2-amino-2-(hydroxymethyl)propane-1,3-diol; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid

• ChemBase ID: 155145
• Molecular Formular: C24H45NO8
• Molecular Mass: 475.616
• Monoisotopic Mass: 475.31451741
• SMILES: CCCCC[C@@H](C=C[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C/CCCC(=O)O)O)O)O.C(C(CO)(CO)N)O
• Canonical SMILES: OCC(CO)(CO)N.CCCCC[C@@H](C=C[C@H]1[C@H](O)C[C@@H]([C@@H]1C/C=C/CCCC(=O)O)O)O
• InChI: InChI=1S/C20H34O5.C4H11NO3/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;5-4(1-6,2-7)3-8/h4,7,12-13,15-19,21-23H,2-3,5-6,8-11,14H2,1H3,(H,24,25);6-8H,1-3,5H2/t15-,16+,17+,18-,19+;/m0./s1
• InChIKey: IYGXEHDCSOYNKY-NULUWHCBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-2-(hydroxymethyl)propane-1,3-diol; 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid
• IUPAC Traditional name: 7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid; tris buffer
• Synonyms: (5Z,9α,11α,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dienoic acid tris salt; PGF2α-Tris; Prostaglandin F2α tris salt

Database IDs

• CAS Number: 38562-01-5
• EC Number: 254-002-3
• MDL Number: MFCD00077863
• Beilstein Number: 4087514
• PubChem SID: 24898103; 162249283; 24898587
• PubChem CID: 71312085

CALCULATED PROPERTIES

• Acid pKa: 4.355294
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 1.4380769
• LogD (pH = 7.4): -0.31100234
• Log P: 2.6110544
• Molar Refractivity: 100.4707 cm^3
• Polarizability: 38.732555 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: ethanol: soluble50 mg/mL; H2O: soluble1 mg/mL (Aqueous solutions are stable for 30 days at 2-8°C and for several months frozen at -0°C in single use aliquots. Avoid repeated freeze/thaw cycles.)
• Apperance: white powder

Safety Information

• RTECS: UK8025000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-22
• Safety Statements: 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

Product Information

• Purity: ≥99%
• Suitability: cell culture tested
• Biological Source: synthetic
• Empirical Formula (Hill Notation): C20H34O5 · C4H11NO3

DETAILS

Sigma Aldrich - P5069

Biochem/physiol Actions
Luteolytic prostaglandin that induces parturition. Potent vasoconstrictor of pulmonary, coronary, and cerebral arteriole beds. A positive feedback loop between endometrial PG F2α and luteal oxytocin is responsible for completion of luteolysis.1
Luteolytic prostaglandin that induces parturition. Potent vasoconstrictor of pulmonary, coronary, and cerebral arteriole beds. Also stimulates contraction of smooth muscle, such as in bronchi, with possible involvement in asthma. This effect is at least partially mediated through tachykinin release.
Prostaglandin F2α is induced by uterine-produced oxytocin and acts on the corpus luteum to cause luteolysis and inhibit progesterone production.

Sigma Aldrich - P0424

Biochem/physiol Actions
Luteolytic prostaglandin that induces parturition. Potent vasoconstrictor of pulmonary, coronary, and cerebral arteriole beds. A positive feedback loop between endometrial PG F2α and luteal oxytocin is responsible for completion of luteolysis.1
Luteolytic prostaglandin that induces parturition. Potent vasoconstrictor of pulmonary, coronary, and cerebral arteriole beds. Also stimulates contraction of smooth muscle, such as in bronchi, with possible involvement in asthma. This effect is at least partially mediated through tachykinin release.