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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 02:51:45 UTC

HMDB ID

HMDB0014808

Secondary Accession Numbers

HMDB14808

Metabolite Identification

Common Name

Pirenzepine

Description

Pirenzepine, also known as ulcoprotect or gastrozepin, belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine. Pirenzepine is a drug which is used for the treatment of peptic ulcer, gastric ulcer, and duodenal ulcer. It is in a class of drugs known as muscarinic receptor antagonists - acetylcholine being the neurotransmitter of the parasympathetic nervous system which initiates the rest-and-digest state (as opposed to fight-or-flight), resulting in an increase in gastric motility and digestion; whereas pirenzepine would inhibit these actions and cause decreased gastric motility leading to delayed gastric emptying and constipation. Pirenzepine is a very strong basic compound (based on its pKa). In humans, pirenzepine is involved in pirenzepine action pathway. Pirenzepine has been investigated for use in myopia control. Pirenzepine (Gastrozepin), an M1 selective antagonist, is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm. It promotes the homodimerization or oligomerisation of M1 receptors. It has no effects on the brain and spinal cord as it cannot diffuse through the blood–brain barrier.

Structure

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

670
  Mrv0541 02231214552D          

 26 29  0  0  0  0            999 V2000
    4.7423   -0.2440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576    3.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -1.0689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -2.7186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.9934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4404    2.8003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919    0.7572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -1.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -1.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -2.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -2.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -0.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -3.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848    1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7712    1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1012    2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547    2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    2.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    2.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061    1.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2149    1.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2 20  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6 18  1  0  0  0  0
  6 20  1  0  0  0  0
  7 16  1  0  0  0  0
  7 26  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 15 17  1  0  0  0  0
 15 19  2  0  0  0  0
 16 18  2  0  0  0  0
 17 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0014808
     RDKit          3D
Pirenzepine
 47 50  0  0  0  0  0  0  0  0999 V2000
    5.0877    1.1038    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7539   -0.2936    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6888   -0.5085    1.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781   -1.1135    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934   -0.4397   -0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -0.5169   -0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150    0.2017    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    0.7941    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812    0.3594   -0.0746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1714   -0.0388   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4559    0.3121   -2.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -0.0016   -3.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1247   -0.6803   -3.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8315   -1.0209   -2.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585   -0.7018   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794   -1.0650   -0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0457   -2.0041   -0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364   -0.4173    0.9570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316    0.5044    1.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9192    1.0634    2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1338    1.9622    3.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874    2.2587    2.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    1.7025    1.8005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1763    0.8386    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -0.4753   -1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -0.9393   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    1.5253   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678    1.2581    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945    1.6100    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431    0.4850    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0022   -1.1450    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400   -1.1121    1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -2.1734    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5661   -1.6303   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660   -0.4131   -1.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    0.8892   -2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525    0.2712   -4.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4950   -0.9322   -4.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788   -1.5501   -2.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1618   -0.6491    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9045    0.7909    3.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    2.3993    4.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2932    2.9625    3.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4003    0.4790   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188   -1.2471   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3115   -0.6649   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5170   -2.0374   -0.5925 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  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
 16 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
  5 25  1  0
 25 26  1  0
 26  2  1  0
 24  9  1  0
 15 10  1  0
 24 19  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
M  END

670
  Mrv0541 02231214552D          

 26 29  0  0  0  0            999 V2000
    4.7423   -0.2440    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2576    3.5435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -1.0689    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -2.7186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.9934    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4404    2.8003    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3919    0.7572    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -1.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -1.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5991   -2.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280   -2.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3136   -0.2440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3135   -3.5435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.1685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2848    1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7712    1.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1012    2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9547    2.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6639    0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6155    2.8003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841    2.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7717    2.4213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8410    1.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6498    1.8419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4061    1.8418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2149    1.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  2 20  2  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  3 12  1  0  0  0  0
  4 10  1  0  0  0  0
  4 11  1  0  0  0  0
  4 13  1  0  0  0  0
  5 14  1  0  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  6 18  1  0  0  0  0
  6 20  1  0  0  0  0
  7 16  1  0  0  0  0
  7 26  2  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 12 14  1  0  0  0  0
 15 17  1  0  0  0  0
 15 19  2  0  0  0  0
 16 18  2  0  0  0  0
 17 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 23  1  0  0  0  0
 21 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014808

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)

> <INCHI_KEY>
RMHMFHUVIITRHF-UHFFFAOYSA-N

> <FORMULA>
C19H21N5O2

> <MOLECULAR_WEIGHT>
351.4023

> <EXACT_MASS>
351.169524941

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
37.112802132135535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

