Showing NP-Card for Epinephrine (NP0000300)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:38:54 UTC
NP-MRD IDNP0000300
Secondary Accession NumbersNone
Natural Product Identification
Common NameEpinephrine
DescriptionEpinephrine is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. It is the active sympathomimetic hormone secreted from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. Epinephrine also constricts arterioles in the skin and gut while dilating arterioles in leg muscles. It elevates the blood sugar level by increasing hydrolysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in adipocytes. Epinephrine has a suppressive effect on the immune system.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000300 (Epinephrine)

  Mrv1652303182019232D          

 13 13  0  0  1  0            999 V2000
   -1.3740   -0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550   -0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595    0.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884   -1.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    0.5077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4839    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    1.3327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.5077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  7  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  9  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
  9 11  1  1  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
M  END
Download

3D MOL for NP0000300 (Epinephrine)

HMDB0000068
     RDKit          3D
Epinephrine
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.6910    0.6276   -0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -0.4106    0.2778 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -0.2512    0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9912   -0.4711   -0.7309 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3740    0.4390   -1.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779   -0.3962   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316   -1.5504   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5968   -1.4497   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2244   -0.2192   -0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5715   -0.0622    0.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353    0.9082   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0498    2.1645   -0.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0742    0.8543   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631    0.8120   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    1.5852   -0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038    0.3972   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4448   -1.3573   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927    0.7303    0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -1.0056    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -1.4960   -1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    1.0191   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7726   -2.5288   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283   -2.3272   -0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2484   -0.8045    0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5152    3.0193   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869    1.7732   -0.4890 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  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  6
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
M  END
Download

3D SDF for NP0000300 (Epinephrine)

  Mrv1652303182019232D          

 13 13  0  0  1  0            999 V2000
   -1.3740   -0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595   -1.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550   -0.7298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0550    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595    0.5077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3740    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884   -1.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0884    0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    0.5077    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4839    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7694    1.3327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1984    0.5077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9128    0.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  7  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  9  4  1  0  0  0  0
  6  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
  9 11  1  1  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000300

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNC[C@H](O)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1

> <INCHI_KEY>
UCTWMZQNUQWSLP-VIFPVBQESA-N

> <FORMULA>
C9H13NO3

> <MOLECULAR_WEIGHT>
183.2044

> <EXACT_MASS>
183.089543287

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.035703709071257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

> <ALOGPS_LOGP>
-0.82

> <JCHEM_LOGP>
-0.42952928501713206

> <ALOGPS_LOGS>
-0.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
12.652804138341846

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.694259402931468

> <JCHEM_PKA_STRONGEST_BASIC>
8.912171883219303

> <JCHEM_POLAR_SURFACE_AREA>
72.72

> <JCHEM_REFRACTIVITY>
49.2303

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
epinephrine

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000300 (Epinephrine)

HMDB0000068
     RDKit          3D
Epinephrine
 26 26  0  0  0  0  0  0  0  0999 V2000
    3.6910    0.6276   -0.5502 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1630   -0.4106    0.2778 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7550   -0.2512    0.5288 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9912   -0.4711   -0.7309 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3740    0.4390   -1.7003 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779   -0.3962   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2316   -1.5504   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5968   -1.4497   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2244   -0.2192   -0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5715   -0.0622    0.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4353    0.9082   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0498    2.1645   -0.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0742    0.8543   -0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631    0.8120   -0.2529 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610    1.5852   -0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038    0.3972   -1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4448   -1.3573   -0.0130 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5927    0.7303    0.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4164   -1.0056    1.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2207   -1.4960   -1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    1.0191   -2.0213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7726   -2.5288   -0.4943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2283   -2.3272   -0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2484   -0.8045    0.1798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5152    3.0193   -0.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4869    1.7732   -0.4890 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  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  6
  5 21  1  0
  7 22  1  0
  8 23  1  0
 10 24  1  0
 12 25  1  0
 13 26  1  0
M  END
Download

PDB for NP0000300 (Epinephrine)

