NAV

3,20-Pregnanedione

Identification

Generic Name
3,20-Pregnanedione
DrugBank Accession Number
DB07557
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 316.4776
Monoisotopic: 316.240230268
Chemical Formula
C21H32O2
Synonyms
  • 5beta-pregnane-3,20-dione
  • 5β-pregnane-3,20-dione
External IDs
  • NSC-82868
  • U-2411
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNuclear receptor coactivator 1Not AvailableHumans
URetinoic acid receptor RXR-alphaNot AvailableHumans
UNuclear receptor subfamily 1 group I member 3Not AvailableHumans
U3-oxo-5-beta-steroid 4-dehydrogenaseNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 3-oxo-5-beta-steroids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
Substituents
20-oxosteroid / 3-oxo-5-beta-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic ketone / Hydrocarbon derivative / Ketone / Organic oxide / Organic oxygen compound
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 20-oxo steroid, C21-steroid (CHEBI:30154) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030146)
Affected organisms
Not Available

Chemical Identifiers

UNII
105J2Q45A0
CAS number
128-23-4
InChI Key
XMRPGKVKISIQBV-XWOJZHJZSA-N
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/h14,16-19H,4-12H2,1-3H3/t14-,16+,17-,18+,19+,20+,21-/m1/s1
IUPAC Name
(1S,3aS,3bR,5aR,9aS,9bS,11aS)-1-acetyl-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@]2([H])CC(=O)CC[C@]12C

References

General References
Not Available
KEGG Compound
C05479
PubChem Compound
92745
PubChem Substance
99444028
ChemSpider
83723
ChEBI
30154
ChEMBL
CHEMBL486954
ZINC
ZINC000003833953
PDBe Ligand
CI2
PDB Entries
1xv9 / 3cav

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00129 mg/mLALOGPS
logP4.06ALOGPS
logP4.19Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)19.4Chemaxon
pKa (Strongest Basic)-7.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area34.14 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity91.88 m3·mol-1Chemaxon
Polarizability37.77 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9901
Caco-2 permeable+0.7931
P-glycoprotein substrateNon-substrate0.5427
P-glycoprotein inhibitor IInhibitor0.7728
P-glycoprotein inhibitor IIInhibitor0.5666
Renal organic cation transporterNon-inhibitor0.7576
CYP450 2C9 substrateNon-substrate0.8084
CYP450 2D6 substrateNon-substrate0.8784
CYP450 3A4 substrateSubstrate0.6958
CYP450 1A2 substrateNon-inhibitor0.866
CYP450 2C9 inhibitorNon-inhibitor0.8701
CYP450 2D6 inhibitorNon-inhibitor0.9691
CYP450 2C19 inhibitorNon-inhibitor0.8818
CYP450 3A4 inhibitorNon-inhibitor0.8767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9574
Ames testNon AMES toxic0.9348
CarcinogenicityNon-carcinogens0.8708
BiodegradationNot ready biodegradable0.9815
Rat acute toxicity1.9780 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8602
hERG inhibition (predictor II)Non-inhibitor0.6267
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-0kkc-7920000000-b2f5e9cd5c5f21cf2c3e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0093000000-f1d7d253fa8785d59bdc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0009000000-8e264e316e213afcdbea
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014j-0079000000-f4a11fbd755515bec4f7
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0690000000-dc6a3fee299f61d87dc2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0093000000-e20a659b7d70c9e35d65
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-1920000000-415c257e397eb034c0a8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.6126644
predicted
DarkChem Lite v0.1.0
[M-H]-173.958
predicted
DeepCCS 1.0 (2019)
[M+H]+188.2216644
predicted
DarkChem Lite v0.1.0
[M+H]+175.85341
predicted
DeepCCS 1.0 (2019)
[M+Na]+187.6166644
predicted
DarkChem Lite v0.1.0
[M+Na]+181.63145
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nuclear receptor coactivator 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear re...
Gene Name
NCOA1
Uniprot ID
Q15788
Uniprot Name
Nuclear receptor coactivator 1
Molecular Weight
156755.44 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Retinoic acid receptor RXR-alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRA
Uniprot ID
P19793
Uniprot Name
Retinoic acid receptor RXR-alpha
Molecular Weight
50810.835 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details3. Nuclear receptor subfamily 1 group I member 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Binds and transactivates the retinoic acid response elements that control expression of the retinoic acid receptor beta 2 and alcohol dehydrogenase 3 genes. Transactivates both the phenobarbital re...
Gene Name
NR1I3
Uniprot ID
Q14994
Uniprot Name
Nuclear receptor subfamily 1 group I member 3
Molecular Weight
39942.145 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details4. 3-oxo-5-beta-steroid 4-dehydrogenase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid binding
Specific Function
Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihyd...
Gene Name
AKR1D1
Uniprot ID
P51857
Uniprot Name
3-oxo-5-beta-steroid 4-dehydrogenase
Molecular Weight
37376.615 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:23 / Updated at June 12, 2020 16:52