(1R,2S,3R,6R,8R,13S,14R,15R,16S,17R)-10,15,16-trihydroxy-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-ene-17-carboxylic acid

ID: ALA3342216

PubChem CID: 10391474

Max Phase: Preclinical

Molecular Formula: C25H30O11

Molecular Weight: 506.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CC(=O)O[C@H]1C(=O)O[C@@H]2C[C@H]3C(C)=C(O)C(=O)C[C@]3(C)[C@H]3[C@@H](O)[C@H](O)[C@]4(C(=O)O)OC[C@]32[C@@H]14

Standard InChI:  InChI=1S/C25H30O11/c1-9(2)5-14(27)36-17-19-24-8-34-25(19,22(32)33)20(30)16(29)18(24)23(4)7-12(26)15(28)10(3)11(23)6-13(24)35-21(17)31/h5,11,13,16-20,28-30H,6-8H2,1-4H3,(H,32,33)/t11-,13+,16+,17+,18+,19+,20-,23-,24+,25+/m0/s1

Standard InChI Key:  RIYGDELXURVOBZ-HVCNMUSHSA-N

Molfile:  

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M  END

Alternative Forms

1. Parent:

   

   ALA3342216

   (1R,2S,3R,6R,8R,13S,14R,15R,16S,17R)-10,15,16-trihydroxy-9,13-dimethyl-3-(3-methylbut-2-enoyloxy)-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylic acid

Molecule Features

Natural Product: Yes

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: 506.50

Molecular Weight (Monoisotopic): 506.1788

AlogP: 0.43

#Rotatable Bonds: 3

Polar Surface Area: 176.89

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.46

CX Basic pKa: ┄

CX LogP: 0.09

CX LogD: -3.31

Aromatic Rings: ┄

Heavy Atoms: 36

QED Weighted: 0.31

Np Likeness Score: 3.67

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