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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014443

Secondary Accession Numbers

HMDB14443

Metabolite Identification

Common Name

Dapiprazole

Description

Dapiprazole is only found in individuals that have used or taken this drug. It is an alpha blocker. It is used to reverse mydriasis after eye examination. [Wikipedia ]Dapiprazole acts through blocking the alpha1-adrenergic receptors in smooth muscle. It produces miosis through an effect on the dilator muscle of the iris and does not have any significant activity on ciliary muscle contraction and, therefore does not induce a significant change in the anterior chamber depth or the thickness of the lens.

Structure

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

HMDB0014443
     RDKit          3D
Dapiprazole
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.0905   -1.1412   -1.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9033   -0.6196   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3011   -0.7193   -0.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0804   -0.2372    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5074    0.3683    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    0.4676    1.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -0.0189    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    0.1033    0.5126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -1.0379    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -0.6198    0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    0.3781   -0.4830 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    0.5615   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    1.1142    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1915    1.2717   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    2.3414   -0.9905 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9468    2.0743   -1.3519 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037    0.8109   -0.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1077    0.3101   -0.3699 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -1.0459    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619   -1.2062    0.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -0.7487    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3735   -0.1030   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802    1.5270   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045    1.4263    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -0.5926   -1.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309   -2.2519   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6887   -1.0179   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7259   -1.1975   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1763   -0.3249    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1249    0.7510    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6559    0.9421    2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212   -1.5046    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933   -1.8096   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0184   -1.5186    0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -0.2753    1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0044    1.2756   -1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.3731   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334    2.1038    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    0.3961    0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2462   -1.2138    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -1.7955   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2204   -0.6280    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4143   -2.3118    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -0.0066    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376   -1.5904    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525    0.4814   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1288   -0.8360   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5637    1.7848   -1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5544    2.4183   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100    1.6615    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809    2.1769    0.2719 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  1  0
  7  2  1  0
 24  8  1  0
 18 14  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 19 40  1  0
 19 41  1  0
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 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
M  END

298
  Mrv0541 02231214352D          

 24 27  0  0  0  0            999 V2000
    5.1795   -0.3468    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6921    1.2216    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -2.3367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411   -2.7492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -3.4131    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9868   -0.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6285    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9232   -1.1309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2431    0.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8848    1.0515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1159   -1.3010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -2.0853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -2.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -3.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -3.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -3.1617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484    2.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7557    2.1760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3974    2.6199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0120    2.9601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3066    1.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6537    3.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4610    3.5742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 18  1  0  0  0  0
  3 12  1  0  0  0  0
  3 13  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  2  0  0  0  0
  5 17  2  0  0  0  0
  6  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 19 21  2  0  0  0  0
 19 22  1  0  0  0  0
 20 23  1  0  0  0  0
 21 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014443

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=CC=C1N1CCN(CCC2=NN=C3CCCCN23)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C19H27N5/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19/h2-3,6-7H,4-5,8-15H2,1H3

> <INCHI_KEY>
RFWZESUMWJKKRN-UHFFFAOYSA-N

> <FORMULA>
C19H27N5

> <MOLECULAR_WEIGHT>
325.4512

> <EXACT_MASS>
325.226645889

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.22537003271229

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2-methylphenyl)-4-(2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine

> <ALOGPS_LOGP>
2.78

> <JCHEM_LOGP>
2.415873690666666

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.667908152684471

> <JCHEM_POLAR_SURFACE_AREA>
37.19

> <JCHEM_REFRACTIVITY>
100.22160000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dapiprazole

