1,3-CYCLOHEXANEDIOL, 4-METHYLENE-5-[(2E)-[(1S,3AS,7AS)-OCTAHYDRO-1-(5-HYDROXY-5-METHYL-1,3-HEXADIYNYL)-7A-METHYL-4H-INDEN-4-YLIDENE]ETHYLIDENE]-, (1R,3S,5Z)

Identification

Generic Name
1,3-CYCLOHEXANEDIOL, 4-METHYLENE-5-[(2E)-[(1S,3AS,7AS)-OCTAHYDRO-1-(5-HYDROXY-5-METHYL-1,3-HEXADIYNYL)-7A-METHYL-4H-INDEN-4-YLIDENE]ETHYLIDENE]-, (1R,3S,5Z)
DrugBank Accession Number
DB08742
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 394.5464
Monoisotopic: 394.250794954
Chemical Formula
C26H34O3
Synonyms
Not Available

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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Avoid life-threatening adverse drug events & improve clinical decision support.
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNuclear receptor coactivator 1Not AvailableHumans
UVitamin D3 receptorNot 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
Adverseeffects
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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 steroids and steroid derivatives. These are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Not Available
Direct Parent
Steroids and steroid derivatives
Alternative Parents
Ynones / Tertiary alcohols / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homopolycyclic compound / Cyclic alcohol / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Secondary alcohol / Steroid / Tertiary alcohol / Ynone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
CEEUUHVULXTFGS-BQXVGYHGSA-N
InChI
InChI=1S/C26H34O3/c1-18-20(16-22(27)17-24(18)28)11-10-19-8-7-15-26(4)21(12-13-23(19)26)9-5-6-14-25(2,3)29/h10-11,21-24,27-29H,1,7-8,12-13,15-17H2,2-4H3/b19-10+,20-11-/t21-,22+,23-,24-,26+/m0/s1
IUPAC Name
(1R,3S,5Z)-5-{2-[(1S,3aS,4E,7aS)-1-(5-hydroxy-5-methylhexa-1,3-diyn-1-yl)-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexane-1,3-diol
SMILES
C=C1\C(=C/C=C2\CCC[C@]3(C)[C@]([H])(CC[C@@]23[H])C#CC#CC(C)(O)C)C[C@](O)([H])C[C@@]1(O)[H]

References

General References
Not Available
PubChem Compound
11269429
PubChem Substance
99445213
ChemSpider
9444440
ZINC
ZINC000058660808
PDBe Ligand
XE4
PDB Entries
2hbh

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 Solubility0.00898 mg/mLALOGPS
logP4.52ALOGPS
logP3.39ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.06ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity120.55 m3·mol-1ChemAxon
Polarizability47.32 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9812
Blood Brain Barrier+0.7486
Caco-2 permeable+0.7708
P-glycoprotein substrateSubstrate0.7566
P-glycoprotein inhibitor INon-inhibitor0.6002
P-glycoprotein inhibitor IINon-inhibitor0.8568
Renal organic cation transporterNon-inhibitor0.857
CYP450 2C9 substrateNon-substrate0.8186
CYP450 2D6 substrateNon-substrate0.9026
CYP450 3A4 substrateSubstrate0.7574
CYP450 1A2 substrateNon-inhibitor0.7994
CYP450 2C9 inhibitorNon-inhibitor0.7723
CYP450 2D6 inhibitorNon-inhibitor0.9341
CYP450 2C19 inhibitorNon-inhibitor0.6107
CYP450 3A4 inhibitorNon-inhibitor0.6819
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.591
Ames testNon AMES toxic0.9325
CarcinogenicityNon-carcinogens0.8856
BiodegradationNot ready biodegradable0.9962
Rat acute toxicity4.6385 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9182
hERG inhibition (predictor II)Non-inhibitor0.8643
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. Transcription factor that mediates the action of vitamin D3 by controlling the expression of hormone sensitive genes. Recruited to promoters via its interaction with BAZ1B...
Gene Name
VDR
Uniprot ID
P11473
Uniprot Name
Vitamin D3 receptor
Molecular Weight
48288.64 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 21:34 / Updated at June 12, 2020 16:52