6a-ethyl-(6aR)-4,5,6,6a,7,8,9,10-octahydrobenzo[2,3]azonino[6,5,4-hi]indolizin-9-one

ID: ALA302501

PubChem CID: 11312435

Max Phase: Preclinical

Molecular Formula: C19H22N2O

Molecular Weight: 294.40

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Rhazinilam | Rhazinilam|CHEMBL302501|SCHEMBL4908273|Q18394240|(12R)-12-ethyl-8,16-diazatetracyclo[10.6.1.0?,?.0??,??]nonadeca-1(19),2,4,6,17-pentaen-9-one|(12R)-12-ethyl-8,16-diazatetracyclo[10.6.1.02,7.016,19]nonadeca-1(19),2,4,6,17-pentaen-9-one

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

Molfile:  

     RDKit          2D

 22 25  0  0  1  0  0  0  0  0999 V2000
    2.9792   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -2.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -1.6292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -2.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -4.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -1.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -4.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -1.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -4.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1167   -4.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1125   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  1  1  0
  6  7  1  0
  7  5  1  0
  8  3  2  0
  9  2  1  0
 10  6  1  0
 11  9  1  0
 12 10  2  0
 13 11  1  0
 14  4  1  0
 15  9  1  0
 16  5  2  0
  9 17  1  1
 18  7  2  0
 19 15  1  0
 20 17  1  0
 21 16  1  0
 22 21  2  0
  8  4  1  0
 18 22  1  0
 14 19  1  0
 10 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA302501

   RHAZINILAM

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

Calculated 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: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

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