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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014958

Secondary Accession Numbers

HMDB14958

Metabolite Identification

Common Name

Tadalafil

Description

Tadalafil is an orally adminstered drug used to treat male erectile dysfunction (impotence). It is marketed worldwide under the brand name Cialis. It is a phosphodiesterase 5 (PDE5) inhibitor. Tadalafil's distinguishing pharmacologic feature is its longer half-life (17.5 hours) compared with Viagra and Levitra (4-5 hours). This longer half-life results in a longer duration of action and is, in part, responsible for the Cialis nickname of the 'weekend pill.' This longer half-life also is the basis of current investigation for tadalafil's use in pulmonary arterial hypertension as a once-daily therapy. [Wikipedia ]

Structure

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

820
  Mrv0541 02231215012D          

 30 35  0  0  1  0            999 V2000
    7.2908    0.5262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3835    2.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999    2.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159    0.9412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5878    1.8063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8304    0.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4015    0.5287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8304   -0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159   -0.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5811    0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1027    1.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6870    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    2.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276   -1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4555   -2.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6870    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675   -2.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3038    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725    2.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134   -2.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842    3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3994    0.1944    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2 15  2  0  0  0  0
  3 24  1  0  0  0  0
  3 29  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 15  1  0  0  0  0
  6 11  1  0  0  0  0
  6 18  1  0  0  0  0
  7 13  1  0  0  0  0
  7 17  1  0  0  0  0
  7 23  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  8 30  1  6  0  0  0
  9 11  1  0  0  0  0
  9 16  1  1  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
 12 14  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 17  1  0  0  0  0
 16 20  2  0  0  0  0
 16 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 25  1  0  0  0  0
 20 24  1  0  0  0  0
 21 26  2  0  0  0  0
 22 27  1  0  0  0  0
 24 28  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END

HMDB0014958
     RDKit          3D
Tadalafil
 48 53  0  0  0  0  0  0  0  0999 V2000
   -3.4756   -4.2554    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -3.2600   -0.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938   -3.6763   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -2.5519   -1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232   -2.7340   -2.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -1.2461   -0.9766 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069   -0.8356   -0.1752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4570    0.2047    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627    1.3401    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736    1.0695   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662    2.1744   -1.6627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870    3.1998   -1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    4.5404   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    5.4481   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8871    4.9287    0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8976    3.5814    0.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    2.6909   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -0.3649   -1.2307 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5070   -0.6144   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -1.8786   -0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -2.0525    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8320   -0.9701    1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    0.2885    0.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    0.4575    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157    1.2201    1.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183    0.5246    1.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9607   -0.8454    1.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.9345    0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844   -1.7024    1.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4199   -5.0674   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4975   -3.7924    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2806   -4.6210    1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081   -4.5644   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -3.9813    0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -0.2708   -0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -0.2091    1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2557    0.5009    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    2.2663   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    4.9153   -2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    6.5182   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    5.6052    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    3.1539    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -0.5290   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051   -2.6931   -0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626   -3.0408    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091    1.4901    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1049    0.7687    1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    0.8043    2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  2  0
 28  2  1  0
 18  6  1  0
 24 19  1  0
 17  9  1  0
 27 22  1  0
 17 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  7 35  1  6
  8 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  6
 20 44  1  0
 21 45  1  0
 24 46  1  0
 26 47  1  0
 26 48  1  0
M  END

820
  Mrv0541 02231215012D          

 30 35  0  0  1  0            999 V2000
    7.2908    0.5262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3835    2.2047    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7999    2.9805    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.3166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159    0.9412    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7934   -0.8466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5878    1.8063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8304    0.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4015    0.5287    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.8304   -0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4015   -0.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1159   -0.7088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5811    0.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9433   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1027    1.8005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6870    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8436    2.2359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1276   -1.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4555   -2.1943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6870    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725    0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7675   -2.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3038    2.2160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9725    2.1787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1134   -2.9770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    0.9412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2637   -3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2580    1.7662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9842    3.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3994    0.1944    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  2  0  0  0  0
  2 15  2  0  0  0  0
  3 24  1  0  0  0  0
  3 29  1  0  0  0  0
  4 28  1  0  0  0  0
  4 29  1  0  0  0  0
  5  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 15  1  0  0  0  0
  6 11  1  0  0  0  0
  6 18  1  0  0  0  0
  7 13  1  0  0  0  0
  7 17  1  0  0  0  0
  7 23  1  0  0  0  0
  8 10  1  0  0  0  0
  8 13  1  0  0  0  0
  8 30  1  6  0  0  0
  9 11  1  0  0  0  0
  9 16  1  1  0  0  0
 10 12  1  0  0  0  0
 11 12  2  0  0  0  0
 12 14  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  2  0  0  0  0
 15 17  1  0  0  0  0
 16 20  2  0  0  0  0
 16 21  1  0  0  0  0
 18 22  2  0  0  0  0
 19 25  1  0  0  0  0
 20 24  1  0  0  0  0
 21 26  2  0  0  0  0
 22 27  1  0  0  0  0
 24 28  2  0  0  0  0
 25 27  2  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014958

