Showing NP-Card for Phenylethylamine (NP0000779)

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Record Information
Version2.0
Created at2009-04-06 16:22:10 UTC
Updated at2024-09-17 15:42:58 UTC
NP-MRD IDNP0000779
Secondary Accession NumbersNone
Natural Product Identification
Common NamePhenylethylamine
Description
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000779 (Phenylethylamine)

  Mrv1652303202018592D          

  9  9  0  0  0  0            999 V2000
   13.9049  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9049  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8426  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4302  -14.1382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
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3D MOL for NP0000779 (Phenylethylamine)

HMDB0012275
     RDKit          3D
Phenylethylamine
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.0884    0.5367    1.4140 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075   -0.1311    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -1.1147   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129   -0.4661   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101    0.0401   -1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    0.6516   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.7394   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.2484    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8868   -0.3557    0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025   -0.0420    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    1.5034    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746   -0.6397    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.6504   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -1.5595   -1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -1.9178    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212   -0.0293   -2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    1.0529   -2.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688    1.2201   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    0.3389    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.7262    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
M  END
Download

3D SDF for NP0000779 (Phenylethylamine)

  Mrv1652303202018592D          

  9  9  0  0  0  0            999 V2000
   13.9049  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -11.2808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -11.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9049  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6675  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8426  -13.4243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0800  -12.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4302  -14.1382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  5  2  0  0  0  0
  4  8  2  0  0  0  0
  5  8  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000779

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2

> <INCHI_KEY>
BHHGXPLMPWCGHP-UHFFFAOYSA-N

> <FORMULA>
C8H11N

> <MOLECULAR_WEIGHT>
121.1796

> <EXACT_MASS>
121.089149357

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
14.346174019011707

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-phenylethan-1-amine

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.3876754570000003

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.791742642861854

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
39.28639999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-phenylethylamine

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0000779 (Phenylethylamine)

HMDB0012275
     RDKit          3D
Phenylethylamine
 20 20  0  0  0  0  0  0  0  0999 V2000
    2.0884    0.5367    1.4140 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3075   -0.1311    0.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2001   -1.1147   -0.1550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129   -0.4661   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6101    0.0401   -1.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8455    0.6516   -1.5246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5863    0.7394   -0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363    0.2484    0.8428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8868   -0.3557    0.8781 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7025   -0.0420    2.1636 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7674    1.5034    1.3538 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746   -0.6397    0.2002 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3795    0.6504   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -1.5595   -1.1555 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1987   -1.9178    0.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0212   -0.0293   -2.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2420    1.0529   -2.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688    1.2201   -0.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7561    0.3389    1.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5774   -0.7262    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  0
  3 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
M  END
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PDB for NP0000779 (Phenylethylamine)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0      25.956 -21.057   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      24.416 -21.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.726 -22.391   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.646 -22.391   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.956 -23.725   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.646 -25.059   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.106 -25.059   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.416 -23.725   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      21.336 -26.391   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3    8                                                       
CONECT    6    7    8                                                       
CONECT    7    6    9                                                       
CONECT    8    4    5    6                                                  
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   18    0
END
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3D PDB for NP0000779 (Phenylethylamine)

COMPND    HMDB0012275
HETATM    1  N1  UNL     1       2.088   0.537   1.414  1.00  0.00           N  
HETATM    2  C1  UNL     1       2.307  -0.131   0.167  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.200  -1.115  -0.155  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.113  -0.466  -0.252  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.610   0.040  -1.428  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.845   0.652  -1.525  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.586   0.739  -0.364  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.136   0.248   0.843  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.887  -0.356   0.878  1.00  0.00           C  
HETATM   10  H1  UNL     1       1.702  -0.042   2.164  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.767   1.503   1.354  1.00  0.00           H  
HETATM   12  H3  UNL     1       3.275  -0.640   0.200  1.00  0.00           H  
HETATM   13  H4  UNL     1       2.380   0.650  -0.623  1.00  0.00           H  
HETATM   14  H5  UNL     1       1.425  -1.559  -1.156  1.00  0.00           H  
HETATM   15  H6  UNL     1       1.199  -1.918   0.596  1.00  0.00           H  
HETATM   16  H7  UNL     1      -0.021  -0.029  -2.352  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.242   1.053  -2.451  1.00  0.00           H  
HETATM   18  H9  UNL     1      -3.569   1.220  -0.417  1.00  0.00           H  
HETATM   19  H10 UNL     1      -2.756   0.339   1.739  1.00  0.00           H  
HETATM   20  H11 UNL     1      -0.577  -0.726   1.852  1.00  0.00           H  
CONECT    1    2   10   11
CONECT    2    3   12   13
CONECT    3    4   14   15
CONECT    4    5    5    9
CONECT    5    6   16
CONECT    6    7    7   17
CONECT    7    8   18
CONECT    8    9    9   19
CONECT    9   20
END
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SMILES for NP0000779 (Phenylethylamine)

