11-methoxy-19-(R)-hydroxygelselegine

ID: ALA4873355

PubChem CID: 11090753

Max Phase: Preclinical

Molecular Formula: C21H28N2O6

Molecular Weight: 404.46

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)N(OC)C(=O)[C@@]21C[C@@H]2N[C@](CO)([C@@H](C)O)[C@@H]3C[C@H]1OC[C@H]23

Standard InChI:  InChI=1S/C21H28N2O6/c1-11(25)21(10-24)15-7-18-20(8-16(22-21)13(15)9-29-18)14-5-4-12(27-2)6-17(14)23(28-3)19(20)26/h4-6,11,13,15-16,18,22,24-25H,7-10H2,1-3H3/t11-,13+,15-,16+,18-,20+,21-/m1/s1

Standard InChI Key:  GWYGPYIOBSALOZ-DMLIBQJSSA-N

Molfile:  

 
     RDKit          2D

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    9.2386  -17.6156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2375  -18.4752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0418  -16.7680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.4314  -16.4178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9933  -15.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9554  -16.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2450  -16.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4211  -17.5361    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5705  -16.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8557  -17.1736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2404  -15.8746    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6943  -15.8838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3908  -16.6092    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4918  -18.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9804  -18.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9363  -16.5378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5431  -17.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7271  -17.6166    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  6
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  6  7  1  0
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  8  9  1  0
  9 10  1  0
  4 10  1  0
 11 12  2  0
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 14 15  1  0
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  8 17  1  0
 17 18  1  0
  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
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 22 26  1  6
 21 27  1  6
 24 28  1  1
  3 29  1  0
  1 30  1  0
 15 31  1  0
 31 32  1  0
  1 33  1  6
  7  4  1  0
  5 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4873355

   (1R,2S,4S,6R,7R,8S)-6-[(1R)-1-hydroxyethyl]-6-(hydroxymethyl)-1',6'-dimethoxyspiro[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: 404.46

Molecular Weight (Monoisotopic): 404.1947

AlogP: 0.35

#Rotatable Bonds: 4

Polar Surface Area: 100.49

Molecular Species: BASE

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.30

CX LogP: -0.35

CX LogD: -3.09

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.67

Np Likeness Score: 1.93

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