> <ALOGPS_LOGP>
1.26

> <JCHEM_LOGP>
0.8524512625648508

> <ALOGPS_LOGS>
-2.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.00982979880011

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.574185364235227

> <JCHEM_PKA_STRONGEST_BASIC>
7.592644342960564

> <JCHEM_POLAR_SURFACE_AREA>
68.78

> <JCHEM_REFRACTIVITY>
100.92570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
pirenzepine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014808
     RDKit          3D
Pirenzepine
 47 50  0  0  0  0  0  0  0  0999 V2000
    5.0877    1.1038    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7539   -0.2936    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6888   -0.5085    1.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781   -1.1135    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934   -0.4397   -0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -0.5169   -0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150    0.2017    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    0.7941    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812    0.3594   -0.0746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1714   -0.0388   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4559    0.3121   -2.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -0.0016   -3.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1247   -0.6803   -3.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8315   -1.0209   -2.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585   -0.7018   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794   -1.0650   -0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0457   -2.0041   -0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364   -0.4173    0.9570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316    0.5044    1.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9192    1.0634    2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1338    1.9622    3.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874    2.2587    2.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    1.7025    1.8005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1763    0.8386    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -0.4753   -1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -0.9393   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    1.5253   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678    1.2581    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945    1.6100    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431    0.4850    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0022   -1.1450    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400   -1.1121    1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -2.1734    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5661   -1.6303   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660   -0.4131   -1.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    0.8892   -2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525    0.2712   -4.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4950   -0.9322   -4.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788   -1.5501   -2.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1618   -0.6491    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9045    0.7909    3.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    2.3993    4.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2932    2.9625    3.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4003    0.4790   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188   -1.2471   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3115   -0.6649   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5170   -2.0374   -0.5925 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  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
 16 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
  5 25  1  0
 25 26  1  0
 26  2  1  0
 24  9  1  0
 15 10  1  0
 24 19  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 670                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       8.852  -0.455   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       6.081   6.615   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       6.185  -1.995   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0       6.185  -5.075   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.519   1.854   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       8.289   5.227   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      10.065   1.413   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       4.852  -2.765   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.519  -2.765   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.852  -4.305   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.519  -4.305   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.185  -0.455   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.185  -6.615   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.519   0.314   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.132   2.522   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.906   2.522   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.789   4.023   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.249   4.023   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.973   1.413   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.749   5.227   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.264   4.520   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.774   4.520   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.436   1.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.080   3.438   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.958   3.438   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.601   1.874   0.000  0.00  0.00           C+0
CONECT    1   14                                                            
CONECT    2   20                                                            
CONECT    3    8    9   12                                                  
CONECT    4   10   11   13                                                  
CONECT    5   14   15   16                                                  
CONECT    6   18   20                                                       
CONECT    7   16   26                                                       
CONECT    8    3   10                                                       
CONECT    9    3   11                                                       
CONECT   10    4    8                                                       
CONECT   11    4    9                                                       
CONECT   12    3   14                                                       
CONECT   13    4                                                            
CONECT   14    1    5   12                                                  
CONECT   15    5   17   19                                                  
CONECT   16    5    7   18                                                  
CONECT   17   15   20   21                                                  
CONECT   18    6   16   22                                                  
CONECT   19   15   23                                                       
CONECT   20    2    6   17                                                  
CONECT   21   17   24                                                       
CONECT   22   18   25                                                       
CONECT   23   19   24                                                       
CONECT   24   21   23                                                       
CONECT   25   22   26                                                       
CONECT   26    7   25                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

