| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:29:32 UTC |
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| Update Date | 2020-06-04 23:02:00 UTC |
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| BMDB ID | BMDB0000374 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 17-Hydroxyprogesterone |
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| Description | 17-17-17-hydroxyprogesterone, also known as 17-hydroxyprogesterone or 17-17-hydroxyprogesterone, 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. Thus, 17-17-hydroxyprogesterone is considered to be a steroid lipid molecule. 17-17-17-hydroxyprogesterone exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. 17-17-17-hydroxyprogesterone exists in all living organisms, ranging from bacteria to humans. 17-17-17-hydroxyprogesterone participates in a number of enzymatic reactions, within cattle. In particular, 17-17-17-hydroxyprogesterone can be converted into 21-deoxycortisol through the action of the enzyme cytochrome P450 11B1. In addition, 17-17-17-hydroxyprogesterone can be biosynthesized from progesterone through its interaction with the enzyme steroid 17-alpha-hydroxylase/17,20 lyase. In cattle, 17-17-hydroxyprogesterone is involved in the metabolic pathway called the steroidogenesis pathway. 17-17-17-hydroxyprogesterone is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 17-Hydroxypregn-4-en-3,20-dione | ChEBI | | 17alpha-Hydroxy-4-pregnene-3,20-dione | ChEBI | | 17alpha-Hydroxy-progesterone | ChEBI | | delta(4)-Pregnene-17alpha-ol-3,20-dione | ChEBI | | Hidroxiprogesterona | ChEBI | | Hydroxyprogesterone | ChEBI | | Hydroxyprogesteronum | ChEBI | | Pregn-4-ene-3,20-dione-17-ol | ChEBI | | 17a-Hydroxy-4-pregnene-3,20-dione | Generator | | 17Α-hydroxy-4-pregnene-3,20-dione | Generator | | 17a-Hydroxy-progesterone | Generator | | 17Α-hydroxy-progesterone | Generator | | delta(4)-Pregnene-17a-ol-3,20-dione | Generator | | Δ(4)-pregnene-17α-ol-3,20-dione | Generator | | Δ(4)-pregnene-17a-ol-3,20-dione | HMDB | | 17-alpha-Hydroxyprogesterone | HMDB | | 17-Hydroxypregn-4-ene-3,20-dione | HMDB | | 17-OH Progesterone | HMDB | | 17-OHP | HMDB | | 17a-Hydroxypregn-4-ene-3,20-dione | HMDB | | 17a-Hydroxyprogesterone | HMDB | | 17alpha-Hydroxyprogesterone | HMDB | | D4-Pregnen-17a-ol-3,20-dione | HMDB | | Gestageno | HMDB | | Gestageno gador | HMDB | | Pregn-4-en-17a-ol-3,20-dione | HMDB | | Prodix | HMDB | | Prodox | HMDB | | 17 Hydroxyprogesterone | HMDB | | 17-Hydroxyprogesterone, (17 alpha)-isomer | HMDB | | 17 alpha Hydroxyprogesterone | HMDB | | 17 alpha-Hydroxyprogesterone | HMDB | | 17-Hydroxyprogesterone, (9 beta, 10 alpha)-isomer | HMDB |
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| Chemical Formula | C21H30O3 |
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| Average Molecular Weight | 330.4611 |
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| Monoisotopic Molecular Weight | 330.219494826 |
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| IUPAC Name | (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 |
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| Traditional Name | (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 |
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| CAS Registry Number | 68-96-2 |
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| 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 |
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| InChI Identifier | 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 |
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| InChI Key | DBPWSSGDRRHUNT-CEGNMAFCSA-N |
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| Chemical Taxonomy |
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| Description | 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. |
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| Kingdom | Organic compounds |
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| Super Class | Lipids and lipid-like molecules |
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| Class | Steroids and steroid derivatives |
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| Sub Class | Pregnane steroids |
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| Direct Parent | Gluco/mineralocorticoids, progestogins and derivatives |
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| Alternative Parents | |
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| Substituents | - Progestogin-skeleton
- 20-oxosteroid
- 3-oxo-delta-4-steroid
- 3-oxosteroid
- 17-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Delta-4-steroid
- Cyclohexenone
- Alpha-hydroxy ketone
- Cyclic alcohol
- Tertiary alcohol
- Cyclic ketone
- Ketone
- Organic oxygen compound
- Carbonyl group
- Hydrocarbon derivative
- Alcohol
- Organooxygen compound
- Organic oxide
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic compounds |
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| External Descriptors | - 17alpha-hydroxy steroid (CHEBI:17252 )
- Progestagens (C01176 )
- C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030161 )
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| Ontology |
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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | - Cell membrane
- Cytoplasm
- Endoplasmic reticulum
- Membrane
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 219 - 220 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.00648 mg/mL | Not Available | | LogP | 3.17 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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