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1

> <INCHI_KEY>
WOXKDUGGOYFFRN-IIBYNOLFSA-N

> <FORMULA>
C22H19N3O4

> <MOLECULAR_WEIGHT>
389.404

> <EXACT_MASS>
389.137556111

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.921935442019524

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),11,13,15-tetraene-4,7-dione

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
1.6393403350000002

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.73994401241041

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.169919973818779

> <JCHEM_PKA_STRONGEST_BASIC>
-4.233477677173523

> <JCHEM_POLAR_SURFACE_AREA>
74.87

> <JCHEM_REFRACTIVITY>
104.08160000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tadalafil

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014958
     RDKit          3D
Tadalafil
 48 53  0  0  0  0  0  0  0  0999 V2000
   -3.4756   -4.2554    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -3.2600   -0.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938   -3.6763   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -2.5519   -1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232   -2.7340   -2.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -1.2461   -0.9766 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069   -0.8356   -0.1752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4570    0.2047    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627    1.3401    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736    1.0695   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662    2.1744   -1.6627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870    3.1998   -1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    4.5404   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    5.4481   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8871    4.9287    0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8976    3.5814    0.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    2.6909   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -0.3649   -1.2307 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5070   -0.6144   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -1.8786   -0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -2.0525    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8320   -0.9701    1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    0.2885    0.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    0.4575    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157    1.2201    1.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183    0.5246    1.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9607   -0.8454    1.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.9345    0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844   -1.7024    1.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4199   -5.0674   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4975   -3.7924    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2806   -4.6210    1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081   -4.5644   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -3.9813    0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -0.2708   -0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -0.2091    1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2557    0.5009    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    2.2663   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    4.9153   -2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    6.5182   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    5.6052    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    3.1539    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -0.5290   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051   -2.6931   -0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626   -3.0408    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091    1.4901    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1049    0.7687    1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    0.8043    2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  2  0
 28  2  1  0
 18  6  1  0
 24 19  1  0
 17  9  1  0
 27 22  1  0
 17 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  7 35  1  6
  8 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  6
 20 44  1  0
 21 45  1  0
 24 46  1  0
 26 47  1  0
 26 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 820                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      13.609   0.982   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.183   4.115   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.226   5.564   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   4.324   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.550   1.757   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       7.081  -1.580   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      12.297   3.372   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      10.883   0.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.216   0.987   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.883  -0.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.216  -0.553   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.550  -1.323   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.285   1.768   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.227  -2.820   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.525   3.361   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.882   1.757   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.908   4.174   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.705  -2.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.184  -4.096   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.882   3.297   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.549   0.987   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.033  -4.424   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      13.634   4.137   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.549   4.067   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.545  -5.557   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.215   1.757   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.959  -5.722   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.215   3.297   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.704   5.722   0.000  0.00  0.00           C+0
HETATM   30  H   UNK     0      11.946   0.363   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   15                                                            
CONECT    3   24   29                                                       
CONECT    4   28   29                                                       
CONECT    5    8    9   15                                                  
CONECT    6   11   18                                                       
CONECT    7   13   17   23                                                  
CONECT    8    5   10   13   30                                             
CONECT    9    5   11   16                                                  
CONECT   10    8   12                                                       
CONECT   11    6    9   12                                                  
CONECT   12   10   11   14                                                  
CONECT   13    1    7    8                                                  
CONECT   14   12   18   19                                                  
CONECT   15    2    5   17                                                  
CONECT   16    9   20   21                                                  
CONECT   17    7   15                                                       
CONECT   18    6   14   22                                                  
CONECT   19   14   25                                                       
CONECT   20   16   24                                                       
CONECT   21   16   26                                                       
CONECT   22   18   27                                                       
CONECT   23    7                                                            
CONECT   24    3   20   28                                                  
CONECT   25   19   27                                                       
CONECT   26   21   28                                                       
CONECT   27   22   25                                                       
CONECT   28    4   24   26                                                  
CONECT   29    3    4                                                       
CONECT   30    8                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

