NAV

6-(2,3,4,5,6,7-HEXAHYDRO-2,4,4-TRIMETHYL-1-METYLENEINDEN-2-YL)-3-METHYLHEXA-2,4-DIENOIC ACID

Identification

Generic Name
6-(2,3,4,5,6,7-HEXAHYDRO-2,4,4-TRIMETHYL-1-METYLENEINDEN-2-YL)-3-METHYLHEXA-2,4-DIENOIC ACID
DrugBank Accession Number
DB08467
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 300.4351
Monoisotopic: 300.20893014
Chemical Formula
C20H28O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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 bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Bicyclic monoterpenoids
Alternative Parents
Medium-chain fatty acids / Methyl-branched fatty acids / Unsaturated fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic homopolycyclic compound / Bicyclic monoterpenoid / Branched fatty acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Fatty acid / Fatty acyl / Hydrocarbon derivative / Medium-chain fatty acid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
HEVXQLBAMFMFKU-IAZPEVBMSA-N
InChI
InChI=1S/C20H28O2/c1-14(12-18(21)22)8-6-11-20(5)13-17-16(15(20)2)9-7-10-19(17,3)4/h6,8,12H,2,7,9-11,13H2,1,3-5H3,(H,21,22)/b8-6+,14-12+/t20-/m1/s1
IUPAC Name
(2E,4E)-3-methyl-6-[(2R)-2,4,4-trimethyl-1-methylidene-2,3,4,5,6,7-hexahydro-1H-inden-2-yl]hexa-2,4-dienoic acid
SMILES
O=C(O)\C=C(/C)\C=C\C[C@]1(C)CC2=C(CCCC2(C)C)C1=C

References

General References
Not Available
PubChem Compound
5289278
PubChem Substance
99444938
ChemSpider
4451273
ZINC
ZINC000015475858
PDBe Ligand
RE9
PDB Entries
1cbq

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 Solubility0.00892 mg/mLALOGPS
logP5.75ALOGPS
logP4.67Chemaxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.54Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity93.62 m3·mol-1Chemaxon
Polarizability34.61 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9937
Blood Brain Barrier+0.9742
Caco-2 permeable+0.7317
P-glycoprotein substrateNon-substrate0.5236
P-glycoprotein inhibitor INon-inhibitor0.7341
P-glycoprotein inhibitor IIInhibitor0.6366
Renal organic cation transporterNon-inhibitor0.8369
CYP450 2C9 substrateNon-substrate0.8687
CYP450 2D6 substrateNon-substrate0.8959
CYP450 3A4 substrateSubstrate0.656
CYP450 1A2 substrateNon-inhibitor0.7741
CYP450 2C9 inhibitorNon-inhibitor0.7324
CYP450 2D6 inhibitorNon-inhibitor0.9371
CYP450 2C19 inhibitorNon-inhibitor0.7409
CYP450 3A4 inhibitorNon-inhibitor0.8779
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8452
Ames testNon AMES toxic0.8667
CarcinogenicityNon-carcinogens0.8357
BiodegradationNot ready biodegradable0.9345
Rat acute toxicity2.1458 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9145
hERG inhibition (predictor II)Non-inhibitor0.9388
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000l-4590000000-29b707fca4dc920c7f33
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0fsr-0391000000-7b6ccc17a0c5b702b9fe
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-0090000000-0f1d6b067473da982f36
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0532-2090000000-ed945acc16be6ef92a74
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-016r-3890000000-f659f3fd924268ae091a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dr-6390000000-e690ddcfe4fd5dd3a542
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00b9-2940000000-4de2e96f04b2e9370002
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]-180.57219
predicted
DeepCCS 1.0 (2019)
[M+H]+182.93018
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.94432
predicted
DeepCCS 1.0 (2019)

Carriers

Details1. Cellular retinoic acid-binding protein 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Transports retinoic acid to the nucleus. Regulates the access of retinoic acid to the nuclear retinoic acid receptors.
Gene Name
CRABP2
Uniprot ID
P29373
Uniprot Name
Cellular retinoic acid-binding protein 2
Molecular Weight
15692.925 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 21:32 / Updated at June 12, 2020 16:52