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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 14:58:44 UTC
HMDB IDHMDB0014792
Secondary Accession Numbers
  • HMDB14792
Metabolite Identification
Common NameLatanoprost
DescriptionLatanoprost, also known as xalatan or phxa 41, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Latanoprost is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582753221
Synonyms
ValueSource
Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoateChEBI
LatanoprostumChEBI
PhXA 41ChEBI
Propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoateChEBI
XalatanChEBI
Isopropyl (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((3R)-3-hydroxy-5-phenylpentyl)cyclopentyl)-5-heptenoic acidGenerator
Propan-2-yl (5Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoic acidGenerator
PHXA41HMDB
Pfizer brand OF latanoprostHMDB
PhXA34HMDB
Chemical FormulaC26H40O5
Average Molecular Weight432.5928
Monoisotopic Molecular Weight432.28757439
IUPAC Namepropan-2-yl (5Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl]hept-5-enoate
Traditional Namelatanoprost
CAS Registry Number130209-82-4
SMILES
CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1
InChI Identifier
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/b8-3-/t21-,22+,23+,24-,25+/m0/s1
InChI KeyGGXICVAJURFBLW-CEYXHVGTSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassEicosanoids
Direct ParentProstaglandins and related compounds
Alternative Parents
Substituents
  • Prostaglandin skeleton
  • Fatty acid ester
  • Monocyclic benzene moiety
  • Cyclopentanol
  • Benzenoid
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.013 g/LNot Available
LogP4.4Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP10(4.16) g/LALOGPS
logP10(3.98) g/LChemAxon
logS10(-4.5) g/LALOGPS
pKa (Strongest Acidic)14.47ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity124.34 m³·mol⁻¹ChemAxon
Polarizability50.71 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+206.51431661259
DarkChem[M-H]-198.65231661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LatanoprostCC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13853.6Standard polar33892256
LatanoprostCC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C12830.4Standard non polar33892256
LatanoprostCC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13437.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Latanoprost,1TMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13225.4Semi standard non polar33892256
Latanoprost,1TMS,isomer #2CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13235.7Semi standard non polar33892256
Latanoprost,1TMS,isomer #3CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C3308.4Semi standard non polar33892256
Latanoprost,2TMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13199.7Semi standard non polar33892256
Latanoprost,2TMS,isomer #2CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C3217.2Semi standard non polar33892256
Latanoprost,2TMS,isomer #3CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C3226.8Semi standard non polar33892256
Latanoprost,3TMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C3211.3Semi standard non polar33892256
Latanoprost,1TBDMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13444.5Semi standard non polar33892256
Latanoprost,1TBDMS,isomer #2CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13454.9Semi standard non polar33892256
Latanoprost,1TBDMS,isomer #3CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C3533.3Semi standard non polar33892256
Latanoprost,2TBDMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C13634.1Semi standard non polar33892256
Latanoprost,2TBDMS,isomer #2CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C3657.9Semi standard non polar33892256
Latanoprost,2TBDMS,isomer #3CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C3672.4Semi standard non polar33892256
