ID: ALA2314733

Max Phase: Preclinical

Molecular Formula: C19H19NO4

Molecular Weight: 325.36

Molecule Type: Small molecule

Representations

Synonyms (1): R-(+)-Tetrahydroberberrubine
Synonyms from Alternative Forms(1):

Canonical SMILES:  COc1ccc2c(c1O)CN1CCc3cc4c(cc3[C@H]1C2)OCO4

Standard InChI:  InChI=1S/C19H19NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m1/s1

Standard InChI Key:  PQECCKIOFCWGRJ-OAHLLOKOSA-N

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

Properties

Molecular Weight: 325.36

Molecular Weight (Monoisotopic): 325.1314

AlogP: 2.79

#Rotatable Bonds: 1

Polar Surface Area: 51.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.23

CX Basic pKa: 6.24

CX LogP: 2.94

CX LogD: 2.90

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.87

Np Likeness Score: 1.16

References

1. Ge HX, Zhang J, Chen L, Kou JP, Yu BY..  (2013)  Chemical and microbial semi-synthesis of tetrahydroprotoberberines as inhibitors on tissue factor procoagulant activity.,  21  (1): [PMID:23199480] [10.1016/j.bmc.2012.11.002]

2. Sun H, Zhu L, Yang H, Qian W, Guo L, Zhou S, Gao B, Li Z, Zhou Y, Jiang H, Chen K, Zhen X, Liu H..  (2013)  Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D(1), D(2) and serotonin 5-HT(1A) multi-action profile.,  21  (4): [PMID:23332346] [10.1016/j.bmc.2012.12.016]

Source

Source(1):

• Scientific Literature