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -2.565  -1.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.231  -2.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.103  -1.362   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.103   0.178   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.231   0.948   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.565   0.178   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.898  -2.132   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.898   0.948   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.436   0.948   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.770   0.178   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.436   2.488   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       4.104   0.948   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.437   0.178   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    1                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9   12                                                       
CONECT   11    9                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000300 (Epinephrine)

COMPND    HMDB0000068
HETATM    1  C1  UNL     1       3.691   0.628  -0.550  1.00  0.00           C  
HETATM    2  N1  UNL     1       3.163  -0.411   0.278  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.755  -0.251   0.529  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.991  -0.471  -0.731  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.374   0.439  -1.700  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.478  -0.396  -0.514  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.232  -1.550  -0.417  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.597  -1.450  -0.217  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.224  -0.219  -0.113  1.00  0.00           C  
HETATM   10  O2  UNL     1      -4.572  -0.062   0.084  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.435   0.908  -0.216  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.050   2.165  -0.114  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.074   0.854  -0.414  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.763   0.812  -0.253  1.00  0.00           H  
HETATM   15  H2  UNL     1       3.161   1.585  -0.344  1.00  0.00           H  
HETATM   16  H3  UNL     1       3.704   0.397  -1.637  1.00  0.00           H  
HETATM   17  H4  UNL     1       3.445  -1.357  -0.013  1.00  0.00           H  
HETATM   18  H5  UNL     1       1.593   0.730   0.988  1.00  0.00           H  
HETATM   19  H6  UNL     1       1.416  -1.006   1.270  1.00  0.00           H  
HETATM   20  H7  UNL     1       1.221  -1.496  -1.109  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.636   1.019  -2.021  1.00  0.00           H  
HETATM   22  H9  UNL     1      -0.773  -2.529  -0.494  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.228  -2.327  -0.134  1.00  0.00           H  
HETATM   24  H11 UNL     1      -5.248  -0.804   0.180  1.00  0.00           H  
HETATM   25  H12 UNL     1      -2.515   3.019  -0.181  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.487   1.773  -0.489  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5    6   20
CONECT    5   21
CONECT    6    7    7   13
CONECT    7    8   22
CONECT    8    9    9   23
CONECT    9   10   11
CONECT   10   24
CONECT   11   12   13   13
CONECT   12   25
CONECT   13   26
END
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SMILES for NP0000300 (Epinephrine)

CNC[C@H](O)C1=CC(O)=C(O)C=C1
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INCHI for NP0000300 (Epinephrine)

InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
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View in JSmol
Synonyms
Chemical FormulaC9H13NO3
Average Mass183.2044 Da
Monoisotopic Mass183.08954 Da
IUPAC Name4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Traditional Nameepinephrine
CAS Registry Number51-43-4
SMILES
CNC[C@H](O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1
InChI KeyUCTWMZQNUQWSLP-VIFPVBQESA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
Alternative Parents
Substituents
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Secondary amine
  • Secondary aliphatic amine
  • Aromatic alcohol
  • Alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point211.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.18 mg/mLNot Available
LogP-1.37Hansch, C. and Leo, A. Pomona College Medicinal Chemistry Project Claremont, CA Pomona College, July 1987. Log P Database, (C. Hansch and A. Leo), July 1987 edition.
Predicted Properties
PropertyValueSource
Water Solubility18.6 g/LALOGPS
logP-0.82ALOGPS
logP-0.43ChemAxon
logS-0.99ALOGPS
pKa (Strongest Acidic)9.69ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.23 m³·mol⁻¹ChemAxon
Polarizability19.04 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000068
DrugBank IDDB00668
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021889
KNApSAcK IDC00029643
Chemspider ID5611
KEGG Compound IDC00788
BioCyc IDL-EPINEPHRINE
BiGG ID35997
Wikipedia LinkEpinephrine
METLIN ID5127
PubChem Compound5816
PDB IDNot Available
ChEBI ID28918
Good Scents IDNot Available
References
General References