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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:40 UTC

HMDB ID

HMDB0014592

Secondary Accession Numbers

HMDB14592

Metabolite Identification

Common Name

Dipivefrin

Description

Dipivefrin is only found in individuals that have used or taken this drug. It is a prodrug of adrenaline, which is used to treat glaucoma. It is available as ophthalmic solution (eye drops). Dipivefrin is a prodrug with little or no pharmacologically activity until it is hydrolyzed into epinephrine inside the human eye. The liberated epinephrine, an adrenergic agonist, appears to exert its action by stimulating α- and/or β₂-adrenergic receptors, leading to a decrease in aqueous production and an enhancement of outflow facility. The dipivefrin prodrug delivery system is a more efficient way of delivering the therapeutic effects of epinephrine, with fewer side effects than are associated with conventional epinephrine therapy.

Structure

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

HMDB0014592
     RDKit          3D
Dipivefrin
 54 54  0  0  0  0  0  0  0  0999 V2000
    6.3825   -1.5808    2.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1413   -0.2284    1.6305 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606    0.0558    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.6634    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327   -2.0280    0.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9595   -0.1853   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    0.8026   -1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    1.2271   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.7174   -0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    1.2261   -1.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    2.2978   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    2.7631    0.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7699    2.8700   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    3.9751   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961    1.8737   -1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412    3.5455   -2.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504   -0.2472    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -0.7677    0.6653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -1.8965    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -2.4551   -0.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -2.4424    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388   -3.6842    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -2.6446    2.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -1.3876    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303   -0.6803    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0432   -1.5473    2.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4544   -2.1187    2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9785   -2.1273    1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7600   -0.0256    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1525   -0.2745    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777    1.1474    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0021   -0.2946   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -2.5038    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6090    1.2355   -1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    1.9896   -2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555    4.4067    0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    3.5513    0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7465    4.7195   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    2.4135   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1670    1.5615    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361    1.0529   -1.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    2.7953   -3.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    4.2763   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450    4.0591   -2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353   -3.6920    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141   -3.6639   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5492   -4.6089    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -1.6735    2.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617   -2.8522    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -3.4802    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -0.3777    0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029   -1.4571   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841   -1.5360    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629   -1.4382    1.0704 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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 17 25  2  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  7 34  1  0
  8 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
M  END

449
  Mrv0541 02231214412D          

 25 25  0  0  1  0            999 V2000
    5.2224    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.4751    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1120    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7620    2.4751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -3.3001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  1  0  0  0  0
  1 19  1  0  0  0  0
  2 18  1  0  0  0  0
  2 20  1  0  0  0  0
  3 10  1  0  0  0  0
  4 14  2  0  0  0  0
  5 18  2  0  0  0  0
  6 22  1  0  0  0  0
  6 25  1  0  0  0  0
  7 11  1  0  0  0  0
  7 12  1  0  0  0  0
  7 13  1  0  0  0  0
  7 14  1  0  0  0  0
  8 15  1  0  0  0  0
  8 16  1  0  0  0  0
  8 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 10  1  0  0  0  0
  9 21  2  0  0  0  0
  9 23  1  0  0  0  0
 10 22  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014592

