5α-Pregnane-3,20-dione - ≥97% , CAS No.566-65-4

CAS: 566-65-4 Cat. No.: A304014 Molecular Weight: 316.48 EC Number: 209-297-3

GRADE & PURITY ≥97%

Synonyms

2(1H)-Quinolinone, 7-amino-3,4-dihydro- | 5alpha-pregnane-3,20-dione(allo) | AS-15992 | Pregnane-3,20-dione, (5a)- | 3,20-ALLOPREGNANEDIONE [MI] | MFCD00067132 | HY-W006492 | Pregnane-3,20-dione, 5alpha-allo- | 5f inverted question mark-Pregnane-3,20-dion

Storage

Room temperature,Desiccated

Shipped In

Normal

Specifications

Synonyms

2(1H)-Quinolinone, 7-amino-3, 4-dihydro- | 5alpha-pregnane-3, 20-dione(allo) | AS-15992 | Pregnane-3, 20-dione, (5a)- | 3, 20-ALLOPREGNANEDIONE [MI] | MFCD00067132 | HY-W006492 | Pregnane-3, 20-dione, 5alpha-allo- | 5f inverted question mark-Pregnane-3, 20-dion

Specifications & Purity

≥97%

Storage

Room temperature, Desiccated

Shipped In

Normal

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504756140
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756140
• Canonical Smiles: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(=O)C4)C)C
• IUPAC Name: (5S,8R,9S,10S,13S,14S,17S)-17-acetyl-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• InChIKey: XMRPGKVKISIQBV-BJMCWZGWSA-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/h14,16-19H,4-12H2,1-3H3/t14-,16-,17+,18-,19-,20-,21+/m0/s1
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CCC(=O)C4)C)C
• Molecular Weight: 316.48
• Reaxy-Rn: 2058496
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2058496&ln=

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Steroids and steroid derivatives
• Subclass: Pregnane steroids
• Intermediate Tree Nodes: Not available
• Direct Parent: Gluco/mineralocorticoids, progestogins and derivatives
• Alternative Parents: 20-oxosteroids 3-oxo-5-alpha-steroids Cyclic ketones Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homopolycyclic compounds
• Substituents: Progestogin-skeleton - 20-oxosteroid - 3-oxo-5-alpha-steroid - Oxosteroid - 3-oxosteroid - Cyclic ketone - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homopolycyclic compound
• Description: 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

Associated Targets(Human)

PGR Tclin Progesterone receptor (8562 Activities)

Discover Target: PGR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HEp-2 (3859 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GPBAR1 Tchem G-protein coupled bile acid receptor 1 (1723 Activities)

Discover Target: GPBAR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Nr1i3 Constitutive androstane receptor (427 Activities)

Discover Target: Nr1i3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Specific Rotation[α]: 118° (C=1,CHCl3)
• Melt Point(°C): 204 °C
• Molecular Weight: 316.500 g/mol
• XLogP3: 4.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 316.24 Da
• Monoisotopic Mass: 316.24 Da
• Topological Polar Surface Area: 34.100 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 538.000
• 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

References

1. Wentao An, Hui Lin, Lijuan Ma, Chao Zhang, Yuan Zheng, Qiuxia Cheng, Chuanshun Ma, Xiang Wu, Zihao Zhang, Yani Zhong, Menghui Wang, Dongfang He, Zhao Yang, Lutao Du, Shiqing Feng, Chuanxin Wang, Fan Yang, Peng Xiao, Pengju Zhang, Xiao Yu, Jin-Peng Sun.  (2022)  Progesterone activates GPR126 to promote breast cancer development via the Gi pathway.  PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA,  119  (15): (e2117004119).  [PMID:35394864] [10.1073/pnas.2117004119]