Structure Database (LMSD)

HO HO O OH HO
Common Name
15-methyl-15S-PGF2alpha
Systematic Name
9S,11R,15S-trihydroxy-15-methyl-5Z,13E-prostadienoic acid
Synonyms
  • 15-methyl-15S-Prostaglandin F2alpha
  • Carboprost
LM ID
LMFA03010080
Formula
C21H36O5
Exact Mass
Calculate m/z
368.256275
Sum Composition
FA 21:3;O3
Status
Active
Show lipids differing only in stereochemistry/bond geometry

Main

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Prostaglandins [FA0301]

String Representations

InChiKey (Click to copy)
DLJKPYFALUEJCK-IIELGFQLSA-N
InChi (Click to copy)
InChI=1S/C21H36O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-19,22-23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,18+,19-,21+/m1/s1
SMILES (Click to copy)
[C@H]1(/C=C/[C@@](C)(O)CCCCC)[C@H](O)C[C@H](O)[C@@H]1C/C=C\CCCC(=O)O

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
synthetic construct (#32630)
Total synthesis of 15-methylprostaglandins.,
J Am Chem Soc, 1974
Pubmed ID: 4416671

Other Databases

Wikipedia
Carboprost
KEGG ID
C06872
CHEBI ID
3403
LIPIDBANK ID
XPR1762
PubChem CID
5281075
Cayman ID
16743
PDB ID
87Q

Calculated Physicochemical Properties

Heavy Atoms 26
Rings 1
Aromatic Rings 0
Rotatable Bonds 12
Van der Waals Molecular Volume 395.53
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 4.29
Molar Refractivity 104.30

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Created at
-
Updated at
31st Jan 2024