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3

> <INCHI_KEY>
OCUJLLGVOUDECM-UHFFFAOYSA-N

> <FORMULA>
C19H29NO5

> <MOLECULAR_WEIGHT>
351.4373

> <EXACT_MASS>
351.204573043

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.6466263123802

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate

> <ALOGPS_LOGP>
3.17

> <JCHEM_LOGP>
3.714854507000001

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.000170168929397

> <JCHEM_PKA_STRONGEST_BASIC>
9.327951960406976

> <JCHEM_POLAR_SURFACE_AREA>
84.86

> <JCHEM_REFRACTIVITY>
94.93809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dipivefrin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014592
     RDKit          3D
Dipivefrin
 54 54  0  0  0  0  0  0  0  0999 V2000
    6.3825   -1.5808    2.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1413   -0.2284    1.6305 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606    0.0558    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.6634    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327   -2.0280    0.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9595   -0.1853   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    0.8026   -1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    1.2271   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.7174   -0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    1.2261   -1.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    2.2978   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    2.7631    0.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7699    2.8700   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    3.9751   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961    1.8737   -1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412    3.5455   -2.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504   -0.2472    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -0.7677    0.6653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -1.8965    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -2.4551   -0.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -2.4424    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388   -3.6842    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -2.6446    2.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -1.3876    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303   -0.6803    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0432   -1.5473    2.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4544   -2.1187    2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9785   -2.1273    1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7600   -0.0256    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1525   -0.2745    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777    1.1474    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0021   -0.2946   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -2.5038    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6090    1.2355   -1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    1.9896   -2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555    4.4067    0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    3.5513    0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7465    4.7195   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    2.4135   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1670    1.5615    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361    1.0529   -1.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    2.7953   -3.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    4.2763   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450    4.0591   -2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353   -3.6920    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141   -3.6639   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5492   -4.6089    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -1.6735    2.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617   -2.8522    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -3.4802    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -0.3777    0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029   -1.4571   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841   -1.5360    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629   -1.4382    1.0704 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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 17 25  2  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  7 34  1  0
  8 35  1  0
 14 36  1  0
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 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 449                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.748   2.310   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       7.081   0.770   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      13.750  -1.540   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      12.416   2.310   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       5.748  -1.540   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      13.750  -4.620   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      11.082   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.082  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.416  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.542   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.622   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.082   6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.082   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.644  -0.564   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.748   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748   0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082   0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.416  -3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.748  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      13.750  -6.160   0.000  0.00  0.00           C+0
CONECT    1   14   19                                                       
CONECT    2   18   20                                                       
CONECT    3   10                                                            
CONECT    4   14                                                            
CONECT    5   18                                                            
CONECT    6   22   25                                                       
CONECT    7   11   12   13   14                                             
CONECT    8   15   16   17   18                                             
CONECT    9   10   21   23                                                  
CONECT   10    3    9   22                                                  
CONECT   11    7                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    1    4    7                                                  
CONECT   15    8                                                            
CONECT   16    8                                                            
CONECT   17    8                                                            
CONECT   18    2    5    8                                                  
CONECT   19    1   20   21                                                  
CONECT   20    2   19   24                                                  
CONECT   21    9   19                                                       
CONECT   22    6   10                                                       
CONECT   23    9   24                                                       
CONECT   24   20   23                                                       
CONECT   25    6                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

