4-Deacetyl-4-methoxyl vindoline

ID: ALA4090843

PubChem CID: 137644514

Max Phase: Preclinical

Molecular Formula: C24H32N2O5

Molecular Weight: 428.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@]12C=CCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@H]4[C@@](O)(C(=O)OC)[C@@H]1OC)[C@@H]32

Standard InChI:  InChI=1S/C24H32N2O5/c1-6-22-10-7-12-26-13-11-23(18(22)26)16-9-8-15(29-3)14-17(16)25(2)19(23)24(28,20(22)30-4)21(27)31-5/h7-10,14,18-20,28H,6,11-13H2,1-5H3/t18-,19+,20+,22+,23+,24-/m0/s1

Standard InChI Key:  IHOZUYRKUYKMML-MCIGMTSASA-N

Molfile:  

     RDKit          2D

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   16.5649  -10.0504    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   17.2772   -7.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7859   -9.4846    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4819   -8.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1434   -7.9903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA4090843

   ---

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: 428.53

Molecular Weight (Monoisotopic): 428.2311

AlogP: 1.72

#Rotatable Bonds: 4

Polar Surface Area: 71.47

Molecular Species: BASE

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.89

CX Basic pKa: 8.83

CX LogP: 2.08

CX LogD: 0.64

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: 2.07

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