NAV

(9BETA,11ALPHA,13ALPHA,14BETA,17ALPHA)-11-(METHOXYMETHYL)ESTRA-1(10),2,4-TRIENE-3,17-DIOL

Identification

Generic Name
(9BETA,11ALPHA,13ALPHA,14BETA,17ALPHA)-11-(METHOXYMETHYL)ESTRA-1(10),2,4-TRIENE-3,17-DIOL
DrugBank Accession Number
DB07707
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 316.4345
Monoisotopic: 316.203844762
Chemical Formula
C20H28O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UEstrogen receptor alphaNot AvailableHumans
UNuclear receptor coactivator 2Not 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 estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-hydroxysteroids / 17-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Cyclic alcohols and derivatives / Dialkyl ethers / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 17-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aromatic homopolycyclic compound / Benzenoid / Cyclic alcohol / Dialkyl ether / Estrogen-skeleton / Ether
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LEOPSILMAOYZBO-IUTAEKPZSA-N
InChI
InChI=1S/C20H28O3/c1-20-10-13(11-23-2)19-15-6-4-14(21)9-12(15)3-5-16(19)17(20)7-8-18(20)22/h4,6,9,13,16-19,21-22H,3,5,7-8,10-11H2,1-2H3/t13-,16+,17+,18+,19-,20+/m1/s1
IUPAC Name
(1S,3aS,3bS,9bR,10S,11aS)-10-(methoxymethyl)-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthrene-1,7-diol
SMILES
[H][C@]1(O)CC[C@@]2([H])[C@]3([H])CCC4=CC(O)=CC=C4[C@@]3([H])[C@@]([H])(COC)C[C@]12C

References

General References
Not Available
PubChem Compound
23728517
PubChem Substance
99444178
ChemSpider
21169213
ZINC
ZINC000013610524
PDBe Ligand
EED
PDB Entries
2qgt

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 Solubility0.00706 mg/mLALOGPS
logP3.18ALOGPS
logP3.32Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)10.31Chemaxon
pKa (Strongest Basic)-0.89Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.69 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity91.06 m3·mol-1Chemaxon
Polarizability36.6 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9966
Blood Brain Barrier+0.92
Caco-2 permeable+0.8218
P-glycoprotein substrateSubstrate0.8322
P-glycoprotein inhibitor INon-inhibitor0.7205
P-glycoprotein inhibitor IINon-inhibitor0.521
Renal organic cation transporterNon-inhibitor0.7026
CYP450 2C9 substrateNon-substrate0.7949
CYP450 2D6 substrateNon-substrate0.7395
CYP450 3A4 substrateSubstrate0.7611
CYP450 1A2 substrateInhibitor0.7188
CYP450 2C9 inhibitorNon-inhibitor0.7845
CYP450 2D6 inhibitorNon-inhibitor0.9274
CYP450 2C19 inhibitorNon-inhibitor0.767
CYP450 3A4 inhibitorNon-inhibitor0.6627
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7979
Ames testNon AMES toxic0.8617
CarcinogenicityNon-carcinogens0.9188
BiodegradationNot ready biodegradable0.982
Rat acute toxicity2.0746 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.857
hERG inhibition (predictor II)Inhibitor0.7341
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/MSsplash10-014i-0089000000-38dfb8aee6290307c044
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0029000000-759d515f9995298ac920
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ab9-1190000000-8fc2a638898bbb8ddb5f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-0094000000-da99f114c362f24c5c29
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01b9-0091000000-22a2c341ae6e4b2033a9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00l2-2940000000-da7ab51d268fc25d51c0
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]-182.22342
predicted
DeepCCS 1.0 (2019)
[M+H]+184.11884
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.89676
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Estrogen receptor alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 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. Nuclear receptor coactivator 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription coactivator activity
Specific Function
Transcriptional coactivator for steroid receptors and nuclear receptors. Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1). Required with NCOA1 to ...
Gene Name
NCOA2
Uniprot ID
Q15596
Uniprot Name
Nuclear receptor coactivator 2
Molecular Weight
159155.645 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 21:25 / Updated at June 12, 2020 16:52