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0014443
     RDKit          3D
Dapiprazole
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.0905   -1.1412   -1.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9033   -0.6196   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3011   -0.7193   -0.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0804   -0.2372    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5074    0.3683    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    0.4676    1.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -0.0189    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    0.1033    0.5126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -1.0379    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -0.6198    0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    0.3781   -0.4830 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    0.5615   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    1.1142    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1915    1.2717   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    2.3414   -0.9905 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9468    2.0743   -1.3519 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037    0.8109   -0.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1077    0.3101   -0.3699 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -1.0459    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619   -1.2062    0.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -0.7487    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3735   -0.1030   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802    1.5270   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045    1.4263    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -0.5926   -1.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309   -2.2519   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6887   -1.0179   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7259   -1.1975   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1763   -0.3249    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1249    0.7510    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6559    0.9421    2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212   -1.5046    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933   -1.8096   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0184   -1.5186    0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -0.2753    1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0044    1.2756   -1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.3731   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334    2.1038    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    0.3961    0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2462   -1.2138    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -1.7955   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2204   -0.6280    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4143   -2.3118    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -0.0066    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376   -1.5904    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525    0.4814   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1288   -0.8360   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5637    1.7848   -1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5544    2.4183   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100    1.6615    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809    2.1769    0.2719 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  1  0
  7  2  1  0
 24  8  1  0
 18 14  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 298                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       9.668  -0.647   0.000  0.00  0.00           N+0
HETATM    2  N   UNK     0      10.625   2.280   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       5.747  -4.362   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       8.103  -5.132   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.205  -6.371   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      11.175  -0.330   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.640   0.499   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.190  -2.111   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      11.654   1.134   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.118   1.963   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.683  -2.429   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.592   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.205  -3.893   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080  -4.362   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -5.902   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414  -6.672   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.747  -5.902   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.104   3.744   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.611   4.062   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.075   4.890   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.089   5.526   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.639   2.916   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.554   6.354   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.061   6.672   0.000  0.00  0.00           C+0
CONECT    1    6    7    8                                                  
CONECT    2    9   10   18                                                  
CONECT    3   12   13   17                                                  
CONECT    4    5   13                                                       
CONECT    5    4   17                                                       
CONECT    6    1    9                                                       
CONECT    7    1   10                                                       
CONECT    8    1   11                                                       
CONECT    9    2    6                                                       
CONECT   10    2    7                                                       
CONECT   11    8   13                                                       
CONECT   12    3   14                                                       
CONECT   13    3    4   11                                                  
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17    3    5   16                                                  
CONECT   18    2   19   20                                                  
CONECT   19   18   21   22                                                  
CONECT   20   18   23                                                       
CONECT   21   19   24                                                       
CONECT   22   19                                                            
CONECT   23   20   24                                                       
CONECT   24   21   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0014443
HETATM    1  C1  UNL     1      -4.091  -1.141  -1.797  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.903  -0.620  -0.669  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.301  -0.719  -0.689  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.080  -0.237   0.338  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.507   0.368   1.436  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.134   0.468   1.459  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.327  -0.019   0.420  1.00  0.00           C  
HETATM    8  N1  UNL     1      -2.905   0.103   0.513  1.00  0.00           N  
HETATM    9  C8  UNL     1      -2.034  -1.038   0.605  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.585  -0.620   0.491  1.00  0.00           C  
HETATM   11  N2  UNL     1      -0.359   0.378  -0.483  1.00  0.00           N  
HETATM   12  C10 UNL     1       0.961   0.561  -0.955  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.821   1.114   0.165  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.192   1.272  -0.397  1.00  0.00           C  
HETATM   15  N3  UNL     1       3.693   2.341  -0.991  1.00  0.00           N  
HETATM   16  N4  UNL     1       4.947   2.074  -1.352  1.00  0.00           N  
HETATM   17  C13 UNL     1       5.204   0.811  -0.966  1.00  0.00           C  
HETATM   18  N5  UNL     1       4.108   0.310  -0.370  1.00  0.00           N  
HETATM   19  C14 UNL     1       4.102  -1.046   0.144  1.00  0.00           C  
HETATM   20  C15 UNL     1       5.362  -1.206   0.963  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.603  -0.749   0.273  1.00  0.00           C  
HETATM   22  C17 UNL     1       6.373  -0.103  -1.052  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.180   1.527  -0.474  1.00  0.00           C  
HETATM   24  C19 UNL     1      -2.304   1.426   0.518  1.00  0.00           C  
HETATM   25  H1  UNL     1      -3.166  -0.593  -1.972  1.00  0.00           H  
HETATM   26  H2  UNL     1      -3.931  -2.252  -1.727  1.00  0.00           H  
HETATM   27  H3  UNL     1      -4.689  -1.018  -2.751  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.726  -1.197  -1.562  1.00  0.00           H  
HETATM   29  H5  UNL     1      -8.176  -0.325   0.305  1.00  0.00           H  
HETATM   30  H6  UNL     1      -7.125   0.751   2.250  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.656   0.942   2.317  1.00  0.00           H  
HETATM   32  H8  UNL     1      -2.121  -1.505   1.633  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.193  -1.810  -0.167  1.00  0.00           H  
HETATM   34  H10 UNL     1       0.018  -1.519   0.238  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.229  -0.275   1.488  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.004   1.276  -1.829  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.455  -0.373  -1.294  1.00  0.00           H  
HETATM   38  H14 UNL     1       1.433   2.104   0.506  1.00  0.00           H  
HETATM   39  H15 UNL     1       1.791   0.396   0.992  1.00  0.00           H  
HETATM   40  H16 UNL     1       3.246  -1.214   0.832  1.00  0.00           H  
HETATM   41  H17 UNL     1       4.020  -1.796  -0.672  1.00  0.00           H  
HETATM   42  H18 UNL     1       5.220  -0.628   1.902  1.00  0.00           H  
HETATM   43  H19 UNL     1       5.414  -2.312   1.200  1.00  0.00           H  
HETATM   44  H20 UNL     1       7.143  -0.007   0.917  1.00  0.00           H  
HETATM   45  H21 UNL     1       7.338  -1.590   0.128  1.00  0.00           H  
HETATM   46  H22 UNL     1       7.252   0.481  -1.391  1.00  0.00           H  
HETATM   47  H23 UNL     1       6.129  -0.836  -1.857  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.564   1.785  -1.485  1.00  0.00           H  
HETATM   49  H25 UNL     1      -0.554   2.418  -0.168  1.00  0.00           H  
HETATM   50  H26 UNL     1      -1.910   1.662   1.533  1.00  0.00           H  
HETATM   51  H27 UNL     1      -3.081   2.177   0.272  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    3    7
CONECT    3    4   28
CONECT    4    5    5   29
CONECT    5    6   30
CONECT    6    7    7   31
CONECT    7    8
CONECT    8    9   24
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   23
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   15   18
CONECT   15   16
CONECT   16   17   17
CONECT   17   18   22
CONECT   18   19
CONECT   19   20   40   41
CONECT   20   21   42   43
CONECT   21   22   44   45
CONECT   22   46   47
CONECT   23   24   48   49
CONECT   24   50   51
END

