4-[(1S,2S,5S)-5-(HYDROXYMETHYL)-6,8,9-TRIMETHYL-3-OXABICYCLO[3.3.1]NON-7-EN-2-YL]PHENOL

Identification

Generic Name
4-[(1S,2S,5S)-5-(HYDROXYMETHYL)-6,8,9-TRIMETHYL-3-OXABICYCLO[3.3.1]NON-7-EN-2-YL]PHENOL
DrugBank Accession Number
DB07195
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 288.3814
Monoisotopic: 288.172544634
Chemical Formula
C18H24O3
Synonyms
Not Available

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 1-hydroxy-2-unsubstituted benzenoids. These are phenols that a unsubstituted at the 2-position.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenols
Sub Class
1-hydroxy-2-unsubstituted benzenoids
Direct Parent
1-hydroxy-2-unsubstituted benzenoids
Alternative Parents
Oxanes / Benzene and substituted derivatives / Oxacyclic compounds / Dialkyl ethers / Primary alcohols / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alcohol / Aromatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Monocyclic benzene moiety / Organic oxygen compound / Organoheterocyclic compound / Organooxygen compound
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DTZWKYVREFMAJA-QXWBOSQLSA-N
InChI
InChI=1S/C18H24O3/c1-11-8-12(2)18(9-19)10-21-17(16(11)13(18)3)14-4-6-15(20)7-5-14/h4-8,12-13,16-17,19-20H,9-10H2,1-3H3/t12-,13-,16+,17+,18-/m0/s1
IUPAC Name
4-[(1S,2S,5S,6S,9S)-5-(hydroxymethyl)-6,8,9-trimethyl-3-oxabicyclo[3.3.1]non-7-en-2-yl]phenol
SMILES
[H][C@]1(C)C=C(C)[C@]2([H])[C@]([H])(C)[C@@]1(CO)CO[C@]2([H])C1=CC=C(O)C=C1

References

General References
Not Available
PubChem Compound
6857699
PubChem Substance
99443666
ChemSpider
5257033
ZINC
ZINC000038190856
PDBe Ligand
689
PDB Entries
1zky

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 Solubility0.0503 mg/mLALOGPS
logP2.52ALOGPS
logP2.72Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)9.47Chemaxon
pKa (Strongest Basic)-2.8Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.69 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity83.83 m3·mol-1Chemaxon
Polarizability32.23 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.5451
Caco-2 permeable+0.6393
P-glycoprotein substrateSubstrate0.7722
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IIInhibitor0.5484
Renal organic cation transporterNon-inhibitor0.8145
CYP450 2C9 substrateNon-substrate0.8157
CYP450 2D6 substrateNon-substrate0.8457
CYP450 3A4 substrateSubstrate0.5201
CYP450 1A2 substrateInhibitor0.6532
CYP450 2C9 inhibitorNon-inhibitor0.537
CYP450 2D6 inhibitorNon-inhibitor0.9313
CYP450 2C19 inhibitorInhibitor0.771
CYP450 3A4 inhibitorNon-inhibitor0.8128
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.799
Ames testNon AMES toxic0.5555
CarcinogenicityNon-carcinogens0.8555
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.9882 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8749
hERG inhibition (predictor II)Non-inhibitor0.8132
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/MSsplash10-0079-0090000000-3469b45bef8e87020bcd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-de3c3573fce48df35736
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-05to-1390000000-221e06b36bd51f7f8bf1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-0090000000-5873c818957de9d1f1a9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004m-4390000000-3f5a875ef9c7efae01ee
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0930000000-e85530d928d62e91ab9d
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]-172.321
predicted
DeepCCS 1.0 (2019)
[M+H]+174.71657
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.6291
predicted
DeepCCS 1.0 (2019)

Targets

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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]
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 21:19 / Updated at June 12, 2020 16:52