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5-Hydroxy-N-Propargyl-1(R)-Aminoindan

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Identification

Generic Name
5-Hydroxy-N-Propargyl-1(R)-Aminoindan
DrugBank Accession Number
DB04307
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 187.2377
Monoisotopic: 187.099714043
Chemical Formula
C12H13NO
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UAmine oxidase [flavin-containing] B
ligand
Humans
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 indanes. These are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Indanes
Sub Class
Not Available
Direct Parent
Indanes
Alternative Parents
Aralkylamines / 1-hydroxy-2-unsubstituted benzenoids / Dialkylamines / Acetylides / Organopnictogen compounds / Organooxygen compounds / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / Acetylide / Amine / Aralkylamine / Aromatic homopolycyclic compound / Hydrocarbon derivative / Indane / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
NRSDGDXUWMMUEV-GFCCVEGCSA-N
InChI
InChI=1S/C12H13NO/c1-2-7-13-12-6-4-9-3-5-10(14)8-11(9)12/h1,3,5,8,12-14H,4,6-7H2/t12-/m1/s1
IUPAC Name
(3R)-3-[(prop-2-yn-1-yl)amino]-2,3-dihydro-1H-inden-5-ol
SMILES
[H][C@]1(CCC2=CC=C(O)C=C12)NCC#C

References

General References
Not Available
PubChem Compound
5289289
PubChem Substance
46507374
ChemSpider
4451284
BindingDB
10799
ChEMBL
CHEMBL371428
PDBe Ligand
RHP
PDB Entries
1s3e

Clinical Trials

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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 Solubility0.0679 mg/mLALOGPS
logP1.32ALOGPS
logP1.89Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.72Chemaxon
pKa (Strongest Basic)7.92Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area32.26 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity56.45 m3·mol-1Chemaxon
Polarizability21.11 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9827
Blood Brain Barrier+0.9177
Caco-2 permeable-0.5597
P-glycoprotein substrateNon-substrate0.5465
P-glycoprotein inhibitor INon-inhibitor0.9494
P-glycoprotein inhibitor IINon-inhibitor0.7834
Renal organic cation transporterNon-inhibitor0.6479
CYP450 2C9 substrateNon-substrate0.7805
CYP450 2D6 substrateNon-substrate0.5776
CYP450 3A4 substrateNon-substrate0.6112
CYP450 1A2 substrateInhibitor0.8325
CYP450 2C9 inhibitorNon-inhibitor0.8291
CYP450 2D6 inhibitorInhibitor0.6574
CYP450 2C19 inhibitorNon-inhibitor0.7559
CYP450 3A4 inhibitorNon-inhibitor0.9017
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.5645
CarcinogenicityNon-carcinogens0.9108
BiodegradationNot ready biodegradable0.7622
Rat acute toxicity2.6077 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6087
hERG inhibition (predictor II)Non-inhibitor0.5989
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-MSsplash10-001i-2900000000-6007841cb6ef809231b2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0019-0900000000-43973abd48f8e85499f3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-3900000000-7da34d748ef46c1644ee
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-1900000000-1426a0ef5368da5e4459
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0540-0900000000-eadd145c1f7048571216
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f8c-2900000000-bcf2dc72103ffc0c9cfb
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000l-9600000000-eb47d43fcfc88b138408
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]-140.29137
predicted
DeepCCS 1.0 (2019)
[M+H]+142.68694
predicted
DeepCCS 1.0 (2019)
[M+Na]+148.8448
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Amine oxidase [flavin-containing] B
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Catalyzes the oxidative deamination of primary and some secondary amines such as neurotransmitters, and exogenous amines including the tertiary amine, neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), with concomitant reduction of oxygen to hydrogen peroxide and participates in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924). Preferentially degrades benzylamine and phenylethylamine (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924)
Specific Function
Aliphatic amine oxidase activity
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 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]

Enzymes

Details1. Amine oxidase [flavin-containing] B
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Catalyzes the oxidative deamination of primary and some secondary amines such as neurotransmitters, and exogenous amines including the tertiary amine, neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), with concomitant reduction of oxygen to hydrogen peroxide and participates in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924). Preferentially degrades benzylamine and phenylethylamine (PubMed:11049757, PubMed:11134050, PubMed:20493079, PubMed:8316221, PubMed:8665924)
Specific Function
Aliphatic amine oxidase activity
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52