3-(4-{[(4-{[(1R,2S,3R,6R,8R,13S,14R,15R,16S,17R)-15,16-dihydroxy-17-(methoxycarbonyl)-9,13-dimethyl-3-[(3-methylbut-2-enoyl)oxy]-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.0^{1,6}.0^{2,17}.0^{8,13}]nonadec-9-en-10-yl]oxy}-4-oxobutanoyl)oxy]methyl}phenoxymethyl)-4-phenyl-1,2,5-oxadiazol-2-ium-2-olate

ID: ALA3342212

PubChem CID: 118716334

Max Phase: Preclinical

Molecular Formula: C46H48N2O17

Molecular Weight: 900.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)[C@]12OC[C@]34[C@H]([C@@H](O)[C@@H]1O)[C@@]1(C)CC(=O)C(OC(=O)CCC(=O)OCc5ccc(OCc6c(-c7ccccc7)no[n+]6[O-])cc5)=C(C)[C@@H]1C[C@H]3OC(=O)[C@H](OC(=O)C=C(C)C)[C@@H]24

Standard InChI:  InChI=1S/C46H48N2O17/c1-23(2)17-34(52)64-38-40-45-22-61-46(40,43(56)58-5)41(54)36(53)39(45)44(4)19-30(49)37(24(3)28(44)18-31(45)62-42(38)55)63-33(51)16-15-32(50)60-20-25-11-13-27(14-12-25)59-21-29-35(47-65-48(29)57)26-9-7-6-8-10-26/h6-14,17,28,31,36,38-41,53-54H,15-16,18-22H2,1-5H3/t28-,31+,36+,38+,39+,40+,41-,44-,45+,46+/m0/s1

Standard InChI Key:  ZOZMOEPGFWRRHO-MPPVNBQVSA-N

Molfile:  

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M  CHG  2  62   1  69  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3342212

   ---

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: 900.89

Molecular Weight (Monoisotopic): 900.2953

AlogP: 2.89

#Rotatable Bonds: 13

Polar Surface Area: 260.46

Molecular Species: NEUTRAL

HBA: 18

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.75

CX Basic pKa: ┄

CX LogP: 1.32

CX LogD: 1.32

Aromatic Rings: 3

Heavy Atoms: 65

QED Weighted: 0.11

Np Likeness Score: 1.83

References

1. Tang W, Xie J, Xu S, Lv H, Lin M, Yuan S, Bai J, Hou Q, Yu S..  (2014)  Novel nitric oxide-releasing derivatives of brusatol as anti-inflammatory agents: design, synthesis, biological evaluation, and nitric oxide release studies.,  57  (18): [PMID:25179783] [10.1021/jm5007534]

Source

Source(1):

• Scientific Literature