4-(2-Amino-1-hydroxy-ethyl)-phenol

ID: ALA53929

Chembl Id: CHEMBL53929

Cas Number: 104-14-3

PubChem CID: 4581

Max Phase: Phase

Molecular Formula: C8H11NO2

Molecular Weight: 153.18

Molecule Type: Small molecule

Names and Identifiers

Synonyms: ND 50 | ND-50 | NSC-757399 | octopamine|Norsynephrine|104-14-3|4-(2-Amino-1-hydroxyethyl)phenol|Norsympatol|Norsympathol|Norden|Norphen|Analet|octopaminum|Octapamine|Octopamina|p-Norsynephrin|Octopamine [INN]|Paraoxyphenyl aminoethanol|ND 50|1-(p-Hydroxyphenyl)-2-aminoethanol|Octopaminum [Latin]|Octopamin|WIN 5512|Octopaminum [INN-Latin]|p-Hydroxyphenylethanolamine|beta-hydroxytyramine|Octopamina [INN-Spanish]|alpha-(Aminoethyl)-4-hydroxybenzenemethanol|alpha-(Aminomethyl)-p-hydroxybenzyl alcohoShow More⌵

Canonical SMILES:  NCC(O)c1ccc(O)cc1

Standard InChI:  InChI=1S/C8H11NO2/c9-5-8(11)6-1-3-7(10)4-2-6/h1-4,8,10-11H,5,9H2

Standard InChI Key:  QHGUCRYDKWKLMG-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA53929

   OCTOPAMINE

2. Alternative Forms:

   

   ALA53929

   (±)-Octopamine 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: 153.18

Molecular Weight (Monoisotopic): 153.0790

AlogP: 0.38

#Rotatable Bonds: 2

Polar Surface Area: 66.48

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.64

CX Basic pKa: 8.98

CX LogP: -0.32

CX LogD: -1.56

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.58

Np Likeness Score: 0.89

References

1. Nathanson JA, Kaugars G..  (1989)  A probe for octopamine receptors: synthesis of 2-[(4-azido-2,6-diethylphenyl)imino]imidazolidine and its tritiated derivative, a potent reversible-irreversible activator of octopamine-sensitive adenylate cyclase.,  32  (8): [PMID:2502628] [10.1021/jm00128a022]

2. Leclerc G, Bizec JC, Bieth N, Schwartz J..  (1980)  Synthesis and structure-activity relationships among alpha-adrenergic receptor agonists of the phenylethanolamine type.,  23  (7): [PMID:6105214] [10.1021/jm00181a008]

3. Petrascheck M, Ye X, Buck LB..  (2007)  An antidepressant that extends lifespan in adult Caenorhabditis elegans.,  450  (7169): [PMID:18033297] [10.1038/nature05991]

4. Bard B, Carrupt PA, Martel S..  (2009)  Lipophilicity of basic drugs measured by hydrophilic interaction chromatography.,  52  (10): [PMID:19397318] [10.1021/jm9003945]

5. PubChem BioAssay data set, 

6. PubChem BioAssay data set, 

7. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

8. HIRASHIMA A, PAN C, KATAFUCHI Y, TANIGUCHI E, ETO M.  (1996)  Synthesis and Octopaminergic-Agonist Activity of 2-(Arylimino)oxazolidines and 2-(Substituted Benzylamino)-2-oxazolines,  21  (4): [10.1584/jpestics.21.419]

9. PubChem BioAssay data set, 

10. Dunn WJ, Wold S..  (1978)  Structure-activity study of beta-adrenergic agents using the SIMCA method of pattern recognition.,  21  (9): [PMID:31486] [10.1021/jm00207a015]

11. PubChem BioAssay data set, 

12. WHO Anatomical Therapeutic Chemical Classification, 

13. Glennon RA..  (2017)  The 2014 Philip S. Portoghese Medicinal Chemistry Lectureship: The "Phenylalkylaminome" with a Focus on Selected Drugs of Abuse.,  60  (7): [PMID:28244748] [10.1021/acs.jmedchem.7b00085]

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. Jensen O, Brockmöller J, Dücker C..  (2021)  Identification of Novel High-Affinity Substrates of OCT1 Using Machine Learning-Guided Virtual Screening and Experimental Validation.,  64  (5.0): [PMID:33606526] [10.1021/acs.jmedchem.0c02047]

Source

Source(6):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• WHO Anatomical Therapeutic Chemical Classification
• IMI-CARE SARS-CoV-2 Data
• Fraunhofer HDAC6