4-(4-(2-amoethinyl)-2-iodophenoxy)phenol

ID: ALA1182312

Chembl Id: CHEMBL1182312

Cas Number: 712349-95-6

PubChem CID: 9950514

Max Phase: Preclinical

Molecular Formula: C14H14INO2

Molecular Weight: 355.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NCCc1ccc(Oc2ccc(O)cc2)c(I)c1

Standard InChI:  InChI=1S/C14H14INO2/c15-13-9-10(7-8-16)1-6-14(13)18-12-4-2-11(17)3-5-12/h1-6,9,17H,7-8,16H2

Standard InChI Key:  XIINYOJWNGOUPF-UHFFFAOYSA-N

Alternative Forms

1. Alternative Forms:

   

   ALA1182312

   3-Iodothyronamine Hydrochloride

2. Parent:

   

   ALA1182312

   3-Iodothyronamine

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: 355.18

Molecular Weight (Monoisotopic): 355.0069

AlogP: 3.29

#Rotatable Bonds: 4

Polar Surface Area: 55.48

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.43

CX Basic pKa: 10.04

CX LogP: 2.88

CX LogD: 1.25

Aromatic Rings: 2

Heavy Atoms: 18

QED Weighted: 0.83

Np Likeness Score: 0.28

References

1. Lewin AH, Miller GM, Gilmour B..  (2011)  Trace amine-associated receptor 1 is a stereoselective binding site for compounds in the amphetamine class.,  19  (23): [PMID:22037049] [10.1016/j.bmc.2011.10.007]

2. Chiellini G, Nesi G, Digiacomo M, Malvasi R, Espinoza S, Sabatini M, Frascarelli S, Laurino A, Cichero E, Macchia M, Gainetdinov RR, Fossa P, Raimondi L, Zucchi R, Rapposelli S..  (2015)  Design, Synthesis, and Evaluation of Thyronamine Analogues as Novel Potent Mouse Trace Amine Associated Receptor 1 (mTAAR1) Agonists.,  58  (12): [PMID:26010728] [10.1021/acs.jmedchem.5b00526]

3. Cichero E, Espinoza S, Tonelli M, Franchini S, Gerasimov AS, Sorbi C, Gainetdinov RR, Brasili L, Fossa P.  (2016)  A homology modelling-driven study leading to the discovery of the first mouse trace amine-associated receptor 5 (TAAR5) antagonists,  7  (2): [10.1039/C5MD00490J]

4. Tonelli M, Espinoza S, Gainetdinov RR, Cichero E..  (2017)  Novel biguanide-based derivatives scouted as TAAR1 agonists: Synthesis, biological evaluation, ADME prediction and molecular docking studies.,  127  [PMID:27823885] [10.1016/j.ejmech.2016.10.058]

5. Chiellini G,Nesi G,Sestito S,Chiarugi S,Runfola M,Espinoza S,Sabatini M,Bellusci L,Laurino A,Cichero E,Gainetdinov RR,Fossa P,Raimondi L,Zucchi R,Rapposelli S.  (2016)  Hit-to-Lead Optimization of Mouse Trace Amine Associated Receptor 1 (mTAAR1) Agonists with a Diphenylmethane-Scaffold: Design, Synthesis, and Biological Study.,  59  (21.0): [PMID:27731647] [10.1021/acs.jmedchem.6b01092]

6. Heffernan MLR, Herman LW, Brown S, Jones PG, Shao L, Hewitt MC, Campbell JE, Dedic N, Hopkins SC, Koblan KS, Xie L..  (2022)  Ulotaront: A TAAR1 Agonist for the Treatment of Schizophrenia.,  13  (1.0): [PMID:35047111] [10.1021/acsmedchemlett.1c00527]

7. Patel BA, D'Amico TL, Blagg BSJ..  (2020)  Natural products and other inhibitors of F₁F_O ATP synthase.,  207  [PMID:32942072] [10.1016/j.ejmech.2020.112779]

Source

Source(1):

• Scientific Literature