name Remodulin is a medication used to treat pulmonary arterial hypertension (PAH).

REFERENCES

• Laliberte, K., et al.: J. Cardiovasc. Pharmacol., 44, 209 (2004)