Pregnenolone (BioDeep_00000001411)

 

Secondary id: BioDeep_00000398996, BioDeep_00000861171

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone

化学式: C21H32O2 (316.2402)
中文名称: 孕烯醇酮
谱图信息: 最多检出来源 Homo sapiens(blood) 26%

分子结构信息

SMILES: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
InChI: InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3

描述信息

Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962, 15823613, 16632873, 15134809).
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
COVID info from COVID-19 Disease Map
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Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].
Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

同义名列表

31 个代谢物同义名

1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone; 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethan-1-one; 1-[(1S,2R,5S,10S,11S,14S,15S)-5-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-14-yl]ethanone; (3BETA)-3-HYDROXYPREGN-5-en-20-one; 3β-Hydroxy-5-pregnen-20-one; (3b)-3-hydroxy-Pregn-5-en-20-one; 3β-Hydroxypregn-5-en-20-one; (3Β)-3-hydroxypregn-5-en-20-one; (3b)-3-HYDROXYPREGN-5-en-20-one; 3beta-hydroxypregn-5-en-20-one; 5-Pregnen-3β-ol-20-one; 3Β-hydroxypregn-5-en-20-one; 3b-Hydroxypregn-5-en-20-one; 5-Pregnen-3-beta-ol-20-one; 3-Hydroxypregn-5-en-20-one; 5 Pregnen 3 beta ol 20 one; 5-Pregnen-3beta-ol-20-one; Pregn-5-ene-3b-ol-20-one; Pregn-5-en-3b-ol-20-one; 5-Pregnen-3β-ol-20-one; 5-Pregnen-3b-ol-20-one; Pregnenolone; Skinostelon; Pregnolon; Regnosone; Pregnetan; Pregneton; Prenolon; Natolone; 3β-Hydroxy-5-pregnen-20-one; Pregnenolone



数据库引用编号

26 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(16)

BioCyc(1)

PlantCyc(0)

代谢反应

152 个相关的代谢反应过程信息。

Reactome(141)

BioCyc(5)

WikiPathways(5)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(1)

PathBank(0)

PharmGKB(0)

