NAV

(5Z)-7-{(1R,4S,5R,6R)-6-[(1E)-1-Octen-1-yl]-2,3-diazabicyclo[2.2.1]hept-2-en-5-yl}-5-heptenoic acid

Identification

Generic Name
(5Z)-7-{(1R,4S,5R,6R)-6-[(1E)-1-Octen-1-yl]-2,3-diazabicyclo[2.2.1]hept-2-en-5-yl}-5-heptenoic acid
DrugBank Accession Number
DB08675
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 332.4803
Monoisotopic: 332.246378278
Chemical Formula
C20H32N2O2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProstacyclin synthaseNot 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 long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Long-chain fatty acids
Alternative Parents
Heterocyclic fatty acids / Amino fatty acids / Unsaturated fatty acids / Azo compounds / Propargyl-type 1,3-dipolar organic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
Aliphatic heteropolycyclic compound / Amino fatty acid / Azacycle / Azo compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Heterocyclic fatty acid / Hydrocarbon derivative / Long-chain fatty acid
show 10 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
SRIZDZJPKIYUPZ-IDUFWMFESA-N
InChI
InChI=1S/C20H32N2O2/c1-2-3-4-5-6-9-12-16-17(19-15-18(16)21-22-19)13-10-7-8-11-14-20(23)24/h7,9-10,12,16-19H,2-6,8,11,13-15H2,1H3,(H,23,24)/b10-7-,12-9+/t16-,17-,18-,19+/m1/s1
IUPAC Name
(5Z)-7-[(1R,4S,5R,6R)-6-[(1E)-oct-1-en-1-yl]-2,3-diazabicyclo[2.2.1]hept-2-en-5-yl]hept-5-enoic acid
SMILES
[H]\C(CCCC(O)=O)=C(/[H])C[C@@]1([H])[C@]2([H])C[C@@]([H])(N=N2)[C@]1([H])C(\[H])=C(/[H])CCCCCC

References

General References
Not Available
PubChem Compound
94286438
PubChem Substance
99445146
ChemSpider
35034452
ZINC
ZINC000049872120
PDBe Ligand
U51
PDB Entries
3b99

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 Solubility0.000272 mg/mLALOGPS
logP6.03ALOGPS
logP5.07Chemaxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.39Chemaxon
pKa (Strongest Basic)1.13Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area62.02 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity99.23 m3·mol-1Chemaxon
Polarizability39.37 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9401
Caco-2 permeable-0.5082
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.7041
P-glycoprotein inhibitor IINon-inhibitor0.9673
Renal organic cation transporterNon-inhibitor0.7203
CYP450 2C9 substrateNon-substrate0.8342
CYP450 2D6 substrateNon-substrate0.7933
CYP450 3A4 substrateNon-substrate0.5802
CYP450 1A2 substrateNon-inhibitor0.7176
CYP450 2C9 inhibitorNon-inhibitor0.7791
CYP450 2D6 inhibitorNon-inhibitor0.9205
CYP450 2C19 inhibitorNon-inhibitor0.8109
CYP450 3A4 inhibitorNon-inhibitor0.9461
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9748
Ames testNon AMES toxic0.7119
CarcinogenicityNon-carcinogens0.8457
BiodegradationNot ready biodegradable0.9393
Rat acute toxicity2.3457 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8704
hERG inhibition (predictor II)Non-inhibitor0.9674
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-0019000000-bb2dff73b9a508b53628
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0019000000-5dbd867e4ec40bb98ac4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0159-1093000000-6acf7c5cd84611eb6ffe
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0039000000-04607e2090ca00ed48d4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0nmi-0093000000-ede3f3e0cb61d1547d62
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00us-6391000000-d87c444d1054c19294c0
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]-193.33862
predicted
DeepCCS 1.0 (2019)
[M+H]+195.16353
predicted
DeepCCS 1.0 (2019)
[M+Na]+200.76933
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Prostacyclin synthase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Prostaglandin-i synthase activity
Specific Function
Catalyzes the isomerization of prostaglandin H2 to prostacyclin (= prostaglandin I2).
Gene Name
PTGIS
Uniprot ID
Q16647
Uniprot Name
Prostacyclin synthase
Molecular Weight
57103.385 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 21:33 / Updated at June 12, 2020 16:52