NAV

(1R,4S,7AS)-1-(1-FORMYLPROP-1-EN-1-YL)-4-METHOXY-2,4,5,6,7,7A-HEXAHYDRO-1H-ISOINDOLE-3-CARBOXYLIC ACID

Identification

Generic Name
(1R,4S,7AS)-1-(1-FORMYLPROP-1-EN-1-YL)-4-METHOXY-2,4,5,6,7,7A-HEXAHYDRO-1H-ISOINDOLE-3-CARBOXYLIC ACID
DrugBank Accession Number
DB08110
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 265.305
Monoisotopic: 265.131408101
Chemical Formula
C14H19NO4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UBeta-lactamaseNot AvailableEnterobacter cloacae
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 alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids
Alternative Parents
Isoindoles / Pyrroline carboxylic acids / Enals / Amino acids / Monocarboxylic acids and derivatives / Enamines / Dialkylamines / Dialkyl ethers / Carboxylic acids / Azacyclic compounds
show 4 more
Substituents
Aldehyde / Aliphatic heteropolycyclic compound / Alpha,beta-unsaturated aldehyde / Alpha-amino acid / Amine / Amino acid / Azacycle / Carbonyl group / Carboxylic acid / Dialkyl ether
show 19 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
ZYKSDPVHVMSKIL-IIHMJNQGSA-N
InChI
InChI=1S/C14H19NO4/c1-3-8(7-16)12-9-5-4-6-10(19-2)11(9)13(15-12)14(17)18/h3,7,9-10,12,15H,4-6H2,1-2H3,(H,17,18)/b8-3-/t9-,10-,12-/m0/s1
IUPAC Name
(1R,4S,7aS)-4-methoxy-1-[(2E)-1-oxobut-2-en-2-yl]-2,4,5,6,7,7a-hexahydro-1H-isoindole-3-carboxylic acid
SMILES
[H][C@]1(NC(C(O)=O)=C2[C@]1([H])CCC[C@]2([H])OC)C(=C/C)\C=O

References

General References
Not Available
PubChem Compound
46937125
PubChem Substance
99444581
ChemSpider
26325636
ZINC
ZINC000100036348
PDBe Ligand
LK7
PDB Entries
2q9m

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 Solubility1.34 mg/mLALOGPS
logP1.65ALOGPS
logP0.62Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)5.56Chemaxon
pKa (Strongest Basic)0.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area75.63 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity71.63 m3·mol-1Chemaxon
Polarizability27.69 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8595
Blood Brain Barrier-0.8494
Caco-2 permeable-0.5995
P-glycoprotein substrateSubstrate0.6503
P-glycoprotein inhibitor INon-inhibitor0.7931
P-glycoprotein inhibitor IINon-inhibitor0.8786
Renal organic cation transporterNon-inhibitor0.8106
CYP450 2C9 substrateNon-substrate0.8405
CYP450 2D6 substrateNon-substrate0.8212
CYP450 3A4 substrateSubstrate0.6172
CYP450 1A2 substrateNon-inhibitor0.5335
CYP450 2C9 inhibitorNon-inhibitor0.8046
CYP450 2D6 inhibitorNon-inhibitor0.8912
CYP450 2C19 inhibitorNon-inhibitor0.8596
CYP450 3A4 inhibitorNon-inhibitor0.9661
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9058
Ames testNon AMES toxic0.6581
CarcinogenicityNon-carcinogens0.9851
BiodegradationNot ready biodegradable0.5556
Rat acute toxicity2.5797 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8682
hERG inhibition (predictor II)Non-inhibitor0.8871
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-MSsplash10-05a9-5390000000-931e9f65b3e4eaafc8e0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0090000000-215ecd33eb0355871ea1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0090000000-32bb74a5ab164c3ec880
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014j-0190000000-62706a8731ea9d6410a9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0290000000-67b046a1e70c7cb69667
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-090r-3940000000-d2beca9eead3ab7fab46
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-3920000000-982a4cb27ec6b6a993c7
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]-160.25642
predicted
DeepCCS 1.0 (2019)
[M+H]+162.65198
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.35457
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Beta-lactamase
Kind
Protein
Organism
Enterobacter cloacae
Pharmacological action
Unknown
General Function
Beta-lactamase activity
Specific Function
This protein is a serine beta-lactamase with a substrate specificity for cephalosporins.
Gene Name
ampC
Uniprot ID
P05364
Uniprot Name
Beta-lactamase
Molecular Weight
41301.33 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 21:28 / Updated at June 12, 2020 16:52