Gelselegine

ID: ALA4870600

PubChem CID: 14781525

Max Phase: Preclinical

Molecular Formula: C20H26N2O4

Molecular Weight: 358.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@]1(CO)N[C@H]2C[C@@]3(C(=O)N(OC)c4ccccc43)[C@H]3C[C@@H]1[C@@H]2CO3

Standard InChI:  InChI=1S/C20H26N2O4/c1-3-19(11-23)14-8-17-20(9-15(21-19)12(14)10-26-17)13-6-4-5-7-16(13)22(25-2)18(20)24/h4-7,12,14-15,17,21,23H,3,8-11H2,1-2H3/t12-,14+,15-,17+,19-,20-/m0/s1

Standard InChI Key:  ZREVWZNVVDYUMA-SJBBDNDTSA-N

Molfile:  

 
     RDKit          2D

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   48.7351  -10.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.7340  -11.6645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5374   -9.9540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.3280   -9.1568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.2799   -8.6974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.4555   -8.6171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   45.1328  -10.9193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   45.8687  -10.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7316   -9.7388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.5535  -10.3354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   44.4886   -8.9162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.6640   -8.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.2911   -9.6864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.7382  -10.3738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.0016  -11.7363    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   44.2319  -12.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.6037  -10.9211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   46.9587  -10.6912    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   48.4508   -9.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.7415   -9.9220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.9186  -10.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   49.0686  -10.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   48.3551  -10.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   47.7370   -9.0612    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   49.1884   -9.0703    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   49.8881   -9.7945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   47.9896  -12.0894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   49.4758  -12.0922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 10  1  0
 11 12  2  0
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 16 11  1  0
  8 17  1  0
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  9 19  2  0
  4 20  1  1
 21 22  1  0
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  2 24  1  0
 24 21  1  0
 24 25  1  0
 25  4  1  0
 22 26  1  6
 21 27  1  6
 24 28  1  1
  3 29  1  0
  1 30  1  0
 22  5  1  0
  4  7  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4870600

   (1R,2S,4S,6R,7R,8S)-6-ethyl-6-(hydroxymethyl)-1'-methoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one

Molecule Features

Natural Product: Yes

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: 358.44

Molecular Weight (Monoisotopic): 358.1893

AlogP: 1.37

#Rotatable Bonds: 3

Polar Surface Area: 71.03

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.83

CX LogP: 0.96

CX LogD: -2.06

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.85

Np Likeness Score: 2.07

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