NAV

(1r)-4-[(1e,3e,5e,7z,9e,11z,13e,15e)-17-Hydroxy-3,7,12,16-Tetramethylheptadeca-1,3,5,7,9,11,13,15-Octaen-1-Yl]-3,5,5-Trimethylcyclohex-3-En-1-Ol

Identification

Generic Name
(1r)-4-[(1e,3e,5e,7z,9e,11z,13e,15e)-17-Hydroxy-3,7,12,16-Tetramethylheptadeca-1,3,5,7,9,11,13,15-Octaen-1-Yl]-3,5,5-Trimethylcyclohex-3-En-1-Ol
DrugBank Accession Number
DB02253
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 434.6533
Monoisotopic: 434.318480588
Chemical Formula
C30H42O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UApocarotenoid-15,15'-oxygenaseNot AvailableSynechocystis sp. (strain PCC 6803 / Kazusa)
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 triterpenoids. These are terpene molecules containing six isoprene units.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Triterpenoids
Direct Parent
Triterpenoids
Alternative Parents
Long-chain fatty alcohols / Secondary alcohols / Primary alcohols / Hydrocarbon derivatives
Substituents
Alcohol / Aliphatic homomonocyclic compound / Fatty acyl / Fatty alcohol / Hydrocarbon derivative / Long chain fatty alcohol / Organic oxygen compound / Organooxygen compound / Primary alcohol / Secondary alcohol
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FNAJVVMDXCOSFY-VFGOXHQXSA-N
InChI
InChI=1S/C30H42O2/c1-23(12-8-9-13-24(2)15-11-17-26(4)22-31)14-10-16-25(3)18-19-29-27(5)20-28(32)21-30(29,6)7/h8-19,28,31-32H,20-22H2,1-7H3/b9-8+,14-10+,15-11+,19-18+,23-12-,24-13-,25-16+,26-17+/t28-/m1/s1
IUPAC Name
(1R)-4-[(1E,3E,5E,7Z,9E,11Z,13E,15E)-17-hydroxy-3,7,12,16-tetramethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol
SMILES
OC\C(C)=C\C=C\C(\C)=C/C=C/C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)C[C@@H](O)CC1(C)C

References

General References
Not Available
PubChem Compound
5287502
PubChem Substance
46506703
ChemSpider
4449866
ChEBI
39930
ZINC
ZINC000012501797
PDBe Ligand
3ON
PDB Entries
2biw

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 Solubility0.00157 mg/mLALOGPS
logP6.84ALOGPS
logP5.9Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)16.76Chemaxon
pKa (Strongest Basic)-1.1Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity149.43 m3·mol-1Chemaxon
Polarizability55.26 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9965
Blood Brain Barrier+0.7069
Caco-2 permeable+0.716
P-glycoprotein substrateNon-substrate0.551
P-glycoprotein inhibitor INon-inhibitor0.6358
P-glycoprotein inhibitor IINon-inhibitor0.7671
Renal organic cation transporterNon-inhibitor0.8679
CYP450 2C9 substrateNon-substrate0.8596
CYP450 2D6 substrateNon-substrate0.8233
CYP450 3A4 substrateSubstrate0.5917
CYP450 1A2 substrateNon-inhibitor0.8414
CYP450 2C9 inhibitorNon-inhibitor0.9015
CYP450 2D6 inhibitorNon-inhibitor0.9263
CYP450 2C19 inhibitorNon-inhibitor0.7317
CYP450 3A4 inhibitorNon-inhibitor0.7756
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7775
Ames testNon AMES toxic0.6188
CarcinogenicityNon-carcinogens0.7546
BiodegradationNot ready biodegradable0.6987
Rat acute toxicity2.0310 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8922
hERG inhibition (predictor II)Non-inhibitor0.8802
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/MSsplash10-01ot-0029100000-bdd8bdcc880ea36f4e6c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0004900000-16514e32f34769187715
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0139500000-3bf82e33f6b9388dd81c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00l2-1019000000-28471faa1184520ddab2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kga-0259000000-4d6d3bae29a3c9c36e81
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004s-0196000000-8d9993d86ee83b142e18
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]-230.23479
predicted
DeepCCS 1.0 (2019)
[M+H]+232.15427
predicted
DeepCCS 1.0 (2019)
[M+Na]+238.05406
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Apocarotenoid-15,15'-oxygenase
Kind
Protein
Organism
Synechocystis sp. (strain PCC 6803 / Kazusa)
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Cleaves a number of carotenals and carotenols in the all-trans configuration at the 15-15' double bond producing retinal or retinol, respectively. Also shows activity toward lycopenals and the corr...
Gene Name
Not Available
Uniprot ID
P74334
Uniprot Name
Apocarotenoid-15,15'-oxygenase
Molecular Weight
54286.065 Da

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52