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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

enzymes (2) Show 2 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:45 UTC

HMDB ID

HMDB0014830

Secondary Accession Numbers

HMDB14830

Metabolite Identification

Common Name

Phentolamine

Description

Phentolamine is only found in individuals that have used or taken this drug. It is a nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of raynaud disease and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease (PubChem). Phentolamine produces its therapeutic actions by competitively blocking alpha-adrenergic receptors (primarily excitatory responses of smooth muscle and exocrine glands), leading to a muscle relaxation and a widening of the blood vessels. This widening of the blood vessels results in a lowering of blood pressure. The action of phentolamine on the alpha adrenergic receptors is relatively transient and the blocking effect is incomplete. The drug is more effective in antagonizing responses to circulating epinephrine and/or norepinephrine than in antagonizing responses to mediator released at the adrenergic nerve ending. Phentolamine also stimulates β-adrenergic receptors and produces a positive inotropic and chronotropic effect on the heart and increases cardiac output.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0014830
     RDKit          3D
Phentolamine
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.4480   -2.5036   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1851   -1.7321    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472   -2.1995    0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -1.4549    1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952   -0.2357    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712    0.5585    0.4983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547    0.1561    1.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961   -1.0734    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -2.0827    1.4567 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310   -3.1255    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -2.3996   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681   -1.3304   -0.6356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615    1.8468   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.0262   -1.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403    3.2805   -1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058    4.3495   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1038    4.2106    0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5324    5.2970    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    2.9514    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    0.2160   -0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0033   -0.5097   -0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3764   -3.2071   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -3.0381    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576   -1.7415   -0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -3.1502    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045   -1.8513    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    0.0654    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247    0.9853    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023   -3.9059    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -3.5363    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5697   -2.0287   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478   -3.0904   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2003   -0.8369   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    1.1910   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0679    3.3764   -3.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950    5.3344   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    5.2632    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4027    2.8605    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824    1.1813   -0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930   -0.1168   -1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 12  8  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

692
  Mrv0541 02231214562D          

 21 23  0  0  0  0            999 V2000
    2.0894   -2.2353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185    0.2398    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1365    1.9622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    1.9622    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040    1.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3915    2.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2165    2.7468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329    0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -0.5853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    0.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329    1.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040   -0.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329   -0.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6619    1.4773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6619    0.6523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9474    1.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8040   -1.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2329   -1.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5185   -2.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3764    1.8898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 18  1  0  0  0  0
  2  5  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  3  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  6  2  0  0  0  0
  4  8  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 10 14  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  2  0  0  0  0
 13 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 15 21  1  0  0  0  0
 18 20  2  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014830

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H19N3O/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15/h2-8,11,21H,9-10,12H2,1H3,(H,18,19)

> <INCHI_KEY>
MRBDMNSDAVCSSF-UHFFFAOYSA-N

> <FORMULA>
C17H19N3O

> <MOLECULAR_WEIGHT>
281.3523

> <EXACT_MASS>
281.152812245

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.366165054899653

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.5151081762943854

> <ALOGPS_LOGS>
-3.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.779238140625477