COMPND    HMDB0014958
HETATM    1  C1  UNL     1      -3.476  -4.255   0.290  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.460  -3.260  -0.010  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.294  -3.676  -0.740  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.777  -2.552  -1.547  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.323  -2.734  -2.733  1.00  0.00           O  
HETATM    6  N2  UNL     1      -0.791  -1.246  -0.977  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.907  -0.836  -0.175  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.457   0.205   0.817  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.963   1.340   0.011  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.074   1.069  -1.039  1.00  0.00           C  
HETATM   11  N3  UNL     1       0.266   2.174  -1.663  1.00  0.00           N  
HETATM   12  C8  UNL     1      -0.387   3.200  -1.043  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.390   4.540  -1.286  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.127   5.448  -0.541  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.887   4.929   0.495  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.898   3.581   0.756  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.147   2.691  -0.009  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.307  -0.365  -1.231  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.507  -0.614  -0.437  1.00  0.00           C  
HETATM   20  C16 UNL     1       2.022  -1.879  -0.236  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.173  -2.052   0.532  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.832  -0.970   1.113  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.313   0.289   0.908  1.00  0.00           C  
HETATM   24  C20 UNL     1       2.169   0.458   0.145  1.00  0.00           C  
HETATM   25  O2  UNL     1       4.116   1.220   1.570  1.00  0.00           O  
HETATM   26  C21 UNL     1       5.318   0.525   1.899  1.00  0.00           C  
HETATM   27  O3  UNL     1       4.961  -0.845   1.901  1.00  0.00           O  
HETATM   28  C22 UNL     1      -2.658  -1.935   0.426  1.00  0.00           C  
HETATM   29  O4  UNL     1      -3.484  -1.702   1.335  1.00  0.00           O  
HETATM   30  H1  UNL     1      -3.420  -5.067  -0.474  1.00  0.00           H  
HETATM   31  H2  UNL     1      -4.497  -3.792   0.220  1.00  0.00           H  
HETATM   32  H3  UNL     1      -3.281  -4.621   1.314  1.00  0.00           H  
HETATM   33  H4  UNL     1      -1.508  -4.564  -1.384  1.00  0.00           H  
HETATM   34  H5  UNL     1      -0.533  -3.981   0.038  1.00  0.00           H  
HETATM   35  H6  UNL     1      -2.585  -0.271  -0.891  1.00  0.00           H  
HETATM   36  H7  UNL     1      -0.629  -0.209   1.466  1.00  0.00           H  
HETATM   37  H8  UNL     1      -2.256   0.501   1.518  1.00  0.00           H  
HETATM   38  H9  UNL     1       0.911   2.266  -2.478  1.00  0.00           H  
HETATM   39  H10 UNL     1       0.213   4.915  -2.101  1.00  0.00           H  
HETATM   40  H11 UNL     1      -1.105   6.518  -0.764  1.00  0.00           H  
HETATM   41  H12 UNL     1      -2.474   5.605   1.097  1.00  0.00           H  
HETATM   42  H13 UNL     1      -2.486   3.154   1.562  1.00  0.00           H  
HETATM   43  H14 UNL     1       0.595  -0.529  -2.314  1.00  0.00           H  
HETATM   44  H15 UNL     1       1.505  -2.693  -0.689  1.00  0.00           H  
HETATM   45  H16 UNL     1       3.563  -3.041   0.680  1.00  0.00           H  
HETATM   46  H17 UNL     1       1.809   1.490   0.022  1.00  0.00           H  
HETATM   47  H18 UNL     1       6.105   0.769   1.169  1.00  0.00           H  
HETATM   48  H19 UNL     1       5.587   0.804   2.941  1.00  0.00           H  
CONECT    1    2   30   31   32
CONECT    2    3   28
CONECT    3    4   33   34
CONECT    4    5    5    6
CONECT    6    7   18
CONECT    7    8   28   35
CONECT    8    9   36   37
CONECT    9   10   10   17
CONECT   10   11   18
CONECT   11   12   38
CONECT   12   13   13   17
CONECT   13   14   39
CONECT   14   15   15   40
CONECT   15   16   41
CONECT   16   17   17   42
CONECT   18   19   43
CONECT   19   20   20   24
CONECT   20   21   44
CONECT   21   22   22   45
CONECT   22   23   27
CONECT   23   24   24   25
CONECT   24   46
CONECT   25   26
CONECT   26   27   47   48
CONECT   28   29   29
END

