Classification Term: 1405

Oxosteroids (ontology term: CHEMONTID:0001194)

Steroid derivatives carrying a C=O group attached to steroid skeleton." []

found 21 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Steroids and steroid derivatives

Child Taxonomies: 3-oxosteroids, 20-oxosteroids, 11-oxosteroids, 16-oxosteroids, 7-oxosteroids, 6-oxosteroids, 19-oxosteroids, 17-oxosteroids

Mifepristone

(10S,11S,14S,15S,17R)-17-[4-(dimethylamino)phenyl]-14-hydroxy-15-methyl-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-5-one

C29H35NO2 (429.266765)


A progestational and glucocorticoid hormone antagonist. Its inhibition of progesterone induces bleeding during the luteal phase and in early pregnancy by releasing endogenous prostaglandins from the endometrium or decidua. As a glucocorticoid receptor antagonist, the drug has been used to treat hypercortisolism in patients with nonpituitary cushing syndrome. [PubChem] G - Genito urinary system and sex hormones > G03 - Sex hormones and modulators of the genital system > G03X - Other sex hormones and modulators of the genital system > G03XB - Progesterone receptor modulators D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists C147908 - Hormone Therapy Agent > C547 - Hormone Antagonist > C1891 - Progesterone Antagonist D012102 - Reproductive Control Agents > D008600 - Menstruation-Inducing Agents D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents D012102 - Reproductive Control Agents > D000019 - Abortifacient Agents D012102 - Reproductive Control Agents > D008186 - Luteolytic Agents

   

Muzanzagenin

10,15-dihydroxy-5,7,9,13-tetramethyl-5-oxaspiro[oxane-2,6-pentacyclo[10.8.0.0²,⁹.0⁴,⁸.0¹³,¹⁸]icosane]-1(20),17-dien-16-one

C27H38O5 (442.2719098)


Muzanzagenin is found in green vegetables. Muzanzagenin is a constituent of the wild asparagus (Asparagus africanus) Constituent of the wild asparagus (Asparagus africanus). Muzanzagenin is found in green vegetables.

   

Dynorphin A 9-17

(2S)-2-{[(2R)-2-{[(2R)-2-{[(2S)-2-{[(2S)-6-amino-2-{[(2R)-2-{[(2R)-6-amino-2-({[(2S)-1-[(2S)-2-amino-5-carbamimidamidopentanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxyhexylidene]amino}-1-hydroxy-4-methylpentylidene]amino}-1-hydroxyhexylidene]amino}-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino}-3-carboxy-1-hydroxypropylidene]amino}-1-hydroxy-3-(C-hydroxycarbonimidoyl)propylidene]amino}-4-(C-hydroxycarbonimidoyl)butanoate

C53H85N17O14 (1183.646159)


