4-Deacetyl-4-propionyloxy-6,7-dihydrovindoline

ID: ALA4098564

PubChem CID: 137662283

Max Phase: Preclinical

Molecular Formula: C26H36N2O6

Molecular Weight: 472.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)O[C@@H]1[C@]2(CC)CCCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@H]4[C@@]1(O)C(=O)OC)[C@@H]32

Standard InChI:  InChI=1S/C26H36N2O6/c1-6-19(29)34-22-24(7-2)11-8-13-28-14-12-25(20(24)28)17-10-9-16(32-4)15-18(17)27(3)21(25)26(22,31)23(30)33-5/h9-10,15,20-22,31H,6-8,11-14H2,1-5H3/t20-,21+,22+,24+,25+,26-/m0/s1

Standard InChI Key:  WKFWBHUZBYPPCZ-IRDNYISJSA-N

Molfile:  

     RDKit          2D

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    6.7303   -6.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7805   -8.7392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4304   -5.2674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7760   -5.7903    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4809   -8.4458    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8977   -5.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2130   -7.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -6.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7017   -7.8800    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3977   -7.1330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4270   -8.7445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9093   -7.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6023   -6.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -6.3855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0432   -8.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4 23  1  0
  6 25  1  0
 17 12  2  0
 27 21  1  0
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  2  9  1  0
 16 31  1  0
 26  1  2  0
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 30 20  1  0
 33 29  2  0
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 22 32  1  0
  3 16  1  0
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 33  6  1  0
  8 10  1  0
 29 26  1  0
 16 17  1  6
 27  5  1  6
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 14 33  1  0
 21 18  1  0
  7 13  1  0
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  8 24  1  1
 17 30  1  0
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 15 14  2  0
 27 22  1  0
 31 22  1  0
  1 15  1  0
 10 27  1  0
 31  7  1  1
 13 34  2  0
 13 35  1  0
 35 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098564

   ---

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: 472.58

Molecular Weight (Monoisotopic): 472.2573

AlogP: 2.26

#Rotatable Bonds: 5

Polar Surface Area: 88.54

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.91

CX Basic pKa: 9.73

CX LogP: 2.53

CX LogD: 0.45

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.65

Np Likeness Score: 1.63

References

1. Xiao C, Tian Y, Lei M, Chen F, Gan X, Yao X, Shen X, Chen J, Hu L..  (2017)  Synthesis and glucose-stimulate insulin secretion (GSIS) evaluation of vindoline derivatives.,  27  (5): [PMID:28162858] [10.1016/j.bmcl.2016.09.064]

Source

Source(1):

• Scientific Literature