20S,22S,25S,5alpha-veratramine-14,15,16,17-tetradehydro-3beta,23beta-diol-6-one

ID: ALA3786439

PubChem CID: 127031862

Max Phase: Preclinical

Molecular Formula: C27H39NO3

Molecular Weight: 425.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1c([C@H](C)[C@@H]2NC[C@@H](C)C[C@H]2O)ccc2c1C[C@H]1[C@H]2CC(=O)[C@H]2C[C@@H](O)CC[C@@]21C

Standard InChI:  InChI=1S/C27H39NO3/c1-14-9-25(31)26(28-13-14)16(3)18-5-6-19-20(15(18)2)11-22-21(19)12-24(30)23-10-17(29)7-8-27(22,23)4/h5-6,14,16-17,21-23,25-26,28-29,31H,7-13H2,1-4H3/t14-,16-,17-,21-,22-,23+,25+,26-,27+/m0/s1

Standard InChI Key:  UJPTWYUILIIDCK-YWUKSBHUSA-N

Molfile:  

     RDKit          2D

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    3.2944   -5.4188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3424   -3.9196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182   -5.3344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.1494    0.9005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2355    2.3981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.7432    0.7513    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0841    0.3482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6444    4.2702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7214   -2.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0158   -2.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5623   -0.5358    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2416   -0.4300    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  1  0
  5 13  1  0
  6  7  1  0
  7  8  1  0
  8 14  1  0
  2  9  1  1
  5 10  1  1
  6 11  1  6
 13 12  1  6
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 16 15  1  0
 15 13  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 24 29  1  1
 26 30  1  1
 22 31  1  6
 21 32  1  0
 14 33  1  1
  7 34  2  0
 23 35  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA3786439

   ---

Molecule Features

Natural Product: No

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: 425.61

Molecular Weight (Monoisotopic): 425.2930

AlogP: 3.85

#Rotatable Bonds: 2

Polar Surface Area: 69.56

Molecular Species: BASE

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.80

CX LogP: 3.90

CX LogD: 1.55

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.67

Np Likeness Score: 2.54

References

1. Li Y, Yili A, Li J, Muhamat A, Aisa HA..  (2016)  New isosteroidal alkaloids with tracheal relaxant effect from the bulbs of Fritillaria pallidiflora Schrenk.,  26  (8): [PMID:26965859] [10.1016/j.bmcl.2016.03.001]

Source

Source(1):

• Scientific Literature