2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium

ID: ALA1482

Cas Number: 674-38-4

PubChem CID: 2370

Product Number: B608029, Order Now?

Max Phase: Approved

First Approval: 1948

Molecular Formula: C7H17N2O2+

Molecular Weight: 161.22

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bethanechol | bethanechol|674-38-4|Amidopropyldimethylbetaine|Carbamyl-beta-methylcholine|Carbamoyl-beta-methylcholine|(2-Hydroxypropyl)trimethylammonium carbamate|2-carbamoyloxypropyl-trimethylazanium|2-carbamoyloxypropyl(trimethyl)azanium|BRN 1773706|CHEBI:3084|UNII-004F72P8F4|2-((Aminocarbonyl)oxy)-N,N,N-trimethyl-1-propanaminium|Ammonium, (2-hydroxypropyl)trimethyl-, carbamate (ester)|2-carbamoyloxypropyl-trimethyl-azanium|004F72P8F4|2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium|1-PropanaShow More⌵

Synonyms from Alternative Forms(8): Bethanechol chloride | Carbamylmethylcholine chloride | NSC-30783 | Duvoid | Myocholine | Myotonachol | Myotonine | Urecholine

Canonical SMILES:  CC(C[N+](C)(C)C)OC(N)=O

Standard InChI:  InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1

Standard InChI Key:  NZUPCNDJBJXXRF-UHFFFAOYSA-O

Molfile:  

     RDKit          2D

 11 10  0  0  0  0  0  0  0  0999 V2000
    4.3667   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9042   -1.6875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7542   -1.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3667   -2.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917   -1.3375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500   -2.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2958   -1.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  1  1  0
  4  1  2  0
  5  1  1  0
  6  7  1  0
  7  3  1  0
  8  2  1  0
  9  2  1  0
 10  2  1  0
 11  7  1  0
M  CHG  1   2   1
M  END

Alternative Forms

1. Parent:

   

   ALA1482

   bethanechol

2. Alternative Forms:

   

   ALA1482

   Bethanechol Chloride

Molecule Features

Natural Product: No

Oral: Yes

Chemical Probe: No

Parenteral: Yes

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: Yes

Prodrug: No

Calculated Properties

Molecular Weight: 161.22

Molecular Weight (Monoisotopic): 161.1285

AlogP: 0.18

#Rotatable Bonds: 3

Polar Surface Area: 52.32

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: -4.14

CX LogD: -4.14

Aromatic Rings: ┄

Heavy Atoms: 11

QED Weighted: 0.60

Np Likeness Score: 0.89

References

1. Dallanoce C, De Amici M, Barocelli E, Bertoni S, Roth BL, Ernsberger P, De Micheli C..  (2007)  Novel oxotremorine-related heterocyclic derivatives: Synthesis and in vitro pharmacology at the muscarinic receptor subtypes.,  15  (24): [PMID:17889543] [10.1016/j.bmc.2007.09.003]

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. Chen M, Vijay V, Shi Q, Liu Z, Fang H, Tong W..  (2011)  FDA-approved drug labeling for the study of drug-induced liver injury.,  16  (15-16): [PMID:21624500] [10.1016/j.drudis.2011.05.007]

5. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

6. Bolchi C, Valoti E, Binda M, Fasoli F, Ferrara R, Fumagalli L, Gotti C, Matucci R, Vistoli G, Pallavicini M..  (2013)  Design, synthesis and binding affinity of acetylcholine carbamoyl analogues.,  23  (23): [PMID:24128660] [10.1016/j.bmcl.2013.09.023]

7. Matera C, Flammini L, Quadri M, Vivo V, Ballabeni V, Holzgrabe U, Mohr K, De Amici M, Barocelli E, Bertoni S, Dallanoce C..  (2014)  Bis(ammonio)alkane-type agonists of muscarinic acetylcholine receptors: synthesis, in vitro functional characterization, and in vivo evaluation of their analgesic activity.,  75  [PMID:24534538] [10.1016/j.ejmech.2014.01.032]

8. PubChem BioAssay data set, 

9. WHO Anatomical Therapeutic Chemical Classification, 

10. Warner DJ, Chen H, Cantin LD, Kenna JG, Stahl S, Walker CL, Noeske T..  (2012)  Mitigating the inhibition of human bile salt export pump by drugs: opportunities provided by physicochemical property modulation, in silico modeling, and structural modification.,  40  (12): [PMID:22961681] [10.1124/dmd.112.047068]

11. Chen M, Suzuki A, Thakkar S, Yu K, Hu C, Tong W..  (2016)  DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans.,  21  (4): [PMID:26948801] [10.1016/j.drudis.2016.02.015]

12. Unpublished dataset, 

13. Katie Heiser, Peter F. McLean, Chadwick T. Davis, Ben Fogelson, Hannah B. Gordon, Pamela Jacobson, Brett Hurst, Ben Miller, Ronald W. Alfa, Berton A. Earnshaw, Mason L. Victors, Yolanda T. Chong, Imran S. Haque, Adeline S. Low, Christopher C. Gibson.  (2020)  Identification of potential treatments for COVID-19 through artificial intelligence-enabled phenomic analysis of human cells infected with SARS-CoV-2,  [10.1101/2020.04.21.054387]

14. Ellen Van Damme.  (2021)  Screening of ~5500 FDA-approved drugs and clinical candidates for anti-SARS-CoV-2 activity,  [10.6019/CHEMBL4651402]

15. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]

16. Sutherland JJ, Yonchev D, Fekete A, Urban L..  (2023)  A preclinical secondary pharmacology resource illuminates target-adverse drug reaction associations of marketed drugs.,  14  (1): [PMID:37468498] [10.1038/s41467-023-40064-9]

Source

Source(7):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• WHO Anatomical Therapeutic Chemical Classification
• SARS-CoV-2 Screening Data 2020-21
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6