HMDB0014958
     RDKit          3D
Tadalafil
 48 53  0  0  0  0  0  0  0  0999 V2000
   -3.4756   -4.2554    0.2896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4595   -3.2600   -0.0097 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2938   -3.6763   -0.7398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7767   -2.5519   -1.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232   -2.7340   -2.7331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7906   -1.2461   -0.9766 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9069   -0.8356   -0.1752 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4570    0.2047    0.8170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9627    1.3401    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0736    1.0695   -1.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2662    2.1744   -1.6627 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870    3.1998   -1.0431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3897    4.5404   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    5.4481   -0.5409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8871    4.9287    0.4950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8976    3.5814    0.7556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1475    2.6909   -0.0088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3069   -0.3649   -1.2307 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5070   -0.6144   -0.4372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0218   -1.8786   -0.2363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1732   -2.0525    0.5315 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8320   -0.9701    1.1128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3126    0.2885    0.9080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1693    0.4575    0.1451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1157    1.2201    1.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3183    0.5246    1.8987 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9607   -0.8454    1.9010 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -1.9345    0.4259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4844   -1.7024    1.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4199   -5.0674   -0.4744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4975   -3.7924    0.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2806   -4.6210    1.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5081   -4.5644   -1.3836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5328   -3.9813    0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5847   -0.2708   -0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292   -0.2091    1.4655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2557    0.5009    1.5184 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9110    2.2663   -2.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132    4.9153   -2.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1054    6.5182   -0.7642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4744    5.6052    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856    3.1539    1.5616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5951   -0.5290   -2.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5051   -2.6931   -0.6890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5626   -3.0408    0.6796 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8091    1.4901    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1049    0.7687    1.1690 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5870    0.8043    2.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 10 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  1  0
 26 27  1  0
  7 28  1  0
 28 29  2  0
 28  2  1  0
 18  6  1  0
 24 19  1  0
 17  9  1  0
 27 22  1  0
 17 12  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  7 35  1  6
  8 36  1  0
  8 37  1  0
 11 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  6
 20 44  1  0
 21 45  1  0
 24 46  1  0
 26 47  1  0
 26 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6R,12AR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione	ChEBI
(6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione	ChEBI
6-BENZO[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione	ChEBI
Adcirca	ChEBI
Cialis	ChEBI
Zalutia	Kegg
ICOS 351	HMDB
Tadanafil	HMDB
351, IC	HMDB

Chemical Formula

C₂₂H₁₉N₃O₄

Average Molecular Weight

389.404

Monoisotopic Molecular Weight

389.137556111

IUPAC Name

(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-1(10),11,13,15-tetraene-4,7-dione

Traditional Name

tadalafil

CAS Registry Number

171596-29-5

SMILES

[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1

InChI Key

WOXKDUGGOYFFRN-IIBYNOLFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Alpha-amino acid or derivatives
3-alkylindole
Benzodioxole
Indole
2,5-dioxopiperazine
Dioxopiperazine
N-methylpiperazine
N-alkylpiperazine
Benzenoid
Piperazine
1,4-diazinane
Tertiary carboxylic acid amide
Pyrrole
Heteroaromatic compound
Carboxamide group
Lactam
Acetal
Carboxylic acid derivative
Oxacycle
Azacycle
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:71940 )
pyrazinopyridoindole (CHEBI:71940 )

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: HMDB0014958)
Membrane (HMDB: HMDB0014958)