141 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

亚细胞结构定位 关联基因列表
Cytoplasm 11 ALB, AR, CA1, CLIP1, CNR1, ESR1, GFAP, HSD3B1, MAP2, PEBP1, TUBB4B
Peripheral membrane protein 3 CYP11A1, ESR1, FDXR
Endoplasmic reticulum membrane 3 CYP17A1, HSD3B1, STAR
Mitochondrion membrane 2 CYP11A1, TSPO
Nucleus 7 ALB, AR, CDKL5, CLIP1, ESR1, PEBP1, TUBB4B
cytosol 10 ALB, AR, CA1, CLIP1, ESR1, GFAP, MAP2, PEBP1, TSPO, TUBB4B
dendrite 1 MAP2
mitochondrial membrane 1 TSPO
centrosome 3 ALB, CDKL5, CLIP1
nucleoplasm 3 AR, CDKL5, ESR1
Cell membrane 3 CNR1, ESR1, STAR
Cytoplasmic side 1 ESR1
Cell projection, axon 1 CNR1
Multi-pass membrane protein 3 CNR1, SLC45A2, TSPO
cell cortex 1 CLIP1
dendritic shaft 1 MAP2
glutamatergic synapse 2 CDKL5, CNR1
Golgi apparatus 2 ALB, ESR1
growth cone 1 CNR1
mitochondrial inner membrane 3 CYP11A1, FDXR, HSD3B1
neuronal cell body 2 CYP17A1, MAP2
presynaptic membrane 1 CNR1
Presynapse 1 CNR1
plasma membrane 5 AR, CLIP1, CNR1, ESR1, STAR
Membrane 5 AR, CYP11A1, ESR1, SLC45A2, TSPO
axon 2 CNR1, CYP17A1
extracellular exosome 5 ALB, CA1, PEBP1, TSPO, TUBB4B
endoplasmic reticulum 4 ALB, CYP17A1, HSD3B1, TSPO
extracellular space 2 ALB, IL6
perinuclear region of cytoplasm 1 CDKL5
mitochondrion 5 CYP11A1, FDX1, FDXR, STAR, TSPO
protein-containing complex 3 ALB, AR, ESR1
intracellular membrane-bounded organelle 2 HSD3B1, TSPO
Microsome membrane 1 CYP17A1
Single-pass type I membrane protein 1 STAR
Secreted 2 ALB, IL6
extracellular region 3 ALB, IL6, TUBB4B
Mitochondrion outer membrane 1 CNR1
mitochondrial outer membrane 2 CNR1, TSPO
astrocyte end-foot 1 GFAP
Mitochondrion matrix 1 FDX1
mitochondrial matrix 4 CYP11A1, FDX1, FDXR, STAR
anchoring junction 1 ALB
transcription regulator complex 1 ESR1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDKL5
Extracellular vesicle 1 TUBB4B
actin cytoskeleton 1 CNR1
microtubule cytoskeleton 2 CLIP1, TUBB4B
nucleolus 1 HSD3B1
Melanosome membrane 1 SLC45A2
Mitochondrion inner membrane 2 CYP11A1, FDXR
Membrane raft 1 CNR1
Cytoplasm, cytoskeleton 3 CLIP1, MAP2, TUBB4B
microtubule 3 CLIP1, MAP2, TUBB4B
GABA-ergic synapse 1 CNR1
mitochondrial intermembrane space 2 HSD3B1, STAR
intermediate filament 2 CLIP1, GFAP
ciliary tip 1 CDKL5
nuclear speck 1 AR
dendrite cytoplasm 2 CDKL5, MAP2
Cell projection, ruffle 1 CLIP1
ruffle 1 CLIP1
neuron projection 1 MAP2
ciliary basal body 2 ALB, CDKL5
chromatin 2 AR, ESR1
microtubule associated complex 1 MAP2
cell projection 1 GFAP
mitotic spindle 1 TUBB4B
cytoskeleton 1 TUBB4B
Cytoplasm, cytoskeleton, cilium basal body 1 CDKL5
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
postsynaptic density, intracellular component 1 CDKL5
intercellular bridge 2 HSD3B1, TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
axonemal microtubule 1 TUBB4B
Cytoplasmic vesicle membrane 1 CLIP1
axon initial segment 1 MAP2
Cell projection, dendrite 1 MAP2
euchromatin 1 ESR1
Smooth endoplasmic reticulum membrane 1 HSD3B1
cell body 1 GFAP
dendritic growth cone 2 CDKL5, MAP2
intermediate filament cytoskeleton 1 GFAP
endoplasmic reticulum lumen 2 ALB, IL6
platelet alpha granule lumen 1 ALB
kinetochore 1 CLIP1
proximal neuron projection 1 MAP2
azurophil granule lumen 1 TUBB4B
axon hillock 1 MAP2
[Isoform 1]: Nucleus 1 ESR1
basal dendrite 1 MAP2
cytoplasmic side of lysosomal membrane 1 GFAP
interleukin-6 receptor complex 1 IL6
apical distal dendrite 1 MAP2
dendritic branch 1 MAP2
dendritic filopodium 1 MAP2
distal dendrite 1 MAP2
primary dendrite 1 MAP2
proximal dendrite 1 MAP2
ciliary transition fiber 1 ALB


