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Eicosanoids

Description:

Unsaturated C20 fatty acids or skeletally related compounds. These include prostaglandins, thromboxanes, leukotrienes and other oxygenated derivatives, which are produced primarily by three classes of enzymes, cyclooxygenases (COX-1 and COX-2), lipoxygenases (LOX) and cytochrome P450 mono-oxygenases.

Ancestors:

Organic compounds ⮕ Lipids and lipid-like molecules ⮕ Fatty Acyls ⮕ Eicosanoids

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  1. Misoprostol
    Misoprostol
    CAS: 59122-46-2 EC Number: 664-288-5 Formula: C22H38O5 Molecular Weight: 382.53
    ≥98%
    Out of Stock Item #: M1505555
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    Technical Identifiers
    IUPAC Name
    methyl 7-[(1R,2R,3R)-3-hydroxy-2-[(E)-4-hydroxy-4-methyloct-1-enyl]-5-oxocyclopentyl]heptanoate
    SMILES
    CCCCC(C)(CC=CC1C(CC(=O)C1CCCCCCC(=O)OC)O)O
    InChIKey
    OJLOPKGSLYJEMD-URPKTTJQSA-N
    InChI
    1S/C22H38O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h10,12,17-18,20,24,26H,4-9,11,13-16H2,1-3H3/b12-10+/t17-,18-,2show more
  2. iloprost r-isomer
    iloprost r-isomer
    CAS: 74843-13-3 PubChem CID: 51397006 Formula: C22H32O4 Molecular Weight: 360.49
    Out of Stock Item #: I1017566
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (5E)-5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(E,3S,4R)-3-hydroxy-4-methyloct-1-en-6-ynyl]-3,3a,4,5,6,6a-hexahydro-1H-pentalen-2-ylidene]pentanoic acid
    SMILES
    CC#CCC(C)C(C=CC1C(CC2C1CC(=CCCCC(=O)O)C2)O)O
    InChIKey
    HIFJCPQKFCZDDL-GBSCXWAGSA-N
    InChI
    1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+show more
  3. Isopropyl Cloprostenate
    Isopropyl Cloprostenate
    CAS: 157283-66-4 PubChem CID: 59938277 Formula: C25H35ClO6 Molecular Weight: 466.99
    Out of Stock Item #: I1034630
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    propan-2-yl (Z)-7-[(1R,2R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
    SMILES
    CC(C)OC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC(=CC=C2)Cl)O)O)O
    InChIKey
    OCNSAYQJDKJOLH-AHTXBMBWSA-N
    InChI
    1S/C25H35ClO6/c1-17(2)32-25(30)11-6-4-3-5-10-21-22(24(29)15-23(21)28)13-12-19(27)16-31-20-9-7-8-18(26)14-20/h3,5,7-9,12-14,17,19,21-24,27-29H,4,6,10-1show more
  4. 9(R)-Hete
    9(R)-Hete
    CAS: 107656-14-4 PubChem CID: 5283166
    Out of Stock Item #: R988528
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (5Z,7E,9R,11Z,14Z)-9-hydroxyicosa-5,7,11,14-tetraenoic acid
    SMILES
    CCCCCC=CCC=CCC(C=CC=CCCCC(=O)O)O
    InChIKey
    KATOYYZUTNAWSA-AZFZJQGOSA-N
    InChI
    1S/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9-,13-10show more
  5. (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxo-5-phenylpent-1-enyl)cyclopentyl)hept-5-enoic acid
    (Z)-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxo-5-phenylpent-1-enyl)cyclopentyl)hept-5-enoic acid
    CAS: 949564-89-0 Formula: C23H30O5 Molecular Weight: 386.5
    Out of Stock Item #: Z1238946
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxo-5-phenylpent-1-enyl]cyclopentyl]hept-5-enoic acid
    SMILES
    C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/C(=O)CCC2=CC=CC=C2)C/C=C\CCCC(=O)O)O
    InChIKey
    HHEYLKRDELKWGI-RKJYIPPQSA-N
    InChI
    1S/C23H30O5/c24-18(13-12-17-8-4-3-5-9-17)14-15-20-19(21(25)16-22(20)26)10-6-1-2-7-11-23(27)28/h1,3-6,8-9,14-15,19-22,25-26H,2,7,10-13,16H2,(H,27,28)/bshow more
  6. (E)-N-ethyl-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)cyclopentyl)hept-5-enamide
    (E)-N-ethyl-7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((S,E)-3-hydroxy-5-phenylpent-1-en-1-yl)cyclopentyl)hept-5-enamide
    CAS: 1163135-95-2 PubChem CID: 6505201 Formula: C25H37NO4 Molecular Weight: 415.57
    Out of Stock Item #: E1041581