COMPND    HMDB0014592
HETATM    1  C1  UNL     1       6.382  -1.581   2.038  1.00  0.00           C  
HETATM    2  N1  UNL     1       6.141  -0.228   1.631  1.00  0.00           N  
HETATM    3  C2  UNL     1       4.761   0.056   1.304  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.325  -0.663   0.041  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.433  -2.028   0.150  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.959  -0.185  -0.291  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.756   0.803  -1.260  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.477   1.227  -1.550  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.362   0.717  -0.922  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.880   1.226  -1.299  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.476   2.298  -0.630  1.00  0.00           C  
HETATM   12  O3  UNL     1      -0.811   2.763   0.331  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.770   2.870  -0.985  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.105   3.975  -0.006  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.896   1.874  -1.020  1.00  0.00           C  
HETATM   16  C12 UNL     1      -2.741   3.546  -2.362  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.550  -0.247   0.025  1.00  0.00           C  
HETATM   18  O4  UNL     1      -0.571  -0.768   0.665  1.00  0.00           O  
HETATM   19  C14 UNL     1      -1.237  -1.896   0.222  1.00  0.00           C  
HETATM   20  O5  UNL     1      -0.779  -2.455  -0.812  1.00  0.00           O  
HETATM   21  C15 UNL     1      -2.440  -2.442   0.917  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.939  -3.684   0.240  1.00  0.00           C  
HETATM   23  C17 UNL     1      -2.168  -2.645   2.373  1.00  0.00           C  
HETATM   24  C18 UNL     1      -3.539  -1.388   0.815  1.00  0.00           C  
HETATM   25  C19 UNL     1       1.830  -0.680   0.324  1.00  0.00           C  
HETATM   26  H1  UNL     1       7.043  -1.547   2.954  1.00  0.00           H  
HETATM   27  H2  UNL     1       5.454  -2.119   2.332  1.00  0.00           H  
HETATM   28  H3  UNL     1       6.979  -2.127   1.286  1.00  0.00           H  
HETATM   29  H4  UNL     1       6.760  -0.026   0.788  1.00  0.00           H  
HETATM   30  H5  UNL     1       4.152  -0.275   2.162  1.00  0.00           H  
HETATM   31  H6  UNL     1       4.678   1.147   1.173  1.00  0.00           H  
HETATM   32  H7  UNL     1       5.002  -0.295  -0.771  1.00  0.00           H  
HETATM   33  H8  UNL     1       3.587  -2.504   0.015  1.00  0.00           H  
HETATM   34  H9  UNL     1       3.609   1.236  -1.784  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.343   1.990  -2.302  1.00  0.00           H  
HETATM   36  H11 UNL     1      -2.156   4.407   0.371  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.609   3.551   0.912  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.747   4.720  -0.498  1.00  0.00           H  
HETATM   39  H14 UNL     1      -4.802   2.413  -1.410  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.167   1.561   0.005  1.00  0.00           H  
HETATM   41  H16 UNL     1      -3.636   1.053  -1.695  1.00  0.00           H  
HETATM   42  H17 UNL     1      -2.745   2.795  -3.163  1.00  0.00           H  
HETATM   43  H18 UNL     1      -3.575   4.276  -2.410  1.00  0.00           H  
HETATM   44  H19 UNL     1      -1.745   4.059  -2.401  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.035  -3.692   0.273  1.00  0.00           H  
HETATM   46  H21 UNL     1      -2.614  -3.664  -0.824  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.549  -4.609   0.727  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.806  -1.673   2.793  1.00  0.00           H  
HETATM   49  H24 UNL     1      -3.162  -2.852   2.869  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.489  -3.480   2.595  1.00  0.00           H  
HETATM   51  H26 UNL     1      -3.072  -0.378   0.886  1.00  0.00           H  
HETATM   52  H27 UNL     1      -4.003  -1.457  -0.184  1.00  0.00           H  
HETATM   53  H28 UNL     1      -4.284  -1.536   1.630  1.00  0.00           H  
HETATM   54  H29 UNL     1       1.963  -1.438   1.070  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29
CONECT    3    4   30   31
CONECT    4    5    6   32
CONECT    5   33
CONECT    6    7    7   25
CONECT    7    8   34
CONECT    8    9    9   35
CONECT    9   10   17
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   15   16
CONECT   14   36   37   38
CONECT   15   39   40   41
CONECT   16   42   43   44
CONECT   17   18   25   25
CONECT   18   19
CONECT   19   20   20   21
CONECT   21   22   23   24
CONECT   22   45   46   47
CONECT   23   48   49   50
CONECT   24   51   52   53
CONECT   25   54
END