Source

Exogenous

Exogenous (HMDB: HMDB0014958)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	301 - 302 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.25 g/L	Not Available
LogP	1.7	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	189.4	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.25 g/L	ALOGPS
logP	2.36	ALOGPS
logP	1.64	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	15.17	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	74.87 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	104.08 m³·mol⁻¹	ChemAxon
Polarizability	40.92 Å³	ChemAxon
Number of Rings	6	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]+	187.812	31661259
DarkChem	[M-H]-	186.652	31661259
DeepCCS	[M-2H]-	222.841	30932474
DeepCCS	[M+Na]+	198.266	30932474
AllCCS	[M+H]+	192.7	32859911
AllCCS	[M+H-H2O]+	189.8	32859911
AllCCS	[M+NH4]+	195.3	32859911
AllCCS	[M+Na]+	196.0	32859911
AllCCS	[M-H]-	197.5	32859911
AllCCS	[M+Na-2H]-	197.1	32859911
AllCCS	[M+HCOO]-	196.8	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.	6.46 minutes	32390414
Predicted by Siyang on May 30, 2022	13.8185 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.88 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2420.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	191.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	559.4 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	607.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	130.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1163.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	507.2 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	1638.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	373.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	392.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	326.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	173.0 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tadalafil	[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1	5155.5	Standard polar	33892256
Tadalafil	[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1	3785.8	Standard non polar	33892256
Tadalafil	[H][C@]12CC3=C(NC4=CC=CC=C34)[C@H](N1C(=O)CN(C)C2=O)C1=CC2=C(OCO2)C=C1	3900.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tadalafil,1TMS,isomer #1	CN1CC(=O)N2[C@H](CC3=C([C@H]2C2=CC=C4OCOC4=C2)N([Si](C)(C)C)C2=CC=CC=C32)C1=O	3619.5	Semi standard non polar	33892256
Tadalafil,1TMS,isomer #1	CN1CC(=O)N2[C@H](CC3=C([C@H]2C2=CC=C4OCOC4=C2)N([Si](C)(C)C)C2=CC=CC=C32)C1=O	3613.8	Standard non polar	33892256
Tadalafil,1TMS,isomer #1	CN1CC(=O)N2[C@H](CC3=C([C@H]2C2=CC=C4OCOC4=C2)N([Si](C)(C)C)C2=CC=CC=C32)C1=O	4812.1	Standard polar	33892256
Tadalafil,1TBDMS,isomer #1	CN1CC(=O)N2[C@H](CC3=C([C@H]2C2=CC=C4OCOC4=C2)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)C1=O	3799.5	Semi standard non polar	33892256
Tadalafil,1TBDMS,isomer #1	CN1CC(=O)N2[C@H](CC3=C([C@H]2C2=CC=C4OCOC4=C2)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)C1=O	3866.6	Standard non polar	33892256
Tadalafil,1TBDMS,isomer #1	CN1CC(=O)N2[C@H](CC3=C([C@H]2C2=CC=C4OCOC4=C2)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C32)C1=O	4838.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tadalafil GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3097000000-803ff86b2ce502e2bc83	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tadalafil GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tadalafil 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 - Tadalafil LC-ESI-qTof , Positive-QTOF	splash10-02t9-2890000000-0be3708ad44a8a467cc5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil Linear Ion Trap , negative-QTOF	splash10-03di-0090000000-c52485d22b5893fc60a2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil Linear Ion Trap , negative-QTOF	splash10-03di-0090000000-2f6ad2194cd2932b0761	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil Linear Ion Trap , positive-QTOF	splash10-0i0r-0291000000-a4ae40141abccfc86710	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil Linear Ion Trap , positive-QTOF	splash10-0j59-0290000000-86095fe2d98833db9d0b	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil Linear Ion Trap , positive-QTOF	splash10-0uy0-0429200000-641774545afc89315134	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil Linear Ion Trap , positive-QTOF	splash10-0uy0-0429200000-f223c860e93cceeeacd8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil , positive-QTOF	splash10-014i-0292000000-0563bdd5b0be8c1cfa47	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil , positive-QTOF	splash10-02t9-2890000000-0be3708ad44a8a467cc5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 35V, Positive-QTOF	splash10-014i-0391000000-2d53d99ea189cbcf20bf	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 10V, Positive-QTOF	splash10-0f6x-0009000000-bea170f3de4098be75e0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 40V, Positive-QTOF	splash10-001i-0191000000-b10465a3e1f68719ab50	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 20V, Positive-QTOF	splash10-0udi-0019000000-989b326813e322333fa5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 20V, Negative-QTOF	splash10-004i-0119000000-28b2b617eb618183d5c8	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 40V, Negative-QTOF	splash10-001i-0791000000-5534e9b8d8ed5169e623	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 10V, Negative-QTOF	splash10-000i-0009000000-844cd3bb8e0273b1cadd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tadalafil 35V, Negative-QTOF	splash10-03di-0091000000-612762fb281177438c8e	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 10V, Positive-QTOF	splash10-0006-0009000000-cfa5abcf4ec76ea41d68	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 20V, Positive-QTOF	splash10-0006-1019000000-59cc81b34404c6ecd167	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 40V, Positive-QTOF	splash10-0006-0291000000-20d1a51d47c7345d5742	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 10V, Negative-QTOF	splash10-000i-2009000000-721840625f2b26eb19a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 20V, Negative-QTOF	splash10-052r-4019000000-5dff72997668963ef319	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 40V, Negative-QTOF	splash10-01pc-2191000000-f8bd70ef77444b35f09b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 10V, Positive-QTOF	splash10-0006-0029000000-5ec0e4346a39de6e6582	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tadalafil 20V, Positive-QTOF	splash10-0006-0009000000-565961b51e5cb53f55d4	2021-10-11	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 DB00820	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00820	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00820