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]-N-ethylhept-5-enamide
    SMILES
    CCNC(=O)CCCC=CCC1C(CC(C1C=CC(CCC2=CC=CC=C2)O)O)O
    InChIKey
    AQOKCDNYWBIDND-ABRBVVEGSA-N
    InChI
    1S/C25H37NO4/c1-2-26-25(30)13-9-4-3-8-12-21-22(24(29)18-23(21)28)17-16-20(27)15-14-19-10-6-5-7-11-19/h3,5-8,10-11,16-17,20-24,27-29H,2,4,9,12-15,18H2,show more
  7. 12-Hydroxyeicosapentaenoic acid, (12R)-
    12-Hydroxyeicosapentaenoic acid, (12R)-
    CAS: 109430-12-8 Formula: C20H30O3 Molecular Weight: 318.400
    Out of Stock Item #: H1012026
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (5Z,8Z,10E,12R,14Z,17Z)-12-hydroxyicosa-5,8,10,14,17-pentaenoic acid
    SMILES
    CC/C=C\C/C=C\C[C@H](/C=C/C=C\C/C=C\CCCC(=O)O)O
    InChIKey
    MCRJLMXYVFDXLS-IHWYZUJNSA-N
    InChI
    1S/C20H30O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h3-4,7-11,13-14,17,19,21H,2,5-6,12,15-16,18H2,1H3,(H,22,23)/b4-3-,9-7-,11-8-,show more
  8. 11R-Hede
    11R-Hede
    CAS: 330800-88-9 Formula: C20H36O3 Molecular Weight: 324.500
    Out of Stock Item #: R946609
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (11R,12E,14Z)-11-hydroxyicosa-12,14-dienoic acid
    SMILES
    CCCCC/C=C\C=C\[C@@H](CCCCCCCCCC(=O)O)O
    InChIKey
    HDMIRVFIVOGVIC-VOYJXKAKSA-N
    InChI
    1S/C20H36O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h7,10,13,16,19,21H,2-6,8-9,11-12,14-15,17-18H2,1H3,(H,22,23)/b10-7-,16-13+/t1show more
  9. 19(S)-Hete
    19(S)-Hete
    CAS: 115461-40-0 Formula: C20H32O3 Molecular Weight: 320.500
    Out of Stock Item #: S1007556
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (5Z,8Z,11Z,14Z,19S)-19-hydroxyicosa-5,8,11,14-tetraenoic acid
    SMILES
    C[C@@H](CCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O)O
    InChIKey
    XFUXZHQUWPFWPR-DZBJBCEBSA-N
    InChI
    1S/C20H32O3/c1-19(21)17-15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18-20(22)23/h3-6,9-12,19,21H,2,7-8,13-18H2,1H3,(H,22,23)/b5-3-,6-4-,11-9-,12-10-/t19-/m0/show more
  10. Tafluprost ethyl ester
    Tafluprost ethyl ester
    CAS: 209860-89-9 PubChem CID: 12115238
    Out of Stock Item #: T941684
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    ethyl (Z)-7-[(1R,2R,3R,5S)-2-[(E)-3,3-difluoro-4-phenoxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
    SMILES
    CCOC(=O)CCCC=CCC1C(CC(C1C=CC(COC2=CC=CC=C2)(F)F)O)O
    InChIKey
    SPWJIEVPQKMQPO-MSHHKXPZSA-N
    InChI
    1S/C24H32F2O5/c1-2-30-23(29)13-9-4-3-8-12-19-20(22(28)16-21(19)27)14-15-24(25,26)17-31-18-10-6-5-7-11-18/h3,5-8,10-11,14-15,19-22,27-28H,2,4,9,12-13,1show more
  11. Prostaglandin K2
    Prostaglandin K2
    CAS: 275816-51-8 Formula: C20H30O5 Molecular Weight: 350.400
    Out of Stock Item #: P970064
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (Z)-7-[(1R,2R)-2-[(E,3S)-3-hydroxyoct-1-enyl]-3,5-dioxocyclopentyl]hept-5-enoic acid
    SMILES
    CCCCC[C@@H](/C=C/[C@@H]1[C@H](C(=O)CC1=O)C/C=C\CCCC(=O)O)O
    InChIKey
    LGMXPVXJSFPPTQ-DJUJBXLVSA-N
    InChI
    1S/C20H30O5/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/h4,7,12-13,15-17,21H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t1show more
  12. N-Cyclopropyl Methyl Bimatoprost
    N-Cyclopropyl Methyl Bimatoprost
    CAS: 1138395-10-4 PubChem CID: 25270601 Formula: C27H39NO4 Molecular Weight: 441.6
    Out of Stock Item #: N942886
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    Pricing & Pack Sizes
    Technical Identifiers
    IUPAC Name
    (Z)-N-(cyclopropylmethyl)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]cyclopentyl]hept-5-enamide
    SMILES
    C1CC1CNC(=O)CCCC=CCC2C(CC(C2C=CC(CCC3=CC=CC=C3)O)O)O
    InChIKey
    IBUQJJFOXZIFFM-SKHQJWOMSA-N
    InChI
    1S/C27H39NO4/c29-22(15-14-20-8-4-3-5-9-20)16-17-24-23(25(30)18-26(24)31)10-6-1-2-7-11-27(32)28-19-21-12-13-21/h1,3-6,8-9,16-17,21-26,29-31H,2,7,10-15,show more
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