ID: ALA489337

Max Phase: Preclinical

Molecular Formula: C17H19NO4

Molecular Weight: 301.34

Molecule Type: Small molecule

Representations

Synonyms (1): Hipppamine
Synonyms from Alternative Forms(1):

Canonical SMILES:  CO[C@H]1C=C2CCN3Cc4cc5c(cc4[C@H]([C@@H]1O)[C@@H]23)OCO5

Standard InChI:  InChI=1S/C17H19NO4/c1-20-14-4-9-2-3-18-7-10-5-12-13(22-8-21-12)6-11(10)15(16(9)18)17(14)19/h4-6,14-17,19H,2-3,7-8H2,1H3/t14-,15-,16+,17+/m0/s1

Standard InChI Key:  GYLFSMMPXXYQAB-MWDXBVQZSA-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: 301.34

Molecular Weight (Monoisotopic): 301.1314

AlogP: 1.40

#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: 13.72

CX Basic pKa: 8.07

CX LogP: 0.81

CX LogD: 0.06

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: 2.39

References

1. Evidente A, Iasiello I, Randazzo G.  (1984)  Hippamine, a Minor Alkaloid From Sternbergia lutea,  47  (6): [10.1021/np50036a041]

2. Dasari R, Banuls LM, Masi M, Pelly SC, Mathieu V, Green IR, van Otterlo WA, Evidente A, Kiss R, Kornienko A..  (2014)  C1,C2-ether derivatives of the Amaryllidaceae alkaloid lycorine: retention of activity of highly lipophilic analogues against cancer cells.,  24  (3): [PMID:24393582] [10.1016/j.bmcl.2013.12.073]

Source

Source(1):

• Scientific Literature