HMDB0014592
     RDKit          3D
Dipivefrin
 54 54  0  0  0  0  0  0  0  0999 V2000
    6.3825   -1.5808    2.0382 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1413   -0.2284    1.6305 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7606    0.0558    1.3040 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3250   -0.6634    0.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4327   -2.0280    0.1503 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9595   -0.1853   -0.2912 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7556    0.8026   -1.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4774    1.2271   -1.5504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3619    0.7174   -0.9216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    1.2261   -1.2991 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4756    2.2978   -0.6303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8113    2.7631    0.3314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7699    2.8700   -0.9848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1053    3.9751   -0.0060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8961    1.8737   -1.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7412    3.5455   -2.3617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5504   -0.2472    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -0.7677    0.6653 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2374   -1.8965    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7789   -2.4551   -0.8122 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4401   -2.4424    0.9173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9388   -3.6842    0.2404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1676   -2.6446    2.3732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5392   -1.3876    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303   -0.6803    0.3243 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0432   -1.5473    2.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4544   -2.1187    2.3321 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9785   -2.1273    1.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7600   -0.0256    0.7884 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1525   -0.2745    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6777    1.1474    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0021   -0.2946   -0.7711 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873   -2.5038    0.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6090    1.2355   -1.7835 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3428    1.9896   -2.3018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555    4.4067    0.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6093    3.5513    0.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7465    4.7195   -0.4980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8022    2.4135   -1.4104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1670    1.5615    0.0048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6361    1.0529   -1.6950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7446    2.7953   -3.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5746    4.2763   -2.4095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7450    4.0591   -2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0353   -3.6920    0.2733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6141   -3.6639   -0.8236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5492   -4.6089    0.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8058   -1.6735    2.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1617   -2.8522    2.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4891   -3.4802    2.5952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0720   -0.3777    0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0029   -1.4571   -0.1838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2841   -1.5360    1.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9629   -1.4382    1.0704 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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
  9 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 17 25  2  0
 25  6  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  5 33  1  0
  7 34  1  0
  8 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
 16 43  1  0
 16 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 23 50  1  0
 24 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalate	ChEBI
1-(3',4'-Dipivaloyloxyphenyl)-2-methylamino-1-ethanol	ChEBI
4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalate	ChEBI
Dipivalyl epinephrine	ChEBI
Dipivefrina	ChEBI
Dipivefrine	ChEBI
Dipivefrinum	ChEBI
(+-)-4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalic acid	Generator
4-[1-Hydroxy-2-(methylamino)ethyl]-O-phenylene divavalic acid	Generator
Alcon brand OF dipivefrin hydrochloride	HMDB
Diopine	HMDB
Glaucothil	HMDB
PMS-Dipivefrin	HMDB
Pharm-allergan brand OF dipivefrin hydrochloride	HMDB
Propine	HMDB
Dipivaloylepinephrine	HMDB
Dipivefrin perchlorate	HMDB
Apo-dipivefrin	HMDB
Glaudrops	HMDB
Adrenaline dipivalate	HMDB
Dipivefrin acetate, (+-)-isomer	HMDB
Dipivefrin monophosphate, (+-)-isomer	HMDB
Dipivefrin monosulfate, (+-)-isomer	HMDB
Dipivefrin tartrate (1:1), (+-)-(R-(r,r))-isomer	HMDB
Allergan brand OF dipivefrin hydrochloride	HMDB
Dipoquin	HMDB
Ioquin brand OF dipivefrin hydrochloride	HMDB
Pharmascience brand OF dipivefrin hydrochloride	HMDB
Ratiopharm brand OF dipivefrin hydrochloride	HMDB
D Epifrin	HMDB
Dipivefrin citrate (1:1), (+-)-isomer	HMDB
Dipivefrin nitrate, (+-)-isomer	HMDB
Dipivefrin propanoate, (+-)-isomer	HMDB
Dipivefrin tartrate (1:1), (R)-(R-(r,r))-isomer	HMDB
Apotex brand OF dipivefrin hydrochloride	HMDB
Dipivefrin hydrochloride	HMDB
Dipivefrin hydrochloride, (+-)-isomer	HMDB
Dipivefrin, (R)-isomer	HMDB
Ratio-dipivefrin	HMDB

Chemical Formula

C₁₉H₂₉NO₅

Average Molecular Weight

351.4373

Monoisotopic Molecular Weight

351.204573043

IUPAC Name

2-[(2,2-dimethylpropanoyl)oxy]-5-[1-hydroxy-2-(methylamino)ethyl]phenyl 2,2-dimethylpropanoate