COMPND    HMDB0014808
HETATM    1  C1  UNL     1       5.088   1.104   0.390  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.754  -0.294   0.551  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.689  -0.508   1.508  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.478  -1.113   0.875  1.00  0.00           C  
HETATM    5  N2  UNL     1       2.193  -0.440  -0.340  1.00  0.00           N  
HETATM    6  C4  UNL     1       0.835  -0.517  -0.814  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.115   0.202   0.012  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.430   0.794   1.034  1.00  0.00           O  
HETATM    9  N3  UNL     1      -1.481   0.359  -0.075  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.171  -0.039  -1.254  1.00  0.00           C  
HETATM   11  C7  UNL     1      -1.456   0.312  -2.392  1.00  0.00           C  
HETATM   12  C8  UNL     1      -1.919  -0.002  -3.642  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.125  -0.680  -3.822  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.831  -1.021  -2.688  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.358  -0.702  -1.432  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.279  -1.065  -0.333  1.00  0.00           C  
HETATM   17  O2  UNL     1      -5.046  -2.004  -0.585  1.00  0.00           O  
HETATM   18  N4  UNL     1      -4.336  -0.417   0.957  1.00  0.00           N  
HETATM   19  C13 UNL     1      -3.432   0.504   1.579  1.00  0.00           C  
HETATM   20  C14 UNL     1      -3.919   1.063   2.757  1.00  0.00           C  
HETATM   21  C15 UNL     1      -3.134   1.962   3.466  1.00  0.00           C  
HETATM   22  C16 UNL     1      -1.887   2.259   2.955  1.00  0.00           C  
HETATM   23  N5  UNL     1      -1.426   1.703   1.801  1.00  0.00           N  
HETATM   24  C17 UNL     1      -2.176   0.839   1.115  1.00  0.00           C  
HETATM   25  C18 UNL     1       3.192  -0.475  -1.337  1.00  0.00           C  
HETATM   26  C19 UNL     1       4.492  -0.939  -0.716  1.00  0.00           C  
HETATM   27  H1  UNL     1       4.505   1.525  -0.453  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.168   1.258   0.166  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.894   1.610   1.356  1.00  0.00           H  
HETATM   30  H4  UNL     1       3.443   0.485   1.939  1.00  0.00           H  
HETATM   31  H5  UNL     1       4.002  -1.145   2.352  1.00  0.00           H  
HETATM   32  H6  UNL     1       1.640  -1.112   1.585  1.00  0.00           H  
HETATM   33  H7  UNL     1       2.764  -2.173   0.602  1.00  0.00           H  
HETATM   34  H8  UNL     1       0.566  -1.630  -0.658  1.00  0.00           H  
HETATM   35  H9  UNL     1       0.866  -0.413  -1.881  1.00  0.00           H  
HETATM   36  H10 UNL     1      -0.559   0.889  -2.254  1.00  0.00           H  
HETATM   37  H11 UNL     1      -1.352   0.271  -4.532  1.00  0.00           H  
HETATM   38  H12 UNL     1      -3.495  -0.932  -4.805  1.00  0.00           H  
HETATM   39  H13 UNL     1      -4.779  -1.550  -2.740  1.00  0.00           H  
HETATM   40  H14 UNL     1      -5.162  -0.649   1.537  1.00  0.00           H  
HETATM   41  H15 UNL     1      -4.905   0.791   3.105  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.510   2.399   4.380  1.00  0.00           H  
HETATM   43  H17 UNL     1      -1.293   2.963   3.528  1.00  0.00           H  
HETATM   44  H18 UNL     1       3.400   0.479  -1.852  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.919  -1.247  -2.096  1.00  0.00           H  
HETATM   46  H20 UNL     1       5.312  -0.665  -1.410  1.00  0.00           H  
HETATM   47  H21 UNL     1       4.517  -2.037  -0.593  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   26
CONECT    3    4   30   31
CONECT    4    5   32   33
CONECT    5    6   25
CONECT    6    7   34   35
CONECT    7    8    8    9
CONECT    9   10   24
CONECT   10   11   11   15
CONECT   11   12   36
CONECT   12   13   13   37
CONECT   13   14   38
CONECT   14   15   15   39
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19   40
CONECT   19   20   20   24
CONECT   20   21   41
CONECT   21   22   22   42
CONECT   22   23   43
CONECT   23   24   24
CONECT   25   26   44   45
CONECT   26   46   47
END