Dynorphin A (9-17) is a fraction of Dynorphin A with only Arg-Pro-Lys-Leu-Lys-Trp-Asp-Asn-Gln peptide chain. Dynorphin A is an endogenous opioid peptide that produces non-opioid receptor-mediated neural excitation.Dynorphin induces calcium influx via voltage-sensitive calcium channels in sensory neurons by activating bradykinin receptors. This action of dynorphin at bradykinin receptors is distinct from the primary signaling pathway activated by bradykinin and underlies the hyperalgesia produced by pharmacological administration of dynorphin by the spinal route in rats and mice. Blockade of spinal B1 or B2 receptor also reverses persistent neuropathic pain but only when there is sustained elevation of endogenous spinal dynorphin, which is required for maintenance of neuropathic pain. These data reveal a mechanism for endogenous dynorphin to promote pain through its agonist action at bradykinin receptors and suggest new avenues for therapeutic intervention. Dynorphin A is a form of dynorphin.Dynorphins are a class of opioid peptides that arise from the precursor protein prodynorphin. When prodynorphin is cleaved during processing by proprotein convertase 2 (PC2), multiple active peptides are released: dynorphin A, dynorphin B, and a/b-neo-endorphin. Depolarization of a neuron containing prodynorphin stimulates PC2 processing, which occurs within synaptic vesicles in the presynaptic terminal. Occasionally, prodynorphin is not fully processed, leading to the release of "big dynorphin."This 32-amino acid molecule consists of both dynorphin A and dynorphin B.Dynorphin A, dynorphin B, and big dynorphin all contain a high proportion of basic amino acid residues, in particular lysine and arginine (29.4\\%, 23.1\\%, and 31.2\\% basic residues, respectively), as well as many hydrophobic residues (41.2\\%, 30.8\\%, and 34.4\\% hydrophobic residues, respectively). Although dynorphins are found widely distributed in the CNS, they have the highest concentrations in the hypothalamus, medulla, pons, midbrain, and spinal cord. Dynorphins are stored in large (80-120 nm diameter) dense-core vesicles that are considerably larger than vesicles storing neurotransmitters. These large dense-core vesicles differ from small synaptic vesicles in that a more intense and prolonged stimulus is needed to cause the large vesicles to release their contents into the synaptic cleft. Dense-core vesicle storage is characteristic of opioid peptides storage. The first clues to the functionality of dynorphins came from Goldstein et al. in their work with opioid peptides. The group discovered an endogenous opioid peptide in the porcine pituitary that proved difficult to isolate. By sequencing the first 13 amino acids of the peptide, they created a synthetic version of the peptide with a similar potency to the natural peptide. Goldstein et al. applied the synthetic peptide to the guinea ileum longitudinal muscle and found it to be an extraordinarily potent opioid peptide. The peptide was called dynorphin (from the Greek dynamis=power) to describe its potency. Dynorphins exert their effects primarily through the κ-opioid receptor (KOR), a G-protein-coupled receptor. Two subtypes of KORs have been identified: K1 and K2. Although KOR is the primary receptor for all dynorphins, the peptides do have some affinity for the μ-opioid receptor (MOR), d-opioid receptor (DOR), N-methyl-D-aspartic acid (NMDA)-type glutamate receptor. Different dynorphins show different receptor selectivities and potencies at receptors. Big dynorphin and dynorphin A have the same selectivity for human KOR, but dynorphin A is more selective for KOR over MOR and DOR than is big dynorphin. Big dynorphin is more potent at KORs than is dynorphin A. Both big dynorphin and dynorphin A are more potent and more selective than dynorphin B (Wikipedia). Dynorphin A (9-17) is a fraction of Dynorphin A with only Arg-Pro-Lys-Leu-Lys-Trp-Asp-Asn-Gln peptide chain

   

Estrone-3,4-quinone

(15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3-diene-5,6,14-trione

C18H20O3 (284.14123700000005)


Estrogen 2,3- and 3,4-quinones are reactive species toward nucleophiles and Michael acceptors. As such, they can bind to DNA and induce cellular damages.Tumors may arise in cells covalently damaged by the free radicals or by the quinones and stimulated to proliferate by hormone receptor-mediated. processes. This hypothesis is supported by the correlation between quinone formation, 8-hydroxylation of guanine bases of DNA and tumor incidence of 4- versus 2-hydroxylated estrogen metabolites. Moreover, estrone-3,4-quinone, but not. estrone-2,3-quinone, induced liver tumors in mice. Estrogen 2,3- and 3,4-quinones are reactive species toward nucleophiles and Michael acceptors. As such, they can bind to DNA and induce cellular damages.Tumors may arise in cells covalently damaged by the free radicals or by the quinones and stimulated to proliferate by hormone receptor-mediated

   

(3beta,17alpha,23S)-17,23-Epoxy-3,29-dihydroxy-27-norlanosta-7,9(11)-diene-15,24-dione

5-hydroxy-6-(hydroxymethyl)-2,3,6,11,15-pentamethyl-5-propanoylspiro[oxolane-2,14-tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecane]-1(17),9-dien-12-one

C29H42O5 (470.30320820000003)


(3beta,17alpha,23S)-17,23-Epoxy-3,29-dihydroxy-27-norlanosta-7,9(11)-diene-15,24-dione is found in herbs and spices. (3beta,17alpha,23S)-17,23-Epoxy-3,29-dihydroxy-27-norlanosta-7,9(11)-diene-15,24-dione is a constituent of Muscari comosum (tassel hyacinth) Constituent of Muscari comosum (tassel hyacinth). (3beta,17alpha,23S)-17,23-Epoxy-3,29-dihydroxy-27-norlanosta-7,9(11)-diene-15,24-dione is found in herbs and spices.