Traditional Name

dipivefrin

CAS Registry Number

52365-63-6

SMILES

CNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C1

InChI Identifier

InChI=1S/C19H29NO5/c1-18(2,3)16(22)24-14-9-8-12(13(21)11-20-7)10-15(14)25-17(23)19(4,5)6/h8-10,13,20-21H,11H2,1-7H3

InChI Key

OCUJLLGVOUDECM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Aralkylamine
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
1,2-aminoalcohol
Amino acid or derivatives
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Secondary aliphatic amine
Secondary amine
Organic nitrogen compound
Organonitrogen compound
Organooxygen compound
Aromatic alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Amine
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

ethanolamines (CHEBI:4646 )
pivalate ester (CHEBI:4646 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014592)
Membrane (HMDB: HMDB0014592)

Source

Exogenous

Exogenous (HMDB: HMDB0014592)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.058 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	3.17	ALOGPS
logP	3.71	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	14	ChemAxon
pKa (Strongest Basic)	9.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	84.86 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	94.94 m³·mol⁻¹	ChemAxon
Polarizability	38.65 Å³	ChemAxon
Number of Rings	1	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]+	183.509	31661259
DarkChem	[M-H]-	183.594	31661259
DeepCCS	[M+H]+	191.364	30932474
DeepCCS	[M-H]-	188.78	30932474
DeepCCS	[M-2H]-	223.316	30932474
DeepCCS	[M+Na]+	198.852	30932474
AllCCS	[M+H]+	183.2	32859911
AllCCS	[M+H-H2O]+	180.7	32859911
AllCCS	[M+NH4]+	185.6	32859911
AllCCS	[M+Na]+	186.3	32859911
AllCCS	[M-H]-	191.8	32859911
AllCCS	[M+Na-2H]-	192.3	32859911
AllCCS	[M+HCOO]-	193.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.81 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2914 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.85 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1870.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	199.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	73.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	447.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	469.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	917.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	431.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1448.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	290.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	326.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	224.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dipivefrin	CNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C1	2357.6	Standard polar	33892256
Dipivefrin	CNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C1	2223.8	Standard non polar	33892256
Dipivefrin	CNCC(O)C1=CC(OC(=O)C(C)(C)C)=C(OC(=O)C(C)(C)C)C=C1	2219.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dipivefrin,1TMS,isomer #1	CNCC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1	2150.6	Semi standard non polar	33892256
Dipivefrin,1TMS,isomer #2	CN(CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C	2318.0	Semi standard non polar	33892256
Dipivefrin,2TMS,isomer #1	CN(CC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C	2294.9	Semi standard non polar	33892256
Dipivefrin,2TMS,isomer #1	CN(CC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C	2426.3	Standard non polar	33892256
Dipivefrin,2TMS,isomer #1	CN(CC(O[Si](C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C	2573.9	Standard polar	33892256
Dipivefrin,1TBDMS,isomer #1	CNCC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1	2368.3	Semi standard non polar	33892256
Dipivefrin,1TBDMS,isomer #2	CN(CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2573.1	Semi standard non polar	33892256
Dipivefrin,2TBDMS,isomer #1	CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2784.2	Semi standard non polar	33892256
Dipivefrin,2TBDMS,isomer #1	CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2808.8	Standard non polar	33892256
Dipivefrin,2TBDMS,isomer #1	CN(CC(O[Si](C)(C)C(C)(C)C)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2808.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dipivefrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9150000000-30a32fb00720193ce912	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dipivefrin GC-MS (1 TMS) - 70eV, Positive	splash10-0a4l-9044000000-b32f8d364631e20e4017	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dipivefrin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 10V, Positive-QTOF	splash10-0f89-0049000000-cef336a5e244ea16b9f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 20V, Positive-QTOF	splash10-0kai-4059000000-c483238390ca6a1eaa68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 40V, Positive-QTOF	splash10-0a59-9351000000-607bb994262a9b103492	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 10V, Negative-QTOF	splash10-0udi-0109000000-2ce96b91437661fde684	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 20V, Negative-QTOF	splash10-0ue9-2449000000-59429e2be741d17c8117	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 40V, Negative-QTOF	splash10-0udi-3910000000-eb3054746367b77b8eed	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 10V, Positive-QTOF	splash10-0ue9-0019000000-4099393ff81d85a0ef03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 20V, Positive-QTOF	splash10-0f89-0059000000-459602b5970b064ff34c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 40V, Positive-QTOF	splash10-0a4i-9383000000-22ec9c056edfb61e9b13	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 10V, Negative-QTOF	splash10-0udi-0019000000-6628a7bbb51fbe187be7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 20V, Negative-QTOF	splash10-0udi-0759000000-ec60a4f35ccc46b4a95a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dipivefrin 40V, Negative-QTOF	splash10-0f79-6692000000-669ea5989d4d3ee82487	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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 DB00449	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00449	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00449

