ID: ALA401798

Max Phase: Preclinical

Molecular Formula: C17H15NO2

Molecular Weight: 265.31

Molecule Type: Small molecule

Representations

Synonyms (2): (-)-Anonaine | Anonaine
Synonyms from Alternative Forms(2):

Canonical SMILES:  c1ccc2c(c1)C[C@H]1NCCc3cc4c(c-2c31)OCO4

Standard InChI:  InChI=1S/C17H15NO2/c1-2-4-12-10(3-1)7-13-15-11(5-6-18-13)8-14-17(16(12)15)20-9-19-14/h1-4,8,13,18H,5-7,9H2/t13-/m1/s1

Standard InChI Key:  VZTUKBKUWSHDFM-CYBMUJFWSA-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: 265.31

Molecular Weight (Monoisotopic): 265.1103

AlogP: 2.83

#Rotatable Bonds: 0

Polar Surface Area: 30.49

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 9.20

CX LogP: 2.94

CX LogD: 1.15

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.79

Np Likeness Score: 1.73

References

1. Miski M, Xing Shen, Cooper R, Gillum AM, Fisher DK, Miller RW, Higgins TJ.  (1995)  Aporphine alkaloids, CD45 protein tyrosine phosphatase inhibitors, from Rollinia ulei,  5  (14): [10.1016/0960-894X(95)00250-W]

2. Zhang A, Zhang Y, Branfman AR, Baldessarini RJ, Neumeyer JL..  (2007)  Advances in development of dopaminergic aporphinoids.,  50  (2): [PMID:17228858] [10.1021/jm060959i]

3. Chen CY, Chang FR, Shih YC, Hsieh TJ, Chia YC, Tseng HY, Chen HC, Chen SJ, Hsu MC, Wu YC..  (2000)  Cytotoxic constituents of Polyalthia longifolia var. pendula.,  63  (11): [PMID:11087586] [10.1021/np000176e]

4. Protais P, Arbaoui J, Bakkali EH, Bermejo A, Cortes D..  (1995)  Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes.,  58  (10): [PMID:8676127] [10.1021/np50124a001]

5. Correché ER, Andujar SA, Kurdelas RR, Gómez Lechón MJ, Freile ML, Enriz RD..  (2008)  Antioxidant and cytotoxic activities of canadine: biological effects and structural aspects.,  16  (7): [PMID:18295494] [10.1016/j.bmc.2008.02.015]

6. Queiroz EF, Roblot F, Cavé A, Paulo MQ, Fournet A..  (1996)  Pessoine and spinosine, two catecholic berbines from Annona spinescens.,  59  (4): [PMID:8699188] [10.1021/np960223w]

7. Likhitwitayawuid K, Angerhofer CK, Chai H, Pezzuto JM, Cordell GA, Ruangrungsi N..  (1993)  Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.,  56  (9): [PMID:8254346] [10.1021/np50099a005]

8. Liu YP, Wang TW, Xie Z, Bian Y, Liu YY, Guan RQ, Liu ZY, Qiang L, Chen GY, Fu YH..  (2021)  Artapilosines A and B, Unusual Phenanthrene Derivatives Related to Aporphine Alkaloids from Artabotrys pilosus.,  84  (12.0): [PMID:34812640] [10.1021/acs.jnatprod.1c00896]

Source

Source(1):

• Scientific Literature