
IUPAC name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
Compound class
Therapeutic area
For the termination of pregnancy during the second trimester (from the 12th through the 20th gestational week as calculated from the first day of the last normal menstrual period), as well as for evacuation of the uterine contents in the management of missed abortion or intrauterine fetal death up to 28 weeks of gestational age as calculated from the first day of the last normal menstrual period. Also used in the management of nonmetastatic gestational trophoblastic disease (benign hydatidiform mole). Other indications include improving the cervical inducibility (cervical ;
Common name
Dinoprostone
IUPAC name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
INCHI
InChI=1S/C20H32O5/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/h4,7,12-13,15-17,19,21,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/b7-4-,13-12+/t15-,16+,17+,19+/m0/s1
FORMULA
C20H32O5

Common name
Dinoprostone
IUPAC name
(5Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]hept-5-enoic acid
Molecular weight
352.465
clogP
3.916
clogS
-2.502
HBond Acceptor
5
HBond Donor
3
Total Polar Surface Area
94.83
Number of Rings
1
Rotatable Bond
12
Drug ID | Common name | Structure CAS | SMILE | Frequency |
---|---|---|---|---|
FDBF00004 | acetic acid |
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CC(=O)O | 0.0687 |
FDBF00041 | ethanol |
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CCO | 0.1474 |
FDBF00061 | butyric acid |
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CCCC(=O)O | 0.0131 |
FDBF00077 | (Z)-pent-2-ene |
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C(C)C=CC | 0.0065 |
FDBF00620 | (2S)-but-3-en-2-ol |
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C=CC(O)C | 0.0031 |
FDBF01749 | (2R,3R,4R)-4-hydroxy-2-methyl-3-vinyl-cyclopentanone |
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O=C1C(C(C(C1)O)C=C)C | 0.0017 |
FDBF01764 | (2R,3R,4R)-4-hydroxy-3-[(E,3S)-3-hydroxypent-1-enyl]-2-methyl-cyclopentanone |
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CCC(C=CC1C(C(=O)CC1O)C)O | 0.0007 |
FDBF02037 | (2R,4S)-2-allyl-4-hydroxy-cyclopentanone |
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C(C1C(=O)CC(C1)O)C=C | 0.0003 |
FDBF02039 | (2R,4S)-2-[(Z)-but-2-enyl]-4-hydroxy-cyclopentanone |
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C(C=CC)C1C(=O)CC(C1)O | 0.0003 |
FDBF02041 | (2R,3R,4R)-2-[(Z)-but-2-enyl]-4-hydroxy-3-vinyl-cyclopentanone |
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C(C1C(=O)CC(C1C=C)O)C=CC | 0.0003 |