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2994

KEGG Compound ID

C06963

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dipivefrin

METLIN ID

Not Available

PubChem Compound

3105

PDB ID

Not Available

ChEBI ID

4646

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. Cholinesterase

General function:: Involved in carboxylesterase activity
Specific function:: Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
Gene Name:: BCHE
Uniprot ID:: P06276
Molecular weight:: 68417.575

References

Nakamura M, Shirasawa E, Hikida M: Characterization of esterases involved in the hydrolysis of dipivefrin hydrochloride. Ophthalmic Res. 1993;25(1):46-51. [PubMed:8446367 ]

Enzyme Details

2. 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

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
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. [PubMed:17016423 ]

Enzyme Details

3. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Ozakca I, Arioglu E, Guner S, Altan VM, Ozcelikay AT: Role of beta-3-adrenoceptor in catecholamine-induced relaxations in gastric fundus from control and diabetic rats. Pharmacology. 2007;80(4):227-38. Epub 2007 Jul 6. [PubMed:17622774 ]
Prenner L, Sieben A, Zeller K, Weiser D, Haberlein H: Reduction of high-affinity beta2-adrenergic receptor binding by hyperforin and hyperoside on rat C6 glioblastoma cells measured by fluorescence correlation spectroscopy. Biochemistry. 2007 May 1;46(17):5106-13. Epub 2007 Apr 7. [PubMed:17417877 ]
Lucin KM, Sanders VM, Jones TB, Malarkey WB, Popovich PG: Impaired antibody synthesis after spinal cord injury is level dependent and is due to sympathetic nervous system dysregulation. Exp Neurol. 2007 Sep;207(1):75-84. Epub 2007 Jun 2. [PubMed:17597612 ]

Enzyme Details

4. 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

Sanbe A, Tanaka Y, Fujiwara Y, Tsumura H, Yamauchi J, Cotecchia S, Koike K, Tsujimoto G, Tanoue A: Alpha1-adrenoceptors are required for normal male sexual function. Br J Pharmacol. 2007 Oct;152(3):332-40. Epub 2007 Jul 2. [PubMed:17603545 ]
Tomiyama Y, Kobayashi K, Tadachi M, Kobayashi S, Inada Y, Kobayashi M, Yamazaki Y: Expressions and mechanical functions of alpha1-adrenoceptor subtypes in hamster ureter. Eur J Pharmacol. 2007 Nov 14;573(1-3):201-5. Epub 2007 Jul 6. [PubMed:17658513 ]

Showing metabocard for Dipivefrin (HMDB0014592)

MOL for HMDB0014592 (Dipivefrin)

3D MOL for HMDB0014592 (Dipivefrin)

3D SDF for HMDB0014592 (Dipivefrin)

3D-SDF for HMDB0014592 (Dipivefrin)

PDB for HMDB0014592 (Dipivefrin)

3D PDB for HMDB0014592 (Dipivefrin)

SMILES for HMDB0014592 (Dipivefrin)

INCHI for HMDB0014592 (Dipivefrin)

Structure for HMDB0014592 (Dipivefrin)

3D Structure for HMDB0014592 (Dipivefrin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References