> <JCHEM_PKA_STRONGEST_BASIC>
9.018893958878193

> <JCHEM_POLAR_SURFACE_AREA>
47.86

> <JCHEM_REFRACTIVITY>
84.25130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phentolamine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014830
     RDKit          3D
Phentolamine
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.4480   -2.5036   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1851   -1.7321    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472   -2.1995    0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -1.4549    1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952   -0.2357    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712    0.5585    0.4983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547    0.1561    1.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961   -1.0734    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -2.0827    1.4567 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310   -3.1255    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -2.3996   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681   -1.3304   -0.6356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615    1.8468   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.0262   -1.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403    3.2805   -1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058    4.3495   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1038    4.2106    0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5324    5.2970    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    2.9514    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    0.2160   -0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0033   -0.5097   -0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3764   -3.2071   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -3.0381    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576   -1.7415   -0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -3.1502    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045   -1.8513    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    0.0654    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247    0.9853    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023   -3.9059    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -3.5363    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5697   -2.0287   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478   -3.0904   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2003   -0.8369   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    1.1910   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0679    3.3764   -3.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950    5.3344   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    5.2632    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4027    2.8605    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824    1.1813   -0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930   -0.1168   -1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 12  8  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 692                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.900  -4.173   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       6.568   0.448   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       3.988   3.663   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       6.480   3.663   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.234   1.218   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.234   2.758   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.464   5.127   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.004   5.127   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.901   1.218   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.568  -1.093   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.235   0.448   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.901   2.758   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.234  -1.863   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.901  -1.863   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.569   2.758   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.569   1.218   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.235   3.528   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.234  -3.403   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.901  -3.403   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.568  -4.173   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.903   3.528   0.000  0.00  0.00           C+0
CONECT    1   18                                                            
CONECT    2    5    9   10                                                  
CONECT    3    6    7                                                       
CONECT    4    6    8                                                       
CONECT    5    2    6                                                       
CONECT    6    3    4    5                                                  
CONECT    7    3    8                                                       
CONECT    8    4    7                                                       
CONECT    9    2   11   12                                                  
CONECT   10    2   13   14                                                  
CONECT   11    9   16                                                       
CONECT   12    9   17                                                       
CONECT   13   10   18                                                       
CONECT   14   10   19                                                       
CONECT   15   16   17   21                                                  
CONECT   16   11   15                                                       
CONECT   17   12   15                                                       
CONECT   18    1   13   20                                                  
CONECT   19   14   20                                                       
CONECT   20   18   19                                                       
CONECT   21   15                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0014830
HETATM    1  C1  UNL     1       4.448  -2.504  -0.100  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.185  -1.732   0.077  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.147  -2.199   0.856  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.979  -1.455   1.002  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.795  -0.236   0.392  1.00  0.00           C  
HETATM    6  N1  UNL     1      -0.371   0.559   0.498  1.00  0.00           N  
HETATM    7  C6  UNL     1      -1.555   0.156   1.205  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.196  -1.073   0.707  1.00  0.00           C  
HETATM    9  N2  UNL     1      -2.521  -2.083   1.457  1.00  0.00           N  
HETATM   10  C8  UNL     1      -3.131  -3.125   0.658  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.544  -2.400  -0.632  1.00  0.00           C  
HETATM   12  N3  UNL     1      -2.568  -1.330  -0.636  1.00  0.00           N  
HETATM   13  C10 UNL     1      -0.361   1.847  -0.119  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.764   2.026  -1.412  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.740   3.281  -1.979  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.306   4.350  -1.224  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.104   4.211   0.070  1.00  0.00           C  
HETATM   18  O1  UNL     1       0.532   5.297   0.797  1.00  0.00           O  
HETATM   19  C15 UNL     1       0.074   2.951   0.621  1.00  0.00           C  
HETATM   20  C16 UNL     1       1.865   0.216  -0.393  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.003  -0.510  -0.535  1.00  0.00           C  
HETATM   22  H1  UNL     1       4.376  -3.207  -0.961  1.00  0.00           H  
HETATM   23  H2  UNL     1       4.755  -3.038   0.819  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.258  -1.741  -0.279  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.277  -3.150   1.338  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.205  -1.851   1.618  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.311   0.065   2.308  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.325   0.985   1.209  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.402  -3.906   0.372  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.041  -3.536   1.111  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.570  -2.029  -0.509  1.00  0.00           H  
HETATM   32  H11 UNL     1      -3.448  -3.090  -1.486  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.200  -0.837  -1.465  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.108   1.191  -2.023  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.068   3.376  -3.005  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.295   5.334  -1.693  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.844   5.263   1.744  1.00  0.00           H  
HETATM   38  H17 UNL     1       0.403   2.860   1.648  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.782   1.181  -0.907  1.00  0.00           H  
HETATM   40  H19 UNL     1       3.793  -0.117  -1.150  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   21
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   20
CONECT    6    7   13
CONECT    7    8   27   28
CONECT    8    9    9   12
CONECT    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   33
CONECT   13   14   14   19
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   36
CONECT   17   18   19   19
CONECT   18   37
CONECT   19   38
CONECT   20   21   21   39
CONECT   21   40
END

