SID26663897

ID: ALA1066

Chembl Id: CHEMBL1066

Max Phase: Preclinical

Molecular Formula: C16H25NO2

Molecular Weight: 263.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rel-Tramadol

Synonyms from Alternative Forms(2): CG-315E | U-26225A

Canonical SMILES:  COc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1

Standard InChI:  InChI=1S/C16H25NO2/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3/t14-,16+/m1/s1

Standard InChI Key:  TVYLLZQTGLZFBW-ZBFHGGJFSA-N

Alternative Forms

1. Parent:

   

   ALA1066

   (R,R)-TRAMADOL

2. Alternative Forms:

   

   ALA1066

   (1R,2R)-2-[(dimethylamino)methyl]-1-[3-(trideuteriomethoxy)phenyl]cyclohexan-1-ol
3. 

   ALA1066

   (1R,2R)-2-[[bis(trideuteriomethyl)amino]methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
4. 

   ALA1066

   (1R,2R)-2-[[bis(trideuteriomethyl)amino]methyl]-1-[3-(trideuteriomethoxy)phenyl]cyclohexan-1-ol
5. 

   ALA1066

   Tramadol hydrochloride

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 263.38

Molecular Weight (Monoisotopic): 263.1885

AlogP: 2.63

#Rotatable Bonds: 4

Polar Surface Area: 32.70

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.80

CX Basic pKa: 9.23

CX LogP: 2.45

CX LogD: 0.62

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.91

Np Likeness Score: 0.43

References

1. PubChem BioAssay data set, 

2. PubChem BioAssay data set, 

3. PubChem BioAssay data set, 

4. PubChem BioAssay data set, 

5. PubChem BioAssay data set, 

6. Shen Q, Qian Y, Huang X, Xu X, Li W, Liu J, Fu W..  (2016)  Discovery of Potent and Selective Agonists of δ Opioid Receptor by Revisiting the "Message-Address" Concept.,  7  (4): [PMID:27096047] [10.1021/acsmedchemlett.5b00423]

7. Meyer MJ, Neumann VE, Friesacher HR, Zdrazil B, Brockmöller J, Tzvetkov MV..  (2019)  Opioids as Substrates and Inhibitors of the Genetically Highly Variable Organic Cation Transporter OCT1.,  62  (21): [PMID:31597043] [10.1021/acs.jmedchem.9b01301]

8. Bhuniya D, Kharul RK, Hajare A, Shaikh N, Bhosale S, Balwe S, Begum F, De S, Athavankar S, Joshi D, Madgula V, Joshi K, Raje AA, Meru AV, Magdum A, Mookhtiar KA, Barbhaiya R..  (2019)  Discovery and evaluation of novel FAAH inhibitors in neuropathic pain model.,  29  (2): [PMID:30503633] [10.1016/j.bmcl.2018.11.048]

9. Huang H,Wang W,Xu X,Zhu C,Wang Y,Liu J,Li W,Fu W.  (2020)  Discovery of 3-((dimethylamino)methyl)-4-hydroxy-4-(3-methoxyphenyl)-N-phenylpiperidine-1-carboxamide as novel potent analgesic.,  189  [PMID:31982651] [10.1016/j.ejmech.2020.112070]

10. Huang H, Li X, Xie P, Li X, Xu X, Qian Y, Yuan C, Meng X, Chai J, Chen J, Liu J, Wang W, Li W, Wang Y, Fu W, Liu J..  (2021)  Discovery, Structure-Activity Relationship, and Mechanistic Studies of 1-((3R,4S)-3-((Dimethylamino)methyl)-4-hydroxy-4-(3-methoxyphenyl)piperidin-1-yl)-2-(2,4,5-trifluorophenyl)ethan-1-one as a Novel Potent Analgesic.,  64  (13.0): [PMID:34152138] [10.1021/acs.jmedchem.1c00722]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays