4-N-demethylkoumine

ID: ALA4873560

PubChem CID: 164622089

Max Phase: Preclinical

Molecular Formula: C19H20N2O

Molecular Weight: 292.38

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=C[C@@]12CN[C@@H]3C[C@]14C(=Nc1ccccc14)[C@H]1C[C@@H]2[C@@H]3CO1

Standard InChI:  InChI=1S/C19H20N2O/c1-2-18-10-20-15-8-19(18)12-5-3-4-6-14(12)21-17(19)16-7-13(18)11(15)9-22-16/h2-6,11,13,15-16,20H,1,7-10H2/t11-,13+,15+,16+,18-,19-/m0/s1

Standard InChI Key:  CVAPBADJBVUJQA-ALRJNDEISA-N

Molfile:  

 
     RDKit          2D

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    7.3374  -32.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0475  -32.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3374  -30.9740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0455  -31.3974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7629  -30.9919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7743  -30.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0617  -29.7471    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3422  -30.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6230  -32.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180  -31.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8365  -32.4765    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3438  -31.8127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8311  -31.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4932  -30.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771  -30.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1913  -30.9810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5276  -31.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6140  -30.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4919  -29.7591    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7591  -31.8053    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6109  -29.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4094  -31.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1970  -31.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2184  -32.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3291  -33.5168    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5590  -30.7774    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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  9  1  1  0
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  3 18  1  6
  6 19  1  6
  4 20  1  6
 18 21  2  0
 10 22  1  1
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  5 23  1  0
  1 24  1  0
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  1 25  1  6
  5 26  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4873560

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 292.38

Molecular Weight (Monoisotopic): 292.1576

AlogP: 2.59

#Rotatable Bonds: 1

Polar Surface Area: 33.62

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.78

CX LogP: 2.34

CX LogD: 0.01

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.81

Np Likeness Score: 2.35

References

1. Jin P, Zhan G, Zheng G, Liu J, Peng X, Huang L, Gao B, Yuan X, Yao G..  (2021)  Gelstriamine A, a Triamino Monoterpene Indole Alkaloid with a Caged 6/5/7/6/6/5 Scaffold and Analgesic Alkaloids from Gelsemium elegans Stems.,  84  (4.0): [PMID:33826318] [10.1021/acs.jnatprod.1c00062]

Source

Source(1):

• Scientific Literature