1-(3,4-Dihydroxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-isoquinoline-6,7-diol

ID: ALA19844

Chembl Id: CHEMBL19844

Cas Number: 57231-31-9

PubChem CID: 92716

Max Phase: Preclinical

Molecular Formula: C17H19NO4

Molecular Weight: 301.34

Molecule Type: Small molecule

Names and Identifiers

Synonyms from Alternative Forms(1): Laudanosoline Hydrobromide

Canonical SMILES:  CN1CCc2cc(O)c(O)cc2C1Cc1ccc(O)c(O)c1

Standard InChI:  InChI=1S/C17H19NO4/c1-18-5-4-11-8-16(21)17(22)9-12(11)13(18)6-10-2-3-14(19)15(20)7-10/h2-3,7-9,13,19-22H,4-6H2,1H3

Standard InChI Key:  VHRSWCTVFBWHKE-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA19844

   Laudanosoline

2. Alternative Forms:

   

   ALA19844

   LAUDANOSOLINE HYDROBROMIDE

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: 301.34

Molecular Weight (Monoisotopic): 301.1314

AlogP: 2.28

#Rotatable Bonds: 2

Polar Surface Area: 84.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.15

CX Basic pKa: 7.81

CX LogP: 2.55

CX LogD: 2.23

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.64

Np Likeness Score: 1.23

References

1. Hegde VR, Dai P, Ladislaw C, Patel MG, Puar MS, Pachter JA.  (1997)  D4 dopamine receptor-selective compounds from the Chinese plant Phoebe chekiangensis,  7  (9): [10.1016/S0960-894X(97)00194-7]

2. PubChem BioAssay data set, 

3. Liu Z, Gu S, Zhu X, Liu M, Cao Z, Qiu P, Li S, Liu S, Song G..  (2022)  Discovery and optimization of new 6, 7-dihydroxy-1, 2, 3, 4-tetrahydroisoquinoline derivatives as potent influenza virus PA_N inhibitors.,  227  [PMID:34700269] [10.1016/j.ejmech.2021.113929]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays