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3-Phenylpropylamine

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Identification

Generic Name
3-Phenylpropylamine
DrugBank Accession Number
DB04410
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 135.21
Monoisotopic: 135.104799423
Chemical Formula
C9H13N
Synonyms
  • 3-phenyl-1-aminopropane
  • 3-phenyl-1-propylamine
  • 3-phenyl-N-propylamine
  • 3-phenylpropanamine
  • benzenepropanamine
  • gamma-phenyl-n-propylamine
  • gamma-phenylpropylamine
  • hydrocinnamylamine
External IDs
  • NSC-87080
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine protease 1Not AvailableHumans
UTrypsin-2Not 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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylpropylamines
Direct Parent
Phenylpropylamines
Alternative Parents
Aralkylamines / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropylamine / Primary aliphatic amine / Primary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
P8326EZ31P
CAS number
2038-57-5
InChI Key
LYUQWQRTDLVQGA-UHFFFAOYSA-N
InChI
InChI=1S/C9H13N/c10-8-4-7-9-5-2-1-3-6-9/h1-3,5-6H,4,7-8,10H2
IUPAC Name
3-phenylpropan-1-amine
SMILES
NCCCC1=CC=CC=C1

References

Synthesis Reference

Zdravko Crnic, Srecko I. Kirin, "N-substituted derivatives of N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine and the procedure for their preparation." U.S. Patent US5618968, issued March, 1989.

US5618968
General References
Not Available
PubChem Compound
16259
PubChem Substance
46506901
ChemSpider
15427
BindingDB
50113826
ChEMBL
CHEMBL276864
ZINC
ZINC000001561633
PDBe Ligand
PRA
PDB Entries
1tnk / 1utl / 6wm1 / 7zgs

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 Solubility1.22 mg/mLALOGPS
logP1.76ALOGPS
logP1.83Chemaxon
logS-2ALOGPS
pKa (Strongest Basic)10.05Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area26.02 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity43.89 m3·mol-1Chemaxon
Polarizability16.41 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9374
Blood Brain Barrier+0.9466
Caco-2 permeable+0.8608
P-glycoprotein substrateNon-substrate0.7174
P-glycoprotein inhibitor INon-inhibitor0.9529
P-glycoprotein inhibitor IINon-inhibitor0.9338
Renal organic cation transporterNon-inhibitor0.5512
CYP450 2C9 substrateNon-substrate0.8488
CYP450 2D6 substrateSubstrate0.6953
CYP450 3A4 substrateNon-substrate0.7821
CYP450 1A2 substrateInhibitor0.7149
CYP450 2C9 inhibitorNon-inhibitor0.6848
CYP450 2D6 inhibitorInhibitor0.7589
CYP450 2C19 inhibitorInhibitor0.5282
CYP450 3A4 inhibitorNon-inhibitor0.8738
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7113
Ames testNon AMES toxic0.8933
CarcinogenicityNon-carcinogens0.8168
BiodegradationReady biodegradable0.9499
Rat acute toxicity2.2158 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6608
hERG inhibition (predictor II)Non-inhibitor0.8187
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-MSsplash10-001l-9100000000-dcdd82c8b0f8cf3506f6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-9700000000-5698bbac3057967af385
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-7cce736cfe9ccfed8444
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0900000000-90e10adfed7f59d06fdc
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f6x-9400000000-09a139a78860784a32ce
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-ffa76b08cc87233515ae
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9100000000-42baae93e3a6be444d1e
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]-131.088161
predicted
DarkChem Lite v0.1.0
[M-H]-126.03364
predicted
DeepCCS 1.0 (2019)
[M+H]+132.148161
predicted
DarkChem Lite v0.1.0
[M+H]+129.0729
predicted
DeepCCS 1.0 (2019)
[M+Na]+131.388861
predicted
DarkChem Lite v0.1.0
[M+Na]+137.87607
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine protease 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates
Specific Function
metal ion binding
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Serine protease 1
Molecular Weight
26557.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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]
Details2. Trypsin-2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
In the ileum, may be involved in defensin processing, including DEFA5
Specific Function
calcium ion binding
Gene Name
PRSS2
Uniprot ID
P07478
Uniprot Name
Trypsin-2
Molecular Weight
26487.55 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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