HMDB0014808
     RDKit          3D
Pirenzepine
 47 50  0  0  0  0  0  0  0  0999 V2000
    5.0877    1.1038    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7539   -0.2936    0.5509 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6888   -0.5085    1.5081 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781   -1.1135    0.8747 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1934   -0.4397   -0.3405 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8351   -0.5169   -0.8141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1150    0.2017    0.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    0.7941    1.0343 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4812    0.3594   -0.0746 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1714   -0.0388   -1.2543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4559    0.3121   -2.3916 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191   -0.0016   -3.6416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1247   -0.6803   -3.8215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8315   -1.0209   -2.6880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3585   -0.7018   -1.4319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2794   -1.0650   -0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0457   -2.0041   -0.5846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3364   -0.4173    0.9570 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4316    0.5044    1.5791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9192    1.0634    2.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1338    1.9622    3.4656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8874    2.2587    2.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4258    1.7025    1.8005 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1763    0.8386    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1925   -0.4753   -1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -0.9393   -0.7158 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5048    1.5253   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1678    1.2581    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8945    1.6100    1.3560 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4431    0.4850    1.9386 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0022   -1.1450    2.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6400   -1.1121    1.5854 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7642   -2.1734    0.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5661   -1.6303   -0.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660   -0.4131   -1.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    0.8892   -2.2542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3525    0.2712   -4.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4950   -0.9322   -4.8046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7788   -1.5501   -2.7400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1618   -0.6491    1.5374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9045    0.7909    3.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5098    2.3993    4.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2932    2.9625    3.5276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4003    0.4790   -1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9188   -1.2471   -2.0958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3115   -0.6649   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5170   -2.0374   -0.5925 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
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  2  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
 16 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
  5 25  1  0
 25 26  1  0
 26  2  1  0
 24  9  1  0
 15 10  1  0
 24 19  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  0
  3 31  1  0
  4 32  1  0
  4 33  1  0
  6 34  1  0
  6 35  1  0
 11 36  1  0
 12 37  1  0
 13 38  1  0
 14 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 25 44  1  0
 25 45  1  0
 26 46  1  0
 26 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
11-((4-Methyl-1-piperazinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one	ChEBI
Pirenzepina	ChEBI
Pirenzepinum	ChEBI
Dihydrochloride, pirenzepine	HMDB
Ulcoprotect	HMDB
Dolorgiet brand OF pirenzepine dihydrochloride	HMDB
Gastrozepin	HMDB
Piren basan	HMDB
Piren-basan	HMDB
Pirenzepin ratiopharm	HMDB
Pirenzepin-ratiopharm	HMDB
Pirenzepine dihydrochloride	HMDB
Gastrotsepin	HMDB
Pirenzepin	HMDB
Ulgescum	HMDB
CT-Arzneimittel brand OF pirenzepine dihydrochloride	HMDB
Pirenzepin von CT	HMDB
Ratiopharm brand OF pirenzepine dihydrochloride	HMDB
Azupharma brand OF pirenzepine dihydrochloride	HMDB
Boehringer ingelheim brand OF pirenzepine dihydrochloride	HMDB
L-S 519	HMDB
Pyrenzepine	HMDB
Sagitta brand OF pirenzepine dihydrochloride	HMDB
Von CT, pirenzepin	HMDB

Chemical Formula

C₁₉H₂₁N₅O₂

Average Molecular Weight

351.4023

Monoisotopic Molecular Weight

351.169524941

IUPAC Name

2-[2-(4-methylpiperazin-1-yl)acetyl]-2,4,9-triazatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-10-one

Traditional Name

pirenzepine

CAS Registry Number

28797-61-7

SMILES

CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1

InChI Identifier

InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)

InChI Key

RMHMFHUVIITRHF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-benzodiazepines. These are organic compounds containing a benzene ring fused to a 1,4-azepine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodiazepines

Sub Class

1,4-benzodiazepines

Direct Parent

1,4-benzodiazepines

Alternative Parents

Substituents

Pyrido-para-diazepine
1,4-benzodiazepine
Alpha-amino acid or derivatives
N-piperazineacetamide
N-methylpiperazine
N-alkylpiperazine
1,4-diazinane
Piperazine
Pyridine
Imidolactam
Benzenoid
Heteroaromatic compound
Cyclic carboximidic acid
Tertiary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Tertiary amine
Tertiary aliphatic amine
Azacycle
Carboxylic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pyridobenzodiazepine (CHEBI:8247 )

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

Membrane (HMDB: HMDB0014808)

Source

Exogenous

Exogenous (HMDB: HMDB0014808)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Pirenzepine Action Pathway (PathBank: SMP0000246)

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	0.68 g/L	Not Available
LogP	0.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	Not Available	181.172	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000921

