3-Demethoxycarbonyl-3-(isobutyryloxy)methyl vindoline

ID: ALA4087504

Chembl Id: CHEMBL4087504

PubChem CID: 25136712

Max Phase: Preclinical

Molecular Formula: C28H38N2O6

Molecular Weight: 498.62

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C28H38N2O6/c1-7-26-11-8-13-30-14-12-27(23(26)30)20-10-9-19(34-6)15-21(20)29(5)24(27)28(33,25(26)36-18(4)31)16-35-22(32)17(2)3/h8-11,15,17,23-25,33H,7,12-14,16H2,1-6H3/t23-,24+,25+,26+,27+,28-/m0/s1

Standard InChI Key:  BPGUMMAXTNFZEO-YBMFQFDFSA-N

Alternative Forms

1. Parent:

   

   ALA4087504

   [(1R,9R,10R,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2(7),3,5,13-tetraen-10-yl]methyl 2-methylpropanoate

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: 498.62

Molecular Weight (Monoisotopic): 498.2730

AlogP: 2.67

#Rotatable Bonds: 6

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: 12.41

CX Basic pKa: 8.81

CX LogP: 2.95

CX LogD: 1.53

Aromatic Rings: 1

Heavy Atoms: 36

QED Weighted: 0.47

Np Likeness Score: 1.98

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