HMDB0014830
     RDKit          3D
Phentolamine
 40 42  0  0  0  0  0  0  0  0999 V2000
    4.4480   -2.5036   -0.1004 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1851   -1.7321    0.0774 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1472   -2.1995    0.8559 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9795   -1.4549    1.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952   -0.2357    0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3712    0.5585    0.4983 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5547    0.1561    1.2046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1961   -1.0734    0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5212   -2.0827    1.4567 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1310   -3.1255    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5440   -2.3996   -0.6318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5681   -1.3304   -0.6356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3615    1.8468   -0.1188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7639    2.0262   -1.4120 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403    3.2805   -1.9786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058    4.3495   -1.2237 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1038    4.2106    0.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5324    5.2970    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0742    2.9514    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    0.2160   -0.3928 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0033   -0.5097   -0.5353 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3764   -3.2071   -0.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7550   -3.0381    0.8190 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2576   -1.7415   -0.2791 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2774   -3.1502    1.3379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2045   -1.8513    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    0.0654    2.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247    0.9853    1.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4023   -3.9059    0.3724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0413   -3.5363    1.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5697   -2.0287   -0.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4478   -3.0904   -1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2003   -0.8369   -1.4654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    1.1910   -2.0229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0679    3.3764   -3.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950    5.3344   -1.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8439    5.2632    1.7440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4027    2.8605    1.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7824    1.1813   -0.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7930   -0.1168   -1.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  6 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
  5 20  1  0
 20 21  2  0
 21  2  1  0
 12  8  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 18 37  1  0
 19 38  1  0
 20 39  1  0
 21 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-(N-(m-Hydroxyphenyl)-p-toluidinomethyl)imidazoline	ChEBI
Fentolamina	ChEBI
Phentolamine mesylate	ChEBI
Phentolaminum	ChEBI
Regitina	ChEBI
Regitine	ChEBI
Rogitine	ChEBI
Phentolamine mesylic acid	Generator
Regityn	HMDB
Novartis brand OF phentolamine mesylate	HMDB
Paladin brand OF phentolamine mesylate	HMDB
Phentolamine mono hydrochloride	HMDB
Phentolamine mono-hydrochloride	HMDB
Alliance brand OF phentolamine mesylate	HMDB
Mesilate, phentolamine	HMDB
Mesylate, phentolamine	HMDB
Phentolamine methanesulfonate	HMDB
Schering-plough brand OF phentolamine mesylate	HMDB
Fentolamin	HMDB
Methanesulfonate, phentolamine	HMDB
mono-Hydrochloride, phentolamine	HMDB
Phentolamine mesilate	HMDB
Z-Max	HMDB

Chemical Formula

C₁₇H₁₉N₃O

Average Molecular Weight

281.3523

Monoisotopic Molecular Weight

281.152812245

IUPAC Name

3-[(4,5-dihydro-1H-imidazol-2-ylmethyl)(4-methylphenyl)amino]phenol

Traditional Name

phentolamine

CAS Registry Number

50-60-2

SMILES

CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C17H19N3O/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15/h2-8,11,21H,9-10,12H2,1H3,(H,18,19)

InChI Key

MRBDMNSDAVCSSF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyldiarylamines. These are tertiary alkylarylamines having two aryl and one alkyl groups attached to the amino group.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

Alkyldiarylamines

Alternative Parents

Substituents

Alkyldiarylamine
M-aminophenol
Aminophenol
Aminotoluene
Aniline or substituted anilines
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Monocyclic benzene moiety
Imidolactam
Benzenoid
2-imidazoline
Amidine
Carboxylic acid amidine
Azacycle
Organoheterocyclic compound
Carboximidamide
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organopnictogen compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:8081 )
substituted aniline (CHEBI:8081 )
imidazoles (CHEBI:8081 )
phenols (CHEBI:8081 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014830)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.27 g/L	Not Available
LogP	3.3	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	172.07	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000706

