1.0 2011-09-21 00:06:39 UTC 2015-10-09 22:28:53 UTC FDB021992 17-Hydroxyprogesterone It serves as an intermediate in the biosynthesis of hydrocortisone and gonadal steroid hormones. It is derived from progesterone via 17-hydroxylase, a P450c17 enzyme, or from 17-hydroxypregnenolone via 3β-hydroxysteroid dehydrogenase/Δ5-4 isomerase. 17-Hydroxyprogesterone is a natural progestin and in pregnancy increases in the third trimester primarily due to fetal adrenal production. This hormone is primarily produced in the adrenal glands and to some degree in the gonads, specifically the corpus luteum of the ovary. Normal levels are 3-90 ng/dl in children, and in women, 15-70 ng/dl prior to ovulation, and 35-290 ng/dl during the luteal phase. Measurements of levels of 17-hydroxyprogesterone are useful in the evaluation of patients with suspected congenital adrenal hyperplasia as the typical enzymes that are defective, namely 21-hydroxylase and 11β-hydroxylase, lead to a build-up of 17OHP. In contrast, the rare patient with 17α-hydroxylase deficiency will have very low or undetectable levels of 17OHP. 17OHP levels can also be used to measure contribution of progestational activity of the corpus luteum during pregnancy as progesterone but not 17OHP is also contributed by the placenta. [HMDB] 17-alpha-hydroxyprogesterone 17-Hydroxypregn-4-en-3,20-dione 17-Hydroxypregn-4-ene-3,20-dione 17-Hydroxyprogesterone 17-OH Progesterone 17-OHP 17a-Hydroxy-4-pregnene-3,20-dione 17a-Hydroxy-progesterone 17a-Hydroxypregn-4-ene-3,20-dione 17a-Hydroxyprogesterone 17alpha-Hydroxy-4-pregnene-3,20-dione 17alpha-Hydroxy-progesterone 17alpha-hydroxyprogesterone 17α-hydroxy-4-pregnene-3,20-dione 17α-hydroxy-progesterone 17α-hydroxyprogesterone D4-Pregnen-17a-ol-3,20-dione delta(4)-Pregnene-17a-ol-3,20-dione delta(4)-Pregnene-17alpha-ol-3,20-dione Gestageno Gestageno Gador Hidroxiprogesterona Hydroxyprogesterone Hydroxyprogesteronum Pregn-4-en-17a-ol-3,20-dione Pregn-4-ene-3,20-dione-17-ol Prodix Prodox δ(4)-pregnene-17a-ol-3,20-dione δ(4)-pregnene-17α-ol-3,20-dione C21H30O3 330.4611 330.219494826 (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one 68-96-2 [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 DBPWSSGDRRHUNT-CEGNMAFCSA-N belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety. Gluco/mineralocorticoids, progestogins and derivatives Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Pregnane steroids Aliphatic homopolycyclic compounds 17-hydroxysteroids 20-oxosteroids 3-oxo delta-4-steroids Alpha-hydroxy ketones Cyclic alcohols and derivatives Cyclohexenones Delta-4-steroids Hydrocarbon derivatives Organic oxides Tertiary alcohols 17-hydroxysteroid 20-oxosteroid 3-oxo-delta-4-steroid 3-oxosteroid Alcohol Aliphatic homopolycyclic compound Alpha-hydroxy ketone Carbonyl group Cyclic alcohol Cyclic ketone Cyclohexenone Delta-4-steroid Hydrocarbon derivative Hydroxysteroid Ketone Organic oxide Organic oxygen compound Organooxygen compound Oxosteroid Progestogin-skeleton Tertiary alcohol 17alpha-hydroxy steroid C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives Progestagens Solid logp 2.99 ALOGPS logs -4.05 ALOGPS solubility 2.93e-02 g/l ALOGPS logp 3.4 ChemAxon pka_strongest_acidic 12.7 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac (1S,2R,10R,11S,14R,15S)-14-acetyl-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one ChemAxon average_mass 330.4611 ChemAxon mono_mass 330.219494826 ChemAxon smiles [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C ChemAxon formula C21H30O3 ChemAxon inchi InChI=1S/C21H30O3/c1-13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 ChemAxon inchikey DBPWSSGDRRHUNT-CEGNMAFCSA-N ChemAxon polar_surface_area 54.37 ChemAxon refractivity 94.11 ChemAxon polarizability 37.9 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Androgen and Estrogen Metabolism SMP00068 map00150 Steroidogenesis SMP00130 map00140 Specdb::EiMs 1116 Specdb::NmrOneD 1349 Specdb::MsMs 588 Specdb::MsMs 589 Specdb::MsMs 590 Specdb::MsMs 4046 Specdb::MsMs 302602 Specdb::MsMs 302603 Specdb::MsMs 302604 Specdb::MsMs 345370 Specdb::MsMs 345371 Specdb::MsMs 345372 Specdb::MsMs 451602 Specdb::MsMs 2244420 Specdb::MsMs 2245673 Specdb::MsMs 2246520 Specdb::MsMs 2247775 Specdb::MsMs 2248620 Specdb::MsMs 2249748 Specdb::MsMs 2317373 Specdb::MsMs 2317374 Specdb::MsMs 2317375 Specdb::MsMs 2617583 Specdb::MsMs 2617584 Specdb::MsMs 2617585 Specdb::NmrTwoD 1291 Specdb::CMs 2225 Specdb::CMs 16572 Specdb::CMs 27999 Specdb::CMs 31136 Specdb::CMs 37476 Specdb::CMs 133582 Specdb::CMs 141316 Specdb::CMs 1059859 Specdb::CMs 1059860 Specdb::CMs 1059863 Specdb::CMs 1059865 Specdb::CMs 1059867 HMDB00374 3QZ #<Reference:0x000055ce324c2970> #<Reference:0x000055ce324c27b8> #<Reference:0x000055ce324c2600> #<Reference:0x000055ce324c2448> #<Reference:0x000055ce324c2290> #<Reference:0x000055ce324c20d8> #<Reference:0x000055ce324c1f20> #<Reference:0x000055ce324c1d68> #<Reference:0x000055ce324c1bb0> #<Reference:0x000055ce324c19f8> #<Reference:0x000055ce324c1840> #<Reference:0x000055ce324c1688> #<Reference:0x000055ce324c14d0> #<Reference:0x000055ce324c1318> #<Reference:0x000055ce324c1160> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Cytochrome P450, family 21, subfamily A, polypeptide 2 Q08AG9 CYP21A2