ID: ALA61006

Max Phase: Approved

First Approval: 1958

Molecular Formula: C9H13NO

Molecular Weight: 151.21

Molecule Type: Small molecule

Representations

Synonyms (7): Fansia | Norephedrine | Phenylfenesin | Phenylpropanolamine | Propadrine | Rinexin | NSC-9920
Synonyms from Alternative Forms(7):

Canonical SMILES:  CC(N)C(O)c1ccccc1

Standard InChI:  InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3

Standard InChI Key:  DLNKOYKMWOXYQA-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: Yes

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 151.21

Molecular Weight (Monoisotopic): 151.0997

AlogP: 1.07

#Rotatable Bonds: 2

Polar Surface Area: 46.25

Molecular Species: BASE

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.90

CX Basic pKa: 9.37

CX LogP: 0.89

CX LogD: -1.05

Aromatic Rings: 1

Heavy Atoms: 11

QED Weighted: 0.66

Np Likeness Score: 0.57

References

1. Altenbach RJ, Khilevich A, Kolasa T, Rohde JJ, Bhatia PA, Patel MV, Searle XB, Yang F, Bunnelle WH, Tietje K, Bayburt EK, Carroll WA, Meyer MD, Henry R, Buckner SA, Kuk J, Daza AV, Milicic IV, Cain JC, Kang CH, Ireland LM, Carr TL, Miller TR, Hancock AA, Nakane M, Esbenshade TA, Brune ME, O'Neill AB, Gauvin DM, Katwala SP, Holladay MW, Brioni JD, Sullivan JP..  (2004)  Synthesis and structure-activity studies on N-[5-(1H-imidazol-4-yl)-5,6,7,8-tetrahydro-1-naphthalenyl]methanesulfonamide, an imidazole-containing alpha(1A)-adrenoceptor agonist.,  47  (12): [PMID:15163201] [10.1021/jm030551a]

2. Carroll WA, Altenbach RJ, Buckner SA, Brioni JD, Brune ME, Kolasa T, Meyer MD, Sullivan JP.  (2004)  In Vitro and In Vivo Characterization of Alpha-1A Selective Agonists and Their Utility for Stress Incontience,  13  (3): [10.1007/s00044-004-0020-z]

3. Miller DD, Hsu FL, Salman KN, Patil PN..  (1976)  Stereochemical studies of adrenergic drugs. Diastereomeric 2-amino-1-phenylcyclobutanols.,  19  (1): [PMID:1246042] [10.1021/jm00223a036]

4. WHO Anatomical Therapeutic Chemical Classification, 

5. Unpublished dataset, 

6. Unpublished dataset, 

7. 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(4):

• Scientific Literature
• Clinical Candidates
• Withdrawn Drugs
• WHO Anatomical Therapeutic Chemical Classification