Euphoboetirane A

ID: ALA4079791

PubChem CID: 23815273

Max Phase: Preclinical

Molecular Formula: C26H36O7

Molecular Weight: 460.57

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=C1CC[C@H]2[C@@H](/C=C(\C)C(=O)[C@@]3(OC(C)=O)C[C@H](C)[C@H](OC(C)=O)[C@@H]3[C@H]1OC(C)=O)C2(C)C

Standard InChI:  InChI=1S/C26H36O7/c1-13-9-10-19-20(25(19,7)8)11-14(2)24(30)26(33-18(6)29)12-15(3)23(32-17(5)28)21(26)22(13)31-16(4)27/h11,15,19-23H,1,9-10,12H2,2-8H3/b14-11+/t15-,19-,20+,21-,22-,23-,26+/m0/s1

Standard InChI Key:  WFMPZQDIRPRCNA-PNWNLVJFSA-N

Molfile:  

     RDKit          2D

 36 38  0  0  0  0  0  0  0  0999 V2000
    5.1962  -22.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7633  -20.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3588  -20.7600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1759  -20.7553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3798  -20.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3799  -22.5023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1995  -20.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969  -21.9310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8006  -21.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0185  -20.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5314  -21.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0125  -22.1819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7746  -21.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7783  -21.9264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5582  -22.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5522  -20.8510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0342  -21.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5135  -19.7737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0670  -19.7733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8500  -21.5070    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5458  -20.0336    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7142  -21.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564  -22.9579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5783  -22.7163    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0713  -23.2590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3843  -20.3968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5070  -23.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564  -23.1242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7003  -23.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4123  -22.5144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5724  -23.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2638  -24.6613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3820  -23.7935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5672  -20.4019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1541  -19.6968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630  -21.1121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  4  3  1  0
  9  5  1  0
  8  6  1  0
  6  1  1  0
  1 14  1  0
 13  7  2  0
  7  5  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12  8  1  0
 14 15  1  0
 15 17  1  0
 16 13  1  0
 17 16  1  0
  3 17  1  0
 16  3  1  0
  7 18  1  0
  5 19  2  0
 17 20  1  6
 16 21  1  6
 11 22  1  1
 12 23  1  1
  8 24  1  6
  6 25  1  6
  9 26  1  1
  1 27  2  0
 23 28  1  0
 28 29  1  0
 28 30  2  0
 25 31  1  0
 31 32  1  0
 31 33  2  0
 26 34  1  0
 34 35  2  0
 34 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4079791

   [(1R,3E,5R,7S,11R,12R,13S,14S)-1,11-diacetyloxy-3,6,6,14-tetramethyl-10-methylidene-2-oxo-13-tricyclo[10.3.0.05,7]pentadec-3-enyl] 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: 460.57

Molecular Weight (Monoisotopic): 460.2461

AlogP: 3.95

#Rotatable Bonds: 3

Polar Surface Area: 95.97

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.66

CX LogD: 3.66

Aromatic Rings: ┄

Heavy Atoms: 33

QED Weighted: 0.36

Np Likeness Score: 3.06

References

1. Mónico A, Nim S, Duarte N, Rawal MK, Prasad R, Di Pietro A, Ferreira MU..  (2017)  Lathyrol and epoxylathyrol derivatives: Modulation of Cdr1p and Mdr1p drug-efflux transporters of Candida albicans in Saccharomyces cerevisiae model.,  25  (13): [PMID:28479022] [10.1016/j.bmc.2017.04.016]

2. Esposito M, Nim S, Nothias LF, Gallard JF, Rawal MK, Costa J, Roussi F, Prasad R, Di Pietro A, Paolini J, Litaudon M..  (2017)  Evaluation of Jatrophane Esters from Euphorbia spp. as Modulators of Candida albicans Multidrug Transporters.,  80  (2): [PMID:28106996] [10.1021/acs.jnatprod.6b00990]

3. Flores-Giubi E, Geribaldi-Doldán N, Murillo-Carretero M, Castro C, Durán-Patrón R, Macías-Sánchez AJ, Hernández-Galán R..  (2019)  Lathyrane, Premyrsinane, and Related Diterpenes from Euphorbia boetica: Effect on in Vitro Neural Progenitor Cell Proliferation.,  82  (9): [PMID:31507181] [10.1021/acs.jnatprod.9b00343]

Source

Source(1):

• Scientific Literature