文献列表

  • Ádám Horváth, Anita Steib, Andrea Nehr-Majoros, Boglárka Kántás, Ágnes Király, Márk Racskó, Balázs István Tóth, Eszter Szánti-Pintér, Eva Kudová, Rita Skoda-Földes, Zsuzsanna Helyes, Éva Szőke. Anti-Nociceptive Effects of Sphingomyelinase and Methyl-Beta-Cyclodextrin in the Icilin-Induced Mouse Pain Model. International journal of molecular sciences. 2024 Apr; 25(9):. doi: 10.3390/ijms25094637. [PMID: 38731855]
  • Fu-Rong Xu, Zhen-Hong Wei, Xiao-Xia Xu, Xiao-Gang Zhang, Chao-Jun Wei, Xiao-Ming Qi, Yong-Hong Li, Xiao-Ling Gao, Yu Wu. The hypothalamic steroidogenic pathway mediates susceptibility to inflammation-evoked depression in female mice. Journal of neuroinflammation. 2023 Dec; 20(1):293. doi: 10.1186/s12974-023-02976-7. [PMID: 38062440]
  • Maritta Kunert, Chloe Langley, Rosalind Lucier, Kerstin Ploss, Carlos E Rodríguez López, Delia A Serna Guerrero, Eva Rothe, Sarah E O'Connor, Prashant D Sonawane. Promiscuous CYP87A enzyme activity initiates cardenolide biosynthesis in plants. Nature plants. 2023 Sep; ?(?):. doi: 10.1038/s41477-023-01515-9. [PMID: 37723202]
  • Yiqin Lin, Yingle Chen, Jingyang Zeng, Shunyuan Li. Nodakenetin Alleviates Inflammatory Pain Hypersensitivity by Suppressing NF-κB Signal Pathway. Neuroimmunomodulation. 2022; 29(4):486-492. doi: 10.1159/000525690. [PMID: 35995035]
  • Alexander Becker, Claudia Götz, Mathias Montenarh, Stephan E Philipp. Control of TRPM3 Ion Channels by Protein Kinase CK2-Mediated Phosphorylation in Pancreatic β-Cells of the Line INS-1. International journal of molecular sciences. 2021 Dec; 22(23):. doi: 10.3390/ijms222313133. [PMID: 34884938]
  • Cecilia Rustichelli, Emanuela Monari, Rossella Avallone, Elisa Bellei, Stefania Bergamini, Aldo Tomasi, Anna Ferrari. Dehydroepiandrosterone sulfate, dehydroepiandrosterone, 5α-dihydroprogesterone and pregnenolone in women with migraine: Analysis of serum levels and correlation with age, migraine years and frequency. Journal of pharmaceutical and biomedical analysis. 2021 Nov; 206(?):114388. doi: 10.1016/j.jpba.2021.114388. [PMID: 34597839]
  • Britton Trabert, Ashley M Geczik, Doug C Bauer, Diana S M Buist, Jane A Cauley, Roni T Falk, Gretchen L Gierach, Trisha F Hue, James V Lacey, Andrea Z LaCroix, Kara A Michels, Jeffrey A Tice, Xia Xu, Louise A Brinton, Cher M Dallal. Association of Endogenous Pregnenolone, Progesterone, and Related Metabolites with Risk of Endometrial and Ovarian Cancers in Postmenopausal Women: The B∼FIT Cohort. Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology. 2021 11; 30(11):2030-2037. doi: 10.1158/1055-9965.epi-21-0669. [PMID: 34465588]
  • K Rehm, A K Hankele, S E Ulbrich, L Bigler. Simultaneous quantification of progestogens in plasma and serum by UHPLC-HRMS employing multiplexed targeted single ion monitoring. Talanta. 2021 Sep; 232(?):122358. doi: 10.1016/j.talanta.2021.122358. [PMID: 34074386]
  • Johanna Ruhnau, Stephanie Hübner, Donna Sunny, Till Ittermann, Michaela F Hartmann, Jan De Lafollie, Stefan A Wudy, Matthias Heckmann. Impact of Gestational and Postmenstrual Age on Excretion of Fetal Zone Steroids in Preterm Infants Determined by Gas Chromatography-Mass Spectrometry. The Journal of clinical endocrinology and metabolism. 2021 08; 106(9):e3725-e3738. doi: 10.1210/clinem/dgab194. [PMID: 33822093]
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  • Kristina M Deligiannidis, Aimee R Kroll-Desrosiers, Yanglan Tan, Michelle L Dubuke, Scott A Shaffer. Longitudinal proneuroactive and neuroactive steroid profiles in medication-free women with, without and at-risk for perinatal depression: A liquid chromatography-tandem mass spectrometry analysis. Psychoneuroendocrinology. 2020 11; 121(?):104827. doi: 10.1016/j.psyneuen.2020.104827. [PMID: 32828068]
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