HMDB0014443
     RDKit          3D
Dapiprazole
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.0905   -1.1412   -1.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9033   -0.6196   -0.6694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3011   -0.7193   -0.6895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0804   -0.2372    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5074    0.3683    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1337    0.4676    1.4585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3267   -0.0189    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9046    0.1033    0.5126 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0341   -1.0379    0.6054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853   -0.6198    0.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3588    0.3781   -0.4830 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9610    0.5615   -0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8214    1.1142    0.1650 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1915    1.2717   -0.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6934    2.3414   -0.9905 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9468    2.0743   -1.3519 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037    0.8109   -0.9656 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1077    0.3101   -0.3699 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1019   -1.0459    0.1439 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3619   -1.2062    0.9626 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6032   -0.7487    0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3735   -0.1030   -1.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1802    1.5270   -0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3045    1.4263    0.5178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1659   -0.5926   -1.9717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9309   -2.2519   -1.7266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6887   -1.0179   -2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7259   -1.1975   -1.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1763   -0.3249    0.3048 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1249    0.7510    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6559    0.9421    2.3174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1212   -1.5046    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1933   -1.8096   -0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0184   -1.5186    0.2383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2295   -0.2753    1.4883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0044    1.2756   -1.8285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4554   -0.3731   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4334    2.1038    0.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7912    0.3961    0.9917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2462   -1.2138    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0198   -1.7955   -0.6722 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2204   -0.6280    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4143   -2.3118    1.2001 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1434   -0.0066    0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3376   -1.5904    0.1284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2525    0.4814   -1.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1288   -0.8360   -1.8573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5637    1.7848   -1.4849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5544    2.4183   -0.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9100    1.6615    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809    2.1769    0.2719 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  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 11 23  1  0
 23 24  1  0
  7  2  1  0
 24  8  1  0
 18 14  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  6 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 19 40  1  0
 19 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
 22 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
 24 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6,7,8-Tetrahydro-3-(2-(4-(O-tolyl)-1-piperazinyl)ethyl)-S-triazolo(4,3-a)pyridine	ChEBI
Dapiprazol	ChEBI
Dapiprazolum	ChEBI
Rev-eyes	HMDB
Remydrial	HMDB
Dapiprazole hydrochloride	HMDB
3-(2-(4-(2-Methylphenyl)-1-piperazinyl)ethyl)-5,6,7,8,-tetrahydro-1,2,4-triazolo(4,3-a)pyridine hydrochloride	HMDB

Chemical Formula

C₁₉H₂₇N₅

Average Molecular Weight

325.4512

Monoisotopic Molecular Weight

325.226645889

IUPAC Name

1-(2-methylphenyl)-4-(2-{5H,6H,7H,8H-[1,2,4]triazolo[4,3-a]pyridin-3-yl}ethyl)piperazine

Traditional Name

dapiprazole

CAS Registry Number

72822-12-9

SMILES

CC1=CC=CC=C1N1CCN(CCC2=NN=C3CCCCN23)CC1

InChI Identifier

InChI=1S/C19H27N5/c1-16-6-2-3-7-17(16)23-14-12-22(13-15-23)11-9-19-21-20-18-8-4-5-10-24(18)19/h2-3,6-7H,4-5,8-15H2,1H3

InChI Key

RFWZESUMWJKKRN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpiperazines. Phenylpiperazines are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazinanes

