ID: ALA302501

Max Phase: Preclinical

Molecular Formula: C19H22N2O

Molecular Weight: 294.40

Molecule Type: Small molecule

Representations

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

Canonical SMILES:  CC[C@]12CCCn3ccc(c31)-c1ccccc1NC(=O)CC2

Standard InChI:  InChI=1S/C19H22N2O/c1-2-19-10-5-12-21-13-9-15(18(19)21)14-6-3-4-7-16(14)20-17(22)8-11-19/h3-4,6-7,9,13H,2,5,8,10-12H2,1H3,(H,20,22)/t19-/m1/s1

Standard InChI Key:  VLQAFTDOIRUYSZ-LJQANCHMSA-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: 294.40

Molecular Weight (Monoisotopic): 294.1732

AlogP: 4.33

#Rotatable Bonds: 1

Polar Surface Area: 34.03

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.43

CX Basic pKa:

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: 0.76

References

1. David B, Sevenet T, Thoison O, Awang K, Pais M, Wright M, Guenard D.  (1997)  Hemisynthesis of rhazinilam analogues: structure - activity relationships on tubulin-microtubule system,  7  (17): [10.1016/S0960-894X(97)00391-0]

2. David B, Sevenet T, Thoison O, Awang K, Pais M, Wright M, Guenard D.  (1997)  Hemisynthesis of rhazinilam analogues: structure - activity relationships on tubulin-microtubule system,  7  (17): [10.1016/S0960-894X(97)00391-0]

3. Subramaniam G, Hiraku O, Hayashi M, Koyano T, Komiyama K, Kam TS..  (2007)  Biologically active aspidofractinine, rhazinilam, akuammiline, and vincorine alkaloids from Kopsia.,  70  (11): [PMID:17939738] [10.1021/np0703747]

4. Wu Y, Suehiro M, Kitajima M, Matsuzaki T, Hashimoto S, Nagaoka M, Zhang R, Takayama H..  (2009)  Rhazinilam and quebrachamine derivatives from Yunnan Kopsia arborea.,  72  (2): [PMID:19133778] [10.1021/np800489e]

5. Zeng T, Wu XY, Yang SX, Lai WC, Shi SD, Zou Q, Liu Y, Li LM..  (2017)  Monoterpenoid Indole Alkaloids from Kopsia officinalis and the Immunosuppressive Activity of Rhazinilam.,  80  (4): [PMID:28218521] [10.1021/acs.jnatprod.6b00697]

Source

Source(1):

• Scientific Literature