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

99301

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tadalafil

METLIN ID

Not Available

PubChem Compound

110635

PDB ID

CIA

ChEBI ID

71940

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

Guazzi M, Samaja M: The role of PDE5-inhibitors in cardiopulmonary disorders: from basic evidence to clinical development. Curr Med Chem. 2007;14(20):2181-91. [PubMed:17691956 ]
Naeije R, Huez S: Expert opinion on available options treating pulmonary arterial hypertension. Expert Opin Pharmacother. 2007 Oct;8(14):2247-65. [PubMed:17927481 ]
Burnett AL: Molecular pharmacotherapeutic targeting of PDE5 for preservation of penile health. J Androl. 2008 Jan-Feb;29(1):3-14. Epub 2007 Oct 17. [PubMed:17942972 ]

Enzymes

Enzyme Details

1. cGMP-specific 3',5'-cyclic phosphodiesterase

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides. This phosphodiesterase catalyzes the specific hydrolysis of cGMP to 5'-GMP.
Gene Name:: PDE5A
Uniprot ID:: O76074
Molecular weight:: 99984.14

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Curran M, Keating G: Tadalafil. Drugs. 2003;63(20):2203-12; discussion 2213-4. [PubMed:14498756 ]
Eardley I, Cartledge J: Tadalafil (Cialis) for men with erectile dysfunction. Int J Clin Pract. 2002 May;56(4):300-4. [PubMed:12074215 ]
Montorsi F, Salonia A, Deho' F, Cestari A, Guazzoni G, Rigatti P, Stief C: Pharmacological management of erectile dysfunction. BJU Int. 2003 Mar;91(5):446-54. [PubMed:12603396 ]
Rotella DP: Tadalafil Lilly ICOS. Curr Opin Investig Drugs. 2003 Jan;4(1):60-5. [PubMed:12625031 ]
Roumeguere T, Sternon J, Schulman CC: [Erectile dysfunction and phosphodiesterase type 5 inhibitors]. Rev Med Brux. 2003 Jun;24(3):169-75. [PubMed:12891884 ]
Zoraghi R, Francis SH, Corbin JD: Critical amino acids in phosphodiesterase-5 catalytic site that provide for high-affinity interaction with cyclic guanosine monophosphate and inhibitors. Biochemistry. 2007 Nov 27;46(47):13554-63. Epub 2007 Nov 3. [PubMed:17979301 ]

Enzyme Details

2. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A

General function:: Involved in catalytic activity
Specific function:: Plays a role in signal transduction by regulating the intracellular concentration of cyclic nucleotides cAMP and cGMP. Catalyzes the hydrolysis of both cAMP and cGMP to 5'-AMP and 5'-GMP, respectively.
Gene Name:: PDE11A
Uniprot ID:: Q9HCR9
Molecular weight:: 55699.16

References

Weeks JL 2nd, Corbin JD, Francis SH: Interactions between cyclic nucleotide phosphodiesterase 11 catalytic site and substrates or tadalafil and role of a critical Gln-869 hydrogen bond. J Pharmacol Exp Ther. 2009 Oct;331(1):133-41. doi: 10.1124/jpet.109.156935. Epub 2009 Jul 29. [PubMed:19641165 ]
Weeks JL 2nd, Zoraghi R, Francis SH, Corbin JD: N-Terminal domain of phosphodiesterase-11A4 (PDE11A4) decreases affinity of the catalytic site for substrates and tadalafil, and is involved in oligomerization. Biochemistry. 2007 Sep 11;46(36):10353-64. Epub 2007 Aug 16. [PubMed:17696499 ]

Showing metabocard for Tadalafil (HMDB0014958)

MOL for HMDB0014958 (Tadalafil)

3D MOL for HMDB0014958 (Tadalafil)

3D SDF for HMDB0014958 (Tadalafil)

3D-SDF for HMDB0014958 (Tadalafil)

PDB for HMDB0014958 (Tadalafil)

3D PDB for HMDB0014958 (Tadalafil)

SMILES for HMDB0014958 (Tadalafil)

INCHI for HMDB0014958 (Tadalafil)

Structure for HMDB0014958 (Tadalafil)

3D Structure for HMDB0014958 (Tadalafil)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References