ID: ALA487387

Max Phase: Preclinical

Molecular Formula: C19H21NO4

Molecular Weight: 327.38

Molecule Type: Small molecule

Representations

Synonyms (3): (-)-Stepholidine | L-(S)-Stepholidine | L-Stepholidine
Synonyms from Alternative Forms(3):

Canonical SMILES:  COc1cc2c(cc1O)[C@@H]1Cc3ccc(O)c(OC)c3CN1CC2

Standard InChI:  InChI=1S/C19H21NO4/c1-23-18-8-12-5-6-20-10-14-11(3-4-16(21)19(14)24-2)7-15(20)13(12)9-17(18)22/h3-4,8-9,15,21-22H,5-7,10H2,1-2H3/t15-/m0/s1

Standard InChI Key:  JKPISQIIWUONPB-HNNXBMFYSA-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: 327.38

Molecular Weight (Monoisotopic): 327.1471

AlogP: 2.77

#Rotatable Bonds: 2

Polar Surface Area: 62.16

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.81

CX Basic pKa: 4.85

CX LogP: 2.86

CX LogD: 2.85

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.89

Np Likeness Score: 1.43

References

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3. Qian W, Lu W, Sun H, Li Z, Zhu L, Zhao R, Zhang L, Zhou S, Zhou Y, Jiang H, Zhen X, Liu H..  (2012)  Design, synthesis, and pharmacological evaluation of novel tetrahydroprotoberberine derivatives: selective inhibitors of dopamine D₁ receptor.,  20  (15): [PMID:22748706] [10.1016/j.bmc.2012.05.057]

4. 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]

5. 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]

6. Li Z, Huang J, Sun H, Zhou S, Guo L, Zhou Y, Zhen X, Liu H..  (2014)  Design, synthesis and evaluation of benzo[a]thieno[3,2-g]quinolizines as novel l-SPD derivatives possessing dopamine D1, D2 and serotonin 5-HT1A multiple action profiles.,  22  (21): [PMID:25308766] [10.1016/j.bmc.2014.09.024]

7. Gadhiya S, Madapa S, Kurtzman T, Alberts IL, Ramsey S, Pillarsetty NK, Kalidindi T, Harding WW..  (2016)  Tetrahydroprotoberberine alkaloids with dopamine and σ receptor affinity.,  24  (9): [PMID:27032890] [10.1016/j.bmc.2016.03.037]

8. Guo D, Li J, Lin H, Zhou Y, Chen Y, Zhao F, Sun H, Zhang D, Li H, Shoichet BK, Shan L, Zhang W, Xie X, Jiang H, Liu H..  (2016)  Design, Synthesis, and Biological Evaluation of Novel Tetrahydroprotoberberine Derivatives (THPBs) as Selective α1A-Adrenoceptor Antagonists.,  59  (20): [PMID:27709945] [10.1021/acs.jmedchem.6b01217]

9. Madapa S, Gadhiya S, Kurtzman T, Alberts IL, Ramsey S, Reith M, Harding WW..  (2017)  Synthesis and evaluation of C9 alkoxy analogues of (-)-stepholidine as dopamine receptor ligands.,  125  [PMID:27688181] [10.1016/j.ejmech.2016.09.036]

10. Li J, Yan Z, Li H, Shi Q, Ahire V, Zhang S, Nimishetti N, Yang D, Allen TD, Zhang J..  (2021)  The Phytochemical Scoulerine Inhibits Aurora Kinase Activity to Induce Mitotic and Cytokinetic Defects.,  84  (8.0): [PMID:34406008] [10.1021/acs.jnatprod.1c00429]

Source

Source(1):

• Scientific Literature