Sub Class

Piperazines

Direct Parent

Phenylpiperazines

Alternative Parents

Substituents

Phenylpiperazine
N-arylpiperazine
Triazolopyridine
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aniline or substituted anilines
Aminotoluene
Aralkylamine
N-alkylpiperazine
Toluene
Benzenoid
Monocyclic benzene moiety
Pyridine
Heteroaromatic compound
1,2,4-triazole
Triazole
Azole
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organonitrogen compound
Amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

N-arylpiperazine (CHEBI:51066 )
pyridines (CHEBI:51066 )
N-alkylpiperazine (CHEBI:51066 )

Ontology

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	0.75 g/L	Not Available
LogP	2.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.75 g/L	ALOGPS
logP	2.78	ALOGPS
logP	2.42	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	7.67	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	37.19 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	100.22 m³·mol⁻¹	ChemAxon
Polarizability	38.23 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.313	31661259
DarkChem	[M-H]-	177.984	31661259
DeepCCS	[M-2H]-	206.885	30932474
DeepCCS	[M+Na]+	182.45	30932474
AllCCS	[M+H]+	181.5	32859911
AllCCS	[M+H-H2O]+	178.6	32859911
AllCCS	[M+NH4]+	184.3	32859911
AllCCS	[M+Na]+	185.0	32859911
AllCCS	[M-H]-	182.0	32859911
AllCCS	[M+Na-2H]-	182.0	32859911
AllCCS	[M+HCOO]-	182.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dapiprazole	CC1=CC=CC=C1N1CCN(CCC2=NN=C3CCCCN23)CC1	3741.0	Standard polar	33892256
Dapiprazole	CC1=CC=CC=C1N1CCN(CCC2=NN=C3CCCCN23)CC1	2908.4	Standard non polar	33892256
Dapiprazole	CC1=CC=CC=C1N1CCN(CCC2=NN=C3CCCCN23)CC1	3136.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dapiprazole GC-MS (Non-derivatized) - 70eV, Positive	splash10-002s-3910000000-c735602ffc4fd3bbf5c0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dapiprazole GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dapiprazole 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 - Dapiprazole 10V, Positive-QTOF	splash10-004i-0109000000-7cf219c3382f77e31dd9	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 20V, Positive-QTOF	splash10-0f96-5924000000-c97098cf997e5a450a37	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 40V, Positive-QTOF	splash10-0kml-5910000000-1e34f26f6ea9c6248f9b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 10V, Negative-QTOF	splash10-00di-0109000000-1635977d96b0138334f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 20V, Negative-QTOF	splash10-00fr-0829000000-03c184bf1a634bc97883	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 40V, Negative-QTOF	splash10-057l-6900000000-def5e7db9d9837fcdca3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 10V, Positive-QTOF	splash10-004i-0009000000-d29345d75948c8e1f1f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 20V, Positive-QTOF	splash10-004i-0109000000-b3a194584f3a032aaf20	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 40V, Positive-QTOF	splash10-0udj-4940000000-651af9305d00e98f3786	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 10V, Negative-QTOF	splash10-00di-0009000000-554b0601f41d562d92cb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 20V, Negative-QTOF	splash10-00di-0029000000-52a289ee18a4243572e2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dapiprazole 40V, Negative-QTOF	splash10-00di-1921000000-32b24dfdde20de8deb85	2021-09-22	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 DB00298	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00298	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00298

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2298190

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dapiprazole

METLIN ID

Not Available

PubChem Compound

3033538

PDB ID

Not Available

ChEBI ID

51066

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-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

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 ]
Eltze M: Affinity of the miotic drug, dapiprazole, at alpha 1-adrenoceptor subtypes A, B and D. J Pharm Pharmacol. 1997 Nov;49(11):1091-5. [PubMed:9401944 ]

Enzyme Details

2. Alpha-1B 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
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

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. Alpha-1D adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium
Gene Name:: ADRA1D
Uniprot ID:: P25100
Molecular weight:: 60462.2

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 ]

Showing metabocard for Dapiprazole (HMDB0014443)

MOL for HMDB0014443 (Dapiprazole)

3D MOL for HMDB0014443 (Dapiprazole)

3D SDF for HMDB0014443 (Dapiprazole)

3D-SDF for HMDB0014443 (Dapiprazole)

PDB for HMDB0014443 (Dapiprazole)

3D PDB for HMDB0014443 (Dapiprazole)

SMILES for HMDB0014443 (Dapiprazole)

INCHI for HMDB0014443 (Dapiprazole)

Structure for HMDB0014443 (Dapiprazole)

3D Structure for HMDB0014443 (Dapiprazole)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References