Responsive image

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

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

Responsive image

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
FDBF00047 propionic acid Responsive image CCC(=O)O 0.0395
FDBF00074 but-1-ene Responsive image C(C)C=C 0.0100
FDBF00081 pentane Responsive image CCCCC 0.0316
FDBF00416 butan-1-ol Responsive image C(CC)CO 0.0134
FDBF01747 (2R,4S)-4-hydroxy-2-methyl-cyclopentanone Responsive image O=C1C(CC(C1)O)C 0.0017
FDBF01748 (3R,4S)-3-hydroxy-4-vinyl-cyclopentanone Responsive image O=C1CC(C(C1)O)C=C 0.0017
FDBF01750 (3R,4S)-3-hydroxy-4-[(E)-3-hydroxyprop-1-enyl]cyclopentanone Responsive image O=C1CC(C(C1)O)C=CCO 0.0014
FDBF01758 (3R,4S)-3-hydroxy-4-[(E,3S)-3-hydroxypent-1-enyl]cyclopentanone Responsive image CCC(C=CC1CC(=O)CC1O)O 0.0007
FDBF01759 (2R,3R,4R)-4-hydroxy-3-[(E,3S)-3-hydroxybut-1-enyl]-2-methyl-cyclopentanone Responsive image O=C1C(C(C(C1)O)C=CC(O)C)C 0.0010
FDBF01762 (3S)-hex-1-en-3-ol Responsive image C(C)CC(C=C)O 0.0014
32 , 4