propan-2-yl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate

• ChemBase ID: 153761
• Molecular Formular: C26H40O5
• Molecular Mass: 432.5928
• Monoisotopic Mass: 432.28757438
• SMILES: CC(C)OC(=O)CCC/C=C/C[C@H]1[C@H](C[C@H]([C@@H]1CC[C@@H](CCc1ccccc1)O)O)O
• Canonical SMILES: O[C@H](CCc1ccccc1)CC[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C/CCCC(=O)OC(C)C)O
• InChI: InChI=1S/C26H40O5/c1-19(2)31-26(30)13-9-4-3-8-12-22-23(25(29)18-24(22)28)17-16-21(27)15-14-20-10-6-5-7-11-20/h3,5-8,10-11,19,21-25,27-29H,4,9,12-18H2,1-2H3/t21-,22-,23-,24+,25-/m1/s1
• InChIKey: GGXICVAJURFBLW-UUFXTFJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: propan-2-yl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; propan-2-yl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• IUPAC Traditional name: isopropyl (5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate; isopropyl 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
• Synonyms: (5E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoic Acid 1-Methylethyl Ester; Isoproyl (E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(3S)-3-hydroxy-5-phenylpentyl]cyclopentyl]-5-heptenoate; (5E,15S)-Latanoprost; 5,6-trans-(15S)-Latanoprost; trans-(15S)-Latanoprost; (5Z,9α,11α,15S)-9,11,15-Trihydroxy-17-phenyl-18,19,20-trinor-prost-5-en-1-oate isopropyl ester; 15(S)-Latanoprost solution

Database IDs

• CAS Number: 1235141-39-5
• EC Number: 201-185-2
• MDL Number: MFCD04974500
• PubChem SID: 162247900
• PubChem CID: 52193982

CALCULATED PROPERTIES

• Acid pKa: 14.468507
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 3.9810123
• LogD (pH = 7.4): 3.9810123
• Log P: 3.9810123
• Molar Refractivity: 124.3376 cm^3
• Polarizability: 48.735634 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Flash Point: -16 °C; 3.2 °F

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1231
• German water hazard class: 2
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-36-66-67
• Safety Statements: 16-26-29-33
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H319-H336
• GHS Precautionary statements: P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1231 3/PG 2
• Supplemental Hazard Statements: Repeated exposure may cause skin dryness or cracking.
• Storage Temperature: -20°C

Product Information

• Purity: ≥95%
• Concentration: 10 mg/mL in methyl acetate
• Empirical Formula (Hill Notation): C26H40O5

DETAILS

Sigma Aldrich - L1417

Linkage
15(S)-Latanoprost is the less active C-15 isomer of latanoprost where the C-15 hydroxyl group is inverted relative to its natural (α) position in a prostaglandin such as PGF2α. The 15(S)-isomer of latanoprost occurs as an impurity of between 0.1 and 1% in most commercial preparations of latanoprost.

Toronto Research Chemicals - L177305

Latanoprost analog.