Pregnenolona - Moligand™, ≥98% , CAS No.145-13-1

CAS: 145-13-1 Cat. No.: P129412 Peso molecular: 316.48 Número EC: 205-647-4

GRADE & PURITY Moligand™, ≥98%

Synonyms

3b-Hydroxypregn-5-en-20-one | PREGNENOLONE [WHO-DD] | PREGNENOLONE [INN] | 73R90F7MQ8 | NSC 1616 | Skinostelon | Spectrum5_002057 | 5-Pregnen-3beta-ol-20-one, >=98% | DB02789 | Tox21_112011 | GTPL2376 | HMS3884G16 | Pregnolone | 3beta-Hydroxy-5-pregnene-2

Storage

Conservar a 2-8°C

Shipped In

Hielo húmedo

Descripción general

La pregnenolona es un neuroesteroide endógeno que interviene en la esteroidogénesis de la progesterona, los glucocorticoides, los mineralocorticoides, los andrógenos y los estrógenos, lo que la convierte en una prohormona. Se ha observado que inhibe las corrientes de cloruro activadas por GABA al aumentar la desensibilización del receptor. La pregnenolona es un inhibidor del receptor GABA y un activador del PXR.
Es un neuroesteroide prohormonal también precursor de las hormonas esteroides gonadales y de los corticosteroides suprarrenales.

Specifications

Sinónimos

3b-Hydroxypregn-5-en-20-one | PREGNENOLONE [WHO-DD] | PREGNENOLONE [INN] | 73R90F7MQ8 | NSC 1616 | Skinostelon | Spectrum5_002057 | 5-Pregnen-3beta-ol-20-one, >=98% | DB02789 | Tox21_112011 | GTPL2376 | HMS3884G16 | Pregnolone | 3beta-Hydroxy-5-pregnene-2

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Uno de los pocos "neuroesteroides", es decir, esteroides sintetizados en el cerebro y no en fuentes periféricas. La disminución de los niveles de estos neuroesteroides se ha relacionado con el deterioro cognitivo de los roedores con la edad, pero los estu

Condiciones de almacenamiento de almacenamiento

Conservar a 2-8°C

Enviado en

Hielo húmedo

Grado

Moligand™

Nota

Siempre que sea posible, prepare y utilice las soluciones el mismo día. Sin embargo, si necesita preparar soluciones madre con antelación, le recomendamos que almacene la solución como alícuotas en viales herméticamente cerrados a -20°C. Por lo general, podrán utilizarse durante un mes. Antes de su uso, y antes de abrir el vial, le recomendamos que deje que el producto se equilibre a temperatura ambiente durante al menos 1 hora. ¿Necesita más consejos sobre solubilidad, uso y manipulación? Visite nuestra página de preguntas frecuentes (FAQ) para obtener más información.

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504751770
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504751770
• Sonrisas canónicas: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• IUPAC Name: 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
• InChIKey: ORNBQBCIOKFOEO-QGVNFLHTSA-N
• 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/t15-,16-,17+,18-,19-,20-,21+/m0/s1
• Isómeros SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
• Peso molecular: 316.48
• Reaxy-Rn: 1915502
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1915502&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Steroids and steroid derivatives
      • Subclass Pregnane steroids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Steroids and steroid derivatives
• Subclass: Pregnane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Gluco/mineralocorticoids, progestogins and derivatives
• Alternative Parents: 20-oxosteroids 3-beta-hydroxysteroids 3-beta-hydroxy delta-5-steroids Delta-5-steroids Secondary alcohols Ketones Cyclic alcohols and derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Progestogin-skeleton - 20-oxosteroid - 3-hydroxy-delta-5-steroid - 3-hydroxysteroid - 3-beta-hydroxysteroid - 3-beta-hydroxy-delta-5-steroid - Oxosteroid - Hydroxysteroid - Delta-5-steroid - Cyclic alcohol - Secondary alcohol - Ketone - Organic oxygen compound - Hydrocarbon derivative - Carbonyl group - Alcohol - Organooxygen compound - Organic oxide - Aliphatic homopolycyclic compound
• Descripción: This compound 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.
• External Descriptors: C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Objetivos asociados (humanos)

SHBG Tchem Sex hormone-binding globulin (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

PGR Tclin Progesterone receptor (8562 Activities)

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AR Tclin Androgen Receptor (11781 Activities)

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SULT2A1 Tbio Alcohol sulfotransferase (89 Activities)