Latanoprost,3TBDMS,isomer #1CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1CC[C@H](CCC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C3839.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Latanoprost GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-5469500000-3070e3312e2f54422eeb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Latanoprost GC-MS (3 TMS) - 70eV, Positivesplash10-001l-7110196000-109246e3e73496dba6fd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Latanoprost GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Latanoprost LC-ESI-qTof , Positive-QTOFsplash10-052r-1958000000-c694c9459db45a20b9af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Latanoprost , positive-QTOFsplash10-052r-1958000000-c694c9459db45a20b9af2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Latanoprost 35V, Positive-QTOFsplash10-053i-1944000000-f34558bc420a9182b5a72021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 10V, Positive-QTOFsplash10-014j-1019700000-ea3b09b676d18f1597e82016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 20V, Positive-QTOFsplash10-03di-5119100000-970c5bfecae331f192372016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 40V, Positive-QTOFsplash10-03dl-9123000000-71493bbb4b5c38c17db22016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 10V, Negative-QTOFsplash10-053r-3002900000-194e702a216b0d2dfe902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 20V, Negative-QTOFsplash10-0a4i-9104400000-d8c800c6e0be22ba0c3b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 40V, Negative-QTOFsplash10-0a4i-9001000000-d471d19421c5af96709a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 10V, Positive-QTOFsplash10-00kb-0009500000-d2a48aae87364fb994dd2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 20V, Positive-QTOFsplash10-00xs-1129200000-ed0b6de04b391bc1df9d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 40V, Positive-QTOFsplash10-052g-7900000000-8bffc330b362b9ac0f992021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 10V, Negative-QTOFsplash10-001i-0001900000-1b7b5dcba43a1725ab4f2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 20V, Negative-QTOFsplash10-05ai-1019400000-26284711fd786b2aa5922021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Latanoprost 40V, Negative-QTOFsplash10-0a4l-9521000000-3fb318e74064f7c258052021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00654 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00654 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00654
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4470740
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLatanoprost
METLIN IDNot Available
PubChem Compound5311221
PDB IDNot Available
ChEBI ID6384
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hara T: [Increased iris pigmentation after use of latanoprost in Japanese brown eyes]. Nippon Ganka Gakkai Zasshi. 2001 May;105(5):314-21. [PubMed:11406947 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  4. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  5. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Receptor for prostaglandin F2-alpha (PGF2-alpha). The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. Initiates luteolysis in the corpus luteum
Gene Name:
PTGFR
Uniprot ID:
P43088
Molecular weight:
40054.1
References
  1. Ota T, Aihara M, Narumiya S, Araie M: The effects of prostaglandin analogues on IOP in prostanoid FP-receptor-deficient mice. Invest Ophthalmol Vis Sci. 2005 Nov;46(11):4159-63. [PubMed:16249494 ]
  2. Nakajima T, Matsugi T, Goto W, Kageyama M, Mori N, Matsumura Y, Hara H: New fluoroprostaglandin F(2alpha) derivatives with prostanoid FP-receptor agonistic activity as potent ocular-hypotensive agents. Biol Pharm Bull. 2003 Dec;26(12):1691-5. [PubMed:14646172 ]
  3. Takagi Y, Nakajima T, Shimazaki A, Kageyama M, Matsugi T, Matsumura Y, Gabelt BT, Kaufman PL, Hara H: Pharmacological characteristics of AFP-168 (tafluprost), a new prostanoid FP receptor agonist, as an ocular hypotensive drug. Exp Eye Res. 2004 Apr;78(4):767-76. [PubMed:15037111 ]
  4. Ocklind A: Effect of latanoprost on the extracellular matrix of the ciliary muscle. A study on cultured cells and tissue sections. Exp Eye Res. 1998 Aug;67(2):179-91. [PubMed:9733584 ]
  5. Maxey KM, Johnson JL, LaBrecque J: The hydrolysis of bimatoprost in corneal tissue generates a potent prostanoid FP receptor agonist. Surv Ophthalmol. 2002 Aug;47 Suppl 1:S34-40. [PubMed:12204699 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

General function:
Involved in transporter activity
Specific function:
Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost
Gene Name:
SLCO2B1
Uniprot ID:
O94956
Molecular weight:
76697.9
References
  1. Kraft ME, Glaeser H, Mandery K, Konig J, Auge D, Fromm MF, Schlotzer-Schrehardt U, Welge-Lussen U, Kruse FE, Zolk O: The prostaglandin transporter OATP2A1 is expressed in human ocular tissues and transports the antiglaucoma prostanoid latanoprost. Invest Ophthalmol Vis Sci. 2010 May;51(5):2504-11. doi: 10.1167/iovs.09-4290. Epub 2009 Dec 17. [PubMed:20019365 ]