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.68 g/L	ALOGPS
logP	1.26	ALOGPS
logP	0.85	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.57	ChemAxon
pKa (Strongest Basic)	7.59	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.78 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	100.93 m³·mol⁻¹	ChemAxon
Polarizability	37.11 Å³	ChemAxon
Number of Rings	4	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]+	182.343	31661259
DarkChem	[M-H]-	180.069	31661259
DeepCCS	[M+H]+	186.484	30932474
DeepCCS	[M-H]-	184.126	30932474
DeepCCS	[M-2H]-	218.429	30932474
DeepCCS	[M+Na]+	193.781	30932474
AllCCS	[M+H]+	183.0	32859911
AllCCS	[M+H-H2O]+	180.0	32859911
AllCCS	[M+NH4]+	185.8	32859911
AllCCS	[M+Na]+	186.6	32859911
AllCCS	[M-H]-	184.4	32859911
AllCCS	[M+Na-2H]-	184.1	32859911
AllCCS	[M+HCOO]-	183.8	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.	1.91 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7895 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.08 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	268.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	537.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	200.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	85.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	155.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	47.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	220.5 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	359.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	724.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	614.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	54.5 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	864.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	182.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	464.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	413.7 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	318.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pirenzepine	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1	4076.7	Standard polar	33892256
Pirenzepine	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1	2972.4	Standard non polar	33892256
Pirenzepine	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC3=C2N=CC=C3)CC1	3077.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pirenzepine,1TMS,isomer #1	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C)C3=CC=CN=C32)CC1	2846.4	Semi standard non polar	33892256
Pirenzepine,1TMS,isomer #1	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C)C3=CC=CN=C32)CC1	2924.1	Standard non polar	33892256
Pirenzepine,1TMS,isomer #1	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C)C3=CC=CN=C32)CC1	4326.0	Standard polar	33892256
Pirenzepine,1TBDMS,isomer #1	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=CN=C32)CC1	3033.5	Semi standard non polar	33892256
Pirenzepine,1TBDMS,isomer #1	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=CN=C32)CC1	3129.6	Standard non polar	33892256
Pirenzepine,1TBDMS,isomer #1	CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)N([Si](C)(C)C(C)(C)C)C3=CC=CN=C32)CC1	4385.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pirenzepine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9274000000-86b6dd314412cb49103e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirenzepine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pirenzepine 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 - Pirenzepine 10V, Positive-QTOF	splash10-0ik9-0869000000-07871a195a1b07560aaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 20V, Positive-QTOF	splash10-03di-2920000000-f203c4e307f7cbb9ccba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 40V, Positive-QTOF	splash10-01ox-9730000000-81e7602ee0e57b11f329	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 10V, Negative-QTOF	splash10-0udi-0039000000-eba2d6236adedf16c650	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 20V, Negative-QTOF	splash10-0ik9-0295000000-d2fe7d74f38b69f23111	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 40V, Negative-QTOF	splash10-03xr-1960000000-11b9714bc5655d979a4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 10V, Positive-QTOF	splash10-0udi-0209000000-abe020ee7c3bd795b260	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 20V, Positive-QTOF	splash10-0w29-1429000000-17de4fa81cf69470057b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 40V, Positive-QTOF	splash10-03kc-9230000000-b37f79f5ccdc399c3a22	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 10V, Negative-QTOF	splash10-0udi-0029000000-6d0cde8b33849d6a8df7	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 20V, Negative-QTOF	splash10-0w29-0059000000-c5eade40c8f67c093c19	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pirenzepine 40V, Negative-QTOF	splash10-0bt9-0090000000-ca4cb52f06eeaadb0754	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Pirenzepine Action Pathway		Not Available

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 DB00670	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00670	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00670

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4682

KEGG Compound ID

C07508

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pirenzepine

METLIN ID

Not Available

PubChem Compound

4848

PDB ID

Not Available

ChEBI ID

8247

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

Czepita D: [Fundamentals of modern treatment of myopia]. Ann Acad Med Stetin. 2005;51(2):5-9. [PubMed:16519089 ]

Enzymes

Enzyme Details

1. Muscarinic acetylcholine receptor M1

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover
Gene Name:: CHRM1
Uniprot ID:: P11229
Molecular weight:: 51420.4

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Pedretti RF, Prete G, Foreman RD, Adamson PB, Vanoli E: Autonomic modulation during acute myocardial ischemia by low-dose pirenzepine in conscious dogs with a healed myocardial infarction: a comparison with beta-adrenergic blockade. J Cardiovasc Pharmacol. 2003 May;41(5):671-7. [PubMed:12717096 ]

Showing metabocard for Pirenzepine (HMDB0014808)

MOL for HMDB0014808 (Pirenzepine)

3D MOL for HMDB0014808 (Pirenzepine)

3D SDF for HMDB0014808 (Pirenzepine)

3D-SDF for HMDB0014808 (Pirenzepine)

PDB for HMDB0014808 (Pirenzepine)

3D PDB for HMDB0014808 (Pirenzepine)

SMILES for HMDB0014808 (Pirenzepine)

INCHI for HMDB0014808 (Pirenzepine)

Structure for HMDB0014808 (Pirenzepine)

3D Structure for HMDB0014808 (Pirenzepine)

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