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SERPINA6 Tchem Corticosteroid binding globulin (274 Activities)

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UGT1A4 Tbio UDP-glucuronosyltransferase 1A4 (288 Activities)

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A-375 (9258 Activities)

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Daoy (570 Activities)

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HL-60 (67320 Activities)

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HT-29 (80576 Activities)

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MCF7 (126967 Activities)

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MDA-MB-468 (9477 Activities)

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A549 (127892 Activities)

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HCT-116 (91556 Activities)

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WiDr (1835 Activities)

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NCI-H460 (60772 Activities)

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KB (17409 Activities)

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UGT2B7 Tchem UDP-glucuronosyltransferase 2B7 (787 Activities)

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UGT2B17 Tbio UDP-glucuronosyltransferase 2B17 (197 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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G6PD Tchem Glucose-6-phosphate 1-dehydrogenase (778 Activities)

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Skin (286 Activities)

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HSD17B7 Tchem 3-keto-steroid reductase (330 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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SULT2B1 Tbio Sulfotransferase family cytosolic 2B member 1 (4 Activities)

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UGT1A8 Tbio UDP-glucuronosyltransferase 1-8 (233 Activities)

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UGT1A10 Tbio UDP-glucuronosyltransferase 1-10 (257 Activities)

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RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

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Objetivos asociados (no humanos)

ERG11 Cytochrome P450 51 (617 Activities)

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ampC Beta-lactamase AmpC (62480 Activities)

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Nr1i3 Constitutive androstane receptor (427 Activities)

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Shbg Testis-specific androgen-binding protein (10 Activities)

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SULT1E1 Estrogen sulfotransferase (8 Activities)

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Plasmodium falciparum (966862 Activities)

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P388 (20296 Activities)

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PC-12 (7051 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Aorta (2975 Activities)

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SARS-CoV-2 (38078 Activities)

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Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: Soluble in ethanol (22 mg/ml at 25 °C), chloroform, and DMSO (22 mg/ml at 25 °C). Insoluble in water, , , DMSO 22 mg/mL Water Ethanol 22 mg/mL
• Peso molecular: 316.500 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 316.24 Da
• Monoisotopic Mass: 316.24 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 550.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Ruosi Zhang, Mingdong Yao, Haidi Ma, Wenhai Xiao, Ying Wang, Yingjin Yuan.  (2023)  Modular Coculture to Reduce Substrate Competition and Off-Target Intermediates in Androstenedione Biosynthesis.  ACS Synthetic Biology,      [PMID:36857753] [10.1021/acssynbio.2c00590]

2. Xiao-San Li, Mao-Xun Yang, Yu-Hao Luo, He-Hui Zhan, Mei-Fang Chen, Yong-Mei Huang, Li Liu, Xue-Mei Yang.  (2022)  Design, Synthesis and Anticancer Activity of Novel Steroidal Derivatives with D-Ring Fused or Substituted N-Heterocyclic Systems.  CHEMISTRY & BIODIVERSITY,  19  (10): (e202200648).  [PMID:36043381] [10.1002/cbdv.202200648]

3. Yaqin Jia, Zhe Wang, Yuyi Feng, Meixian Wang, Lili Jiang, Zhijun Yu, Xiaoguang Shao, Guiyuan He, Yong Liu.  (2022)  Validity of the association between five steroid hormones quantification and female infertility conditions: A new perspective for clinical diagnosis.  STEROIDS,      [PMID:35803387] [10.1016/j.steroids.2022.109086]

4. Di Xu, Mengyun Wu, Xue Li, Mingyu Xia, Dongchun Liu, Yinghui Dai, Qing Yu, Bin Wu, Dong Wang.  (2018)  Cloning, prokaryotic expression and function of the Bufo bufo gargarizans 3β-hydroxysteroid dehydrogenase (3βHSD) gene.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:30170058] [10.1016/j.ijbiomac.2018.08.165]

5. Jixiu Deng, Pengshuai Zhang, Han Sun, Wang Rongrong, Binbin Wu, Yuemei Li, Beibei Feng, Haowei Sun, Shuoye Yang.  (2025)  Insight into the solid-liquid equilibrium behavior and apparent thermodynamic analysis of polymorphic pregnenolone (Form Ⅰ) in thirteen neat solvents.  THERMOCHIMICA ACTA,      [PMID:] [10.1016/j.tca.2025.179979]