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.27 g/L	ALOGPS
logP	2.91	ALOGPS
logP	2.52	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	9.78	ChemAxon
pKa (Strongest Basic)	9.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	47.86 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.25 m³·mol⁻¹	ChemAxon
Polarizability	31.37 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	166.896	31661259
DarkChem	[M-H]-	170.396	31661259
DeepCCS	[M+H]+	165.081	30932474
DeepCCS	[M-H]-	162.723	30932474
DeepCCS	[M-2H]-	195.683	30932474
DeepCCS	[M+Na]+	171.174	30932474
AllCCS	[M+H]+	166.2	32859911
AllCCS	[M+H-H2O]+	162.6	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	170.4	32859911
AllCCS	[M+HCOO]-	170.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phentolamine	CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1	3598.0	Standard polar	33892256
Phentolamine	CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1	2442.9	Standard non polar	33892256
Phentolamine	CC1=CC=C(C=C1)N(CC1=NCCN1)C1=CC(O)=CC=C1	2815.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phentolamine,1TMS,isomer #1	CC1=CC=C(N(CC2=NCCN2)C2=CC=CC(O[Si](C)(C)C)=C2)C=C1	2685.2	Semi standard non polar	33892256
Phentolamine,1TMS,isomer #2	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C)C2=CC=CC(O)=C2)C=C1	2726.7	Semi standard non polar	33892256
Phentolamine,2TMS,isomer #1	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2)C=C1	2749.7	Semi standard non polar	33892256
Phentolamine,2TMS,isomer #1	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2)C=C1	2791.8	Standard non polar	33892256
Phentolamine,2TMS,isomer #1	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C)C2=CC=CC(O[Si](C)(C)C)=C2)C=C1	3599.6	Standard polar	33892256
Phentolamine,1TBDMS,isomer #1	CC1=CC=C(N(CC2=NCCN2)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	2899.7	Semi standard non polar	33892256
Phentolamine,1TBDMS,isomer #2	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C(C)(C)C)C2=CC=CC(O)=C2)C=C1	2978.0	Semi standard non polar	33892256
Phentolamine,2TBDMS,isomer #1	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3156.4	Semi standard non polar	33892256
Phentolamine,2TBDMS,isomer #1	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3234.2	Standard non polar	33892256
Phentolamine,2TBDMS,isomer #1	CC1=CC=C(N(CC2=NCCN2[Si](C)(C)C(C)(C)C)C2=CC=CC(O[Si](C)(C)C(C)(C)C)=C2)C=C1	3716.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Phentolamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2950000000-98d994688cae92ea0a0b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phentolamine GC-MS (1 TMS) - 70eV, Positive	splash10-0072-7953000000-578fe075a00a7a4d02b0	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phentolamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phentolamine , positive-QTOF	splash10-03di-4890000000-37817fa5f0f18f71350d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 10V, Positive-QTOF	splash10-001i-0090000000-f5257bc5fc7ab80d6c86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 20V, Positive-QTOF	splash10-001i-6190000000-51ab45cfce6d6cf7bc94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 40V, Positive-QTOF	splash10-0znd-7920000000-bcc3e60235210d193abc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 10V, Negative-QTOF	splash10-001i-0090000000-39ce2b3898232204803d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 20V, Negative-QTOF	splash10-001i-1190000000-18c4ef9ee29cd0bea9d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 40V, Negative-QTOF	splash10-0007-9650000000-7b0c9ea52c5b916cb6c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 10V, Positive-QTOF	splash10-001i-0090000000-0db20202647f4f8a9de6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 20V, Positive-QTOF	splash10-001i-1090000000-83d909204d9b8366fffc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 40V, Positive-QTOF	splash10-008c-7960000000-dcf271875addd4ab9fbd	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 10V, Negative-QTOF	splash10-001i-0090000000-18e93f9625f62017f8e6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 20V, Negative-QTOF	splash10-0002-0930000000-b6e55971aac85aabe446	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phentolamine 40V, Negative-QTOF	splash10-006t-0900000000-52d5bc155c2a85191934	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00692	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00692	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00692

