ID: ALA455056

Max Phase: Preclinical

Molecular Formula: C32H44O8

Molecular Weight: 556.70

Molecule Type: Small molecule

Representations

Synonyms (1): Cucurbitacin E
Synonyms from Alternative Forms(1):

Canonical SMILES:  CC(=O)OC(C)(C)/C=C/C(=O)[C@](C)(O)[C@H]1[C@H](O)C[C@@]2(C)[C@@H]3CC=C4[C@@H](C=C(O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C

Standard InChI:  InChI=1S/C32H44O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,12-14,19,21-22,25,34-35,39H,11,15-16H2,1-9H3/b13-12+/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1

Standard InChI Key:  NDYMQXYDSVBNLL-MUYMLXPFSA-N

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

Properties

Molecular Weight: 556.70

Molecular Weight (Monoisotopic): 556.3036

AlogP: 4.19

#Rotatable Bonds: 5

Polar Surface Area: 138.20

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.09

CX Basic pKa:

CX LogP: 3.48

CX LogD: 3.47

Aromatic Rings: 0

Heavy Atoms: 40

QED Weighted: 0.26

Np Likeness Score: 3.15

References

1. Nes WD, Patterson GW.  (1981)  Effects of Tetracyclic and Pentacyclic Triterpenoids on Growth of Phytophthora cactorum,  44  (2): [10.1021/np50014a012]

2. Fuller RW, Cardellina JH, Cragg GM, Boyd MR..  (1994)  Cucurbitacins: differential cytotoxicity, dereplication and first isolation from Gonystylus keithii.,  57  (10): [PMID:7807128] [10.1021/np50112a015]

3. Musza LL, Speight P, McElhiney S, Barrow CJ, Gillum AM, Cooper R, Killar LM..  (1994)  Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides.,  57  (11): [PMID:7852999] [10.1021/np50113a004]

4. Madari H, Jacobs RS..  (2004)  An analysis of cytotoxic botanical formulations used in the traditional medicine of ancient Persia as abortifacients.,  67  (8): [PMID:15332833] [10.1021/np049953r]

5. Nakashima S, Matsuda H, Kurume A, Oda Y, Nakamura S, Yamashita M, Yoshikawa M..  (2010)  Cucurbitacin E as a new inhibitor of cofilin phosphorylation in human leukemia U937 cells.,  20  (9): [PMID:20347305] [10.1016/j.bmcl.2010.02.062]

6. Bartalis J, Halaweish FT..  (2011)  In vitro and QSAR studies of cucurbitacins on HepG2 and HSC-T6 liver cell lines.,  19  (8): [PMID:21459003] [10.1016/j.bmc.2011.01.037]

7. PubChem BioAssay data set, 

8. Hall JA, Seedarala S, Rice N, Kopel L, Halaweish F, Blagg BS..  (2015)  Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery.,  78  (4): [PMID:25756299] [10.1021/acs.jnatprod.5b00054]

9. Liu Y, Chen G, Chen X, Chen SX, Gan LS, Yuan T..  (2018)  Colocynthenins A-D, Ring-A seco-Cucurbitane Triterpenoids from the Fruits of Citrullus colocynthis.,  81  (9): [PMID:30183289] [10.1021/acs.jnatprod.8b00461]

10. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of NIH NCI Natural Product Set III,  [10.6019/CHEMBL4296183]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• CO-ADD antimicrobial screening data