3-Demethoxycarbonyl-3-(acetylamino)methyl vindoline

ID: ALA4097901

PubChem CID: 44178758

Max Phase: Preclinical

Molecular Formula: C26H35N3O5

Molecular Weight: 469.58

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H35N3O5/c1-6-24-10-7-12-29-13-11-25(21(24)29)19-9-8-18(33-5)14-20(19)28(4)22(25)26(32,15-27-16(2)30)23(24)34-17(3)31/h7-10,14,21-23,32H,6,11-13,15H2,1-5H3,(H,27,30)/t21-,22+,23+,24+,25+,26-/m0/s1

Standard InChI Key:  RJEJNPYXHOZAJG-QHSXUUMZSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA4097901

   [(1R,9R,10S,11R,12R,19R)-10-(acetamidomethyl)-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-11-yl] acetate

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: 469.58

Molecular Weight (Monoisotopic): 469.2577

AlogP: 1.60

#Rotatable Bonds: 5

Polar Surface Area: 91.34

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.81

CX Basic pKa: 8.88

CX LogP: 0.98

CX LogD: -0.52

Aromatic Rings: 1

Heavy Atoms: 34

QED Weighted: 0.50

Np Likeness Score: 1.68

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