(R)-1-(4-hydroxybenzyl)-1,2,3,4-tetrahydroisoquinoline-6,7-diol

ID: ALA501778

Chembl Id: CHEMBL501778

Cas Number: 106032-53-5

PubChem CID: 440988

Max Phase: Preclinical

Molecular Formula: C16H17NO3

Molecular Weight: 271.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Oc1ccc(C[C@H]2NCCc3cc(O)c(O)cc32)cc1

Standard InChI:  InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2/t14-/m1/s1

Standard InChI Key:  WZRCQWQRFZITDX-CQSZACIVSA-N

Alternative Forms

1. Parent:

   

   ALA501778

   (+)-HIGENAMINE

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: 271.32

Molecular Weight (Monoisotopic): 271.1208

AlogP: 2.23

#Rotatable Bonds: 2

Polar Surface Area: 72.72

Molecular Species: BASE

HBA: 4

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.56

CX Basic pKa: 9.47

CX LogP: 2.36

CX LogD: 1.41

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.63

Np Likeness Score: 1.38

References

1. Pyo MK, Lee DH, Kim DH, Lee JH, Moon JC, Chang KC, Yun-Choi HS..  (2008)  Enantioselective synthesis of (R)-(+)- and (S)-(-)-higenamine and their analogues with effects on platelet aggregation and experimental animal model of disseminated intravascular coagulation.,  18  (14): [PMID:18556200] [10.1016/j.bmcl.2008.05.094]

2. Kato E, Kimura S, Kawabata J..  (2017)  Ability of higenamine and related compounds to enhance glucose uptake in L6 cells.,  25  (24): [PMID:29066136] [10.1016/j.bmc.2017.10.011]

3. Bernhard Ellinger, Denisa Bojkova, Andrea Zaliani, Jindrich Cinatl, Carsten Claussen, Sandra Westhaus, Jeanette Reinshagen, Maria Kuzikov, Markus Wolf, Gerd Geisslinger, Philip Gribbon, Sandra Ciesek.  (2020)  Identification of inhibitors of SARS-CoV-2 in-vitro cellular toxicity in human (Caco-2) cells using a large scale drug repurposing collection,  [10.21203/rs.3.rs-23951/v1]

4. Maria Kuzikov, Elisa Costanzi, Jeanette Reinshagen, Francesca Esposito, Laura Vangeel, Markus Wolf, Bernhard Ellinger, Carsten Claussen, Gerd Geisslinger, Angela Corona, Daniela Iaconis, Carmine Talarico, Candida Manelfi, Rolando Cannalire, Giulia Rossetti, Jonas Gossen, Simone Albani, Francesco Musiani, Katja Herzog, Yang Ye, Barbara Giabbai, Nicola Demitri, Dirk Jochmans, Steven De Jonghe, Jasper Rymenants, Vincenzo Summa, Enzo Tramontano, Andrea R. Beccari, Pieter Leyssen, Paola Storici, Johan Neyts, Philip Gribbon, and Andrea Zaliani.  (2020)  Identification of inhibitors of SARS-Cov2 M-Pro enzymatic activity using a small molecule repurposing screen,  [10.6019/CHEMBL4495564]

5. Andrea Zaliani, Laura Vangeel, Jeanette Reinshagen, Daniela Iaconis, Maria Kuzikov, Oliver Keminer, Markus Wolf, Bernhard Ellinger, Francesca Esposito, Angela Corona, Enzo Tramontano, Candida Manelfi, Katja Herzog, Dirk Jochmans, Steven De Jonghe, Winston Chiu, Thibault Francken, Joost Schepers, Caroline Collard, Kayvan Abbasi, Carsten Claussen , Vincenzo Summa, Andrea R. Beccari, Johan Neyts, Philip Gribbon and Pieter Leyssen.  (2020)  Cytopathic SARS-Cov2 screening on VERO-E6 cells in a large repurposing effort,  [10.6019/CHEMBL4495565]

Source

Source(2):

• Scientific Literature
• SARS-CoV-2 Screening Data 2020-21