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phentolamine

METLIN ID

Not Available

PubChem Compound

5775

PDB ID

Not Available

ChEBI ID

8081

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

References

Polak J, Moro C, Klimcakova E, Hejnova J, Majercik M, Viguerie N, Langin D, Lafontan M, Stich V, Berlan M: Dynamic strength training improves insulin sensitivity and functional balance between adrenergic alpha 2A and beta pathways in subcutaneous adipose tissue of obese subjects. Diabetologia. 2005 Dec;48(12):2631-40. Epub 2005 Nov 5. [PubMed:16273345 ]
Molderings GJ, Bonisch H, Bruss M, Likungu J, Gothert M: Species-specific pharmacological properties of human alpha(2A)-adrenoceptors. Hypertension. 2000 Sep;36(3):405-10. [PubMed:10988273 ]
Vonend O, Habbel S, Stegbauer J, Roth J, Hein L, Rump LC: Alpha(2A)-adrenoceptors regulate sympathetic transmitter release in mice kidneys. Br J Pharmacol. 2007 Jan;150(1):121-7. Epub 2006 Nov 20. [PubMed:17115069 ]
Trendelenburg AU, Meyer A, Klebroff W, Guimaraes S, Starke K: Crosstalk between presynaptic angiotensin receptors, bradykinin receptors and alpha 2-autoreceptors in sympathetic neurons: a study in alpha 2-adrenoceptor-deficient mice. Br J Pharmacol. 2003 Apr;138(8):1389-402. [PubMed:12721093 ]
Blandizzi C, Fornai M, Colucci R, Baschiera F, Barbara G, De Giorgio R, De Ponti F, Breschi MC, Del Tacca M: Altered prejunctional modulation of intestinal cholinergic and noradrenergic pathways by alpha2-adrenoceptors in the presence of experimental colitis. Br J Pharmacol. 2003 May;139(2):309-20. [PubMed:12770936 ]
Giussani DA, Moore PJ, Bennet L, Spencer JA, Hanson MA: Alpha 1- and alpha 2-adrenoreceptor actions of phentolamine and prazosin on breathing movements in fetal sheep in utero. J Physiol. 1995 Jul 1;486 ( Pt 1):249-55. [PubMed:7562640 ]
Bylund DB: Subtypes of alpha 1- and alpha 2-adrenergic receptors. FASEB J. 1992 Feb 1;6(3):832-9. [PubMed:1346768 ]
Saeed M, Sommer O, Holtz J, Bassenge E: Alpha-adrenoceptor blockade by phentolamine causes beta-adrenergic vasodilation by increased catecholamine release due to presynaptic alpha-blockade. J Cardiovasc Pharmacol. 1982 Jan-Feb;4(1):44-52. [PubMed:6176798 ]

Enzyme Details

2. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

References

Giussani DA, Moore PJ, Bennet L, Spencer JA, Hanson MA: Alpha 1- and alpha 2-adrenoreceptor actions of phentolamine and prazosin on breathing movements in fetal sheep in utero. J Physiol. 1995 Jul 1;486 ( Pt 1):249-55. [PubMed:7562640 ]
Bylund DB: Subtypes of alpha 1- and alpha 2-adrenergic receptors. FASEB J. 1992 Feb 1;6(3):832-9. [PubMed:1346768 ]
Saeed M, Sommer O, Holtz J, Bassenge E: Alpha-adrenoceptor blockade by phentolamine causes beta-adrenergic vasodilation by increased catecholamine release due to presynaptic alpha-blockade. J Cardiovasc Pharmacol. 1982 Jan-Feb;4(1):44-52. [PubMed:6176798 ]

Showing metabocard for Phentolamine (HMDB0014830)

MOL for HMDB0014830 (Phentolamine)

3D MOL for HMDB0014830 (Phentolamine)

3D SDF for HMDB0014830 (Phentolamine)

3D-SDF for HMDB0014830 (Phentolamine)

PDB for HMDB0014830 (Phentolamine)

3D PDB for HMDB0014830 (Phentolamine)

SMILES for HMDB0014830 (Phentolamine)

INCHI for HMDB0014830 (Phentolamine)

Structure for HMDB0014830 (Phentolamine)

3D Structure for HMDB0014830 (Phentolamine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References