3-Demethoxycarbonyl-3-(propionyloxy)methyl vindoline

ID: ALA4099488

Chembl Id: CHEMBL4099488

PubChem CID: 25136711

Max Phase: Preclinical

Molecular Formula: C27H36N2O6

Molecular Weight: 484.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC(=O)OC[C@@]1(O)[C@H](OC(C)=O)[C@]2(CC)C=CCN3CC[C@@]4(c5ccc(OC)cc5N(C)[C@@H]14)[C@@H]32

Standard InChI:  InChI=1S/C27H36N2O6/c1-6-21(31)34-16-27(32)23-26(19-10-9-18(33-5)15-20(19)28(23)4)12-14-29-13-8-11-25(7-2,22(26)29)24(27)35-17(3)30/h8-11,15,22-24,32H,6-7,12-14,16H2,1-5H3/t22-,23+,24+,25+,26+,27-/m0/s1

Standard InChI Key:  DKPOIKMBXFBEEP-IRCHXDIHSA-N

Alternative Forms

1. Parent:

   

   ALA4099488

   [(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 propanoate

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: 484.59

Molecular Weight (Monoisotopic): 484.2573

AlogP: 2.42

#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: 2.41

CX LogD: 0.99

Aromatic Rings: 1

Heavy Atoms: 35

QED Weighted: 0.49

Np Likeness Score: 1.95

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