NCCC1=CC=CC=C1
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INCHI for NP0000779 (Phenylethylamine)

InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
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View in JSmolView NMR Assignments
Synonyms
Chemical FormulaC8H11N
Average Mass121.1796 Da
Monoisotopic Mass121.08915 Da
IUPAC Name2-phenylethan-1-amine
Traditional Name2-phenylethylamine
CAS Registry Number64-04-0
SMILES
NCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
InChI KeyBHHGXPLMPWCGHP-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species Where Detected
Species NameSourceReference
Pseudomonas pseudoalcaligenesKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • 2-arylethylamine
  • Aralkylamine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Primary aliphatic amine
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point194.00 to 195.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility63250 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.410The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility2.19 g/LALOGPS
logP1.41ALOGPS
logP1.39ChemAxon
logS-1.7ALOGPS
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.02 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.29 m³·mol⁻¹ChemAxon
Polarizability14.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012275
DrugBank IDDB04325
Phenol Explorer Compound IDNot Available
FoodDB IDFDB010580
KNApSAcK IDC00001426
Chemspider ID13856352
KEGG Compound IDC05332
BioCyc IDPHENYLETHYLAMINE
BiGG IDNot Available
Wikipedia Link2-phenylethylamine
METLIN IDNot Available
PubChem Compound1001
PDB IDNot Available
ChEBI ID18397
Good Scents IDrw1035561
References
General References
  1. Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4. [PubMed:12205654 ]
  2. O'Reilly RL, Davis BA: Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jan;18(1):63-75. [PubMed:7906896 ]
  3. Potkin SG, Wyatt RJ, Karoum F: Phenylethylamine (PEA) and phenylacetic acid (PAA) in the urine of chronic schizophrenic patients and controls. Psychopharmacol Bull. 1980 Jan;16(1):52-4. [PubMed:7360842 ]
  4. Ferrero DM, Lemon JK, Fluegge D, Pashkovski SL, Korzan WJ, Datta SR, Spehr M, Fendt M, Liberles SD: Detection and avoidance of a carnivore odor by prey. Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11235-40. doi: 10.1073/pnas.1103317108. Epub 2011 Jun 20. [PubMed:21690383 ]
  5. Kim B, Byun BY, Mah JH: Biogenic amine formation and bacterial contribution in Natto products. Food Chem. 2012 Dec 1;135(3):2005-11. doi: 10.1016/j.foodchem.2012.06.091. Epub 2012 Jul 3. [PubMed:22953951 ]
  6. Landete JM, Pardo I, Ferrer S: Tyramine and phenylethylamine production among lactic acid bacteria isolated from wine. Int J Food Microbiol. 2007 Apr 20;115(3):364-8. doi: 10.1016/j.ijfoodmicro.2006.10.051. Epub 2007 Jan 18. [PubMed:17307265 ]
  7. Marcobal A, de las Rivas B, Munoz R: First genetic characterization of a bacterial beta-phenylethylamine biosynthetic enzyme in Enterococcus faecium RM58. FEMS Microbiol Lett. 2006 May;258(1):144-9. doi: 10.1111/j.1574-6968.2006.00206.x. [PubMed:16630269 ]