11-Hydroxyhumantenine N4-Oxide

ID: ALA4873044

PubChem CID: 164619924

Max Phase: Preclinical

Molecular Formula: C21H26N2O5

Molecular Weight: 386.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\C[N@+](C)([O-])[C@H]2C[C@@]3(C(=O)N(OC)c4cc(O)ccc43)[C@H]3C[C@@H]1[C@@H]2CO3

Standard InChI:  InChI=1S/C21H26N2O5/c1-4-12-10-23(2,26)18-9-21(19-8-14(12)15(18)11-28-19)16-6-5-13(24)7-17(16)22(27-3)20(21)25/h4-7,14-15,18-19,24H,8-11H2,1-3H3/b12-4+/t14-,15-,18-,19+,21-,23-/m0/s1

Standard InChI Key:  VBBVZFKXDVGVIU-KLAWQQEOSA-N

Molfile:  

 
     RDKit          2D

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   33.7917   -2.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5835   -1.2470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9982   -2.8410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.4177   -2.0123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4177   -2.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   34.9982   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.7080   -1.5935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5336   -0.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7092   -0.7058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.6994   -2.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3859   -3.0087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.1222   -2.6386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9904   -1.8302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8099   -2.4236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1877   -1.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7499   -1.0077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9254   -1.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5499   -1.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9947   -2.4662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2600   -3.8257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4856   -4.1185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8576   -3.0105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2151   -2.7818    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   36.4415   -1.1656    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   37.1580   -1.5852    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   34.2601   -3.2672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1575   -3.2643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1575   -4.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9937   -3.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.9892   -1.1519    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   29.6906   -1.8190    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  1  0
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  8  9  1  0
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  4 11  1  0
 11  1  1  0
 14  2  1  6
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 12 13  1  0
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  1 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 12 21  1  0
 21 22  1  0
 13 23  2  0
  1 24  1  1
  8 25  1  6
  4 26  1  1
  3 27  1  1
  5 28  2  0
 28 29  1  0
  3 30  1  0
  7 31  1  6
 19 32  1  0
 10  1  1  0
  7  2  1  0
M  CHG  2   3   1  30  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4873044

   ---

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: 386.45

Molecular Weight (Monoisotopic): 386.1842

AlogP: 2.24

#Rotatable Bonds: 1

Polar Surface Area: 82.06

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.94

CX Basic pKa: 3.67

CX LogP: 0.59

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: 2.92

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