Metabolite Tadalafil catechol metabolite

Name

Tadalafil catechol metabolite

Description

Not Available

Structure

Similar Structures

Synonyms

Not Available

UNII

Not Available

CAS number

Not Available

Weight

Average: 389.404
Monoisotopic: 389.137556111

Chemical Formula

C₂₂H₁₉N₃O₄

InChI Key

WOXKDUGGOYFFRN-IIBYNOLFSA-N

InChI

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

IUPAC Name

(2R,8R)-2-(2H-1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-1(10),11,13,15-tetraene-4,7-dione

SMILES

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

Reactions

Tadalafil

Tadalafil catechol metabolite
- Tadalafil catechol metabolite
  
  Tadalafil methylcatechol metabolite
  - Tadalafil methylcatechol metabolite
    
    Tadalafil methylcatechol glucuronide metabolite

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0006-3097000000-803ff86b2ce502e2bc83
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-02t9-2890000000-0be3708ad44a8a467cc5
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-03di-0090000000-c52485d22b5893fc60a2
MS/MS Spectrum - Linear Ion Trap , negative	LC-MS/MS	splash10-03di-0090000000-2f6ad2194cd2932b0761
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0i0r-0291000000-a4ae40141abccfc86710
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0j59-0290000000-86095fe2d98833db9d0b
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0uy0-0429200000-641774545afc89315134
MS/MS Spectrum - Linear Ion Trap , positive	LC-MS/MS	splash10-0uy0-0429200000-f223c860e93cceeeacd8
MS/MS Spectrum - , positive	LC-MS/MS	splash10-014i-0292000000-0563bdd5b0be8c1cfa47
MS/MS Spectrum - , positive	LC-MS/MS	splash10-02t9-2890000000-0be3708ad44a8a467cc5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0009000000-fac40b479b8719ddcf10
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0009000000-2bfea16a9b34bf12e300
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01ox-0029000000-a4bcb4f2924fd2251047
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03dr-0097000000-5e182f472b0efd7e614b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0cdr-2069000000-b5e53bce569a11384047
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0296-0039000000-5aa6c648eebf1173d0a9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0006-0009000000-fac40b479b8719ddcf10
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0009000000-2bfea16a9b34bf12e300
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-01ox-0029000000-a4bcb4f2924fd2251047
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0296-0039000000-5aa6c648eebf1173d0a9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-03dr-0097000000-5e182f472b0efd7e614b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0cdr-2069000000-b5e53bce569a11384047
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	206.8616357	predicted	DarkChem Lite v0.1.0
[M-H]-	206.5738357	predicted	DarkChem Lite v0.1.0
[M-H]-	189.95772	predicted	DeepCCS 1.0 (2019)
[M-H]-	206.8616357	predicted	DarkChem Lite v0.1.0
[M-H]-	206.5738357	predicted	DarkChem Lite v0.1.0
[M-H]-	189.95772	predicted	DeepCCS 1.0 (2019)
[M+H]+	207.2695357	predicted	DarkChem Lite v0.1.0
[M+H]+	206.7156357	predicted	DarkChem Lite v0.1.0
[M+H]+	192.35329	predicted	DeepCCS 1.0 (2019)
[M+H]+	207.2695357	predicted	DarkChem Lite v0.1.0
[M+H]+	206.7156357	predicted	DarkChem Lite v0.1.0
[M+H]+	192.35329	predicted	DeepCCS 1.0 (2019)
[M+Na]+	206.6459357	predicted	DarkChem Lite v0.1.0
[M+Na]+	198.26581	predicted	DeepCCS 1.0 (2019)
[M+Na]+	206.6459357	predicted	DarkChem Lite v0.1.0
[M+Na]+	198.26581	predicted	DeepCCS 1.0 (2019)

External Links

Human Metabolome Database: HMDB0014958
ChemSpider: 99301
BindingDB: 14777
ChEBI: 71940
ChEMBL: CHEMBL779
ZINC: ZINC000003993855
PharmGKB: PA10333
PDBe Ligand: CIA

Predicted Properties

Property	Value	Source
Water Solubility	0.25 mg/mL	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	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Metabolite Tadalafil catechol metabolite

Structure for Tadalafil catechol metabolite

Collision Cross Sections (CCS)