   

17beta-Estradiol-3,4-quinone

(1R,10S,11R,14S,15S)-14-hydroxy-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3-diene-5,6-dione

C18H22O3 (286.15688620000003)


This compound belongs to the family of Ketosteroids. These are steroid derivatives comprising a ketone group attached to steroid skeleton.

   

3-keto Fusidic acid

(2Z)-2-[(3R,4S,5S,8S,9S,10S,11R,13R,14S,16S)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-ylidene]-6-methyl-3-oxohept-5-enoic acid

C31H46O7 (530.3243365999999)


3-keto Fusidic acid is a metabolite of fusidic acid. Fusidic acid is a bacteriostatic antibiotic that is often used topically in creams and eyedrops, but may also be given systemically as tablets or injections. The global problem of advancing antimicrobial resistance has led to a renewed interest in its use recently. (Wikipedia)

   

Maoto

12-methyl-13-oxa-10-azatetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2,4,6,11(15)-tetraen-14-one

C16H17NO2 (255.12592220000002)


   

Aglepristone

17-[4-(dimethylamino)phenyl]-14-hydroxy-15-methyl-14-(prop-1-en-1-yl)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-5-one

C29H37NO2 (431.2824142)


   

(10R,13S,17S)-17-Hydroxy-13-methyl-10-[(4-methylphenyl)methyl]-17-prop-1-ynyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one

(10R,13S,17S)-17-Hydroxy-13-methyl-10-[(4-methylphenyl)methyl]-17-prop-1-ynyl-2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one

C29H34O2 (414.2558664)


   

Dienogest

2-{14-hydroxy-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-14-yl}acetonitrile

C20H25NO2 (311.188519)


   

estradiol alone

5,14-dihydroxy-15-methyl-4-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),5-diene-3-carbaldehyde

C19H24O4 (316.1674504)


   

Lilopristone

17-[4-(dimethylamino)phenyl]-14-hydroxy-14-(3-hydroxyprop-1-en-1-yl)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1,6-dien-5-one

C29H37NO3 (447.27732920000005)


   

N-Demethyl Mifepristone

17-Hydroxy-13-methyl-11-[4-(methylamino)phenyl]-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

C28H33NO2 (415.25111580000004)


   

Norethynodrel

17 alpha-Hydroxy-19-norpregn-5(10)-en-20-yn-3- one mixt. with (17 alpha)-3-methoxy-19-norpregna- 1,3,5(10)-trien-20-yn-17-ol

C20H26O2 (298.1932696)


   

tibolone

14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-2(7)-en-5-one

C21H28O2 (312.2089188)


   

Vilaprisan

17-Hydroxy-13-methyl-11-(4-methylsulfonylphenyl)-17-(1,1,2,2,2-pentafluoroethyl)-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

C27H29F5O4S (544.1706614)


   

(8R,9R,10S,13R,14S)-1,2,3,4,5,6,7,8,9,10,11,12,14,15,16,17-Hexadecahydrocyclopenta[a]phenanthrene-13-carbaldehyde

(8R,9R,10S,13R,14S)-1,2,3,4,5,6,7,8,9,10,11,12,14,15,16,17-Hexadecahydrocyclopenta[a]phenanthrene-13-carbaldehyde

C18H28O (260.2140038)


   

(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one

(8R,9S,13S,14S)-3-Hydroxy-13-methyl-4,6,7,8,9,11,12,14,15,16-decahydro-3H-cyclopenta[a]phenanthren-17-one

C18H24O2 (272.17762039999997)


   

(8S,11R,13R,14S,17S)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

(8S,11R,13R,14S,17S)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-13-methyl-17-prop-1-ynyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one

C29H35NO2 (429.266765)


   

Kuguacin C

(1S,2S,5S,10R,11S,14R,15R)-5-hydroxy-1,6,6,11,15-pentamethyl-14-[(2R)-4-oxopentan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-9-one

C27H42O3 (414.3133782)


Kuguacin c is a member of the class of compounds known as oxosteroids. Oxosteroids are steroid derivatives carrying a C=O group attached to steroid skeleton. Kuguacin c is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Kuguacin c can be found in bitter gourd, which makes kuguacin c a potential biomarker for the consumption of this food product.