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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H44O7
Molecular Weight 516.6662
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CUCURBITACIN D

SMILES

[H][C@@]1([C@H](O)C[C@@]2(C)[C@]3([H])CC=C4[C@@]([H])(C[C@H](O)C(=O)C4(C)C)[C@]3(C)C(=O)C[C@]12C)[C@@](C)(O)C(=O)\C=C\C(C)(C)O

InChI

InChIKey=SRPHMISUTWFFKJ-QJNWWGCFSA-N
InChI=1S/C30H44O7/c1-25(2,36)12-11-21(33)30(8,37)23-19(32)14-27(5)20-10-9-16-17(13-18(31)24(35)26(16,3)4)29(20,7)22(34)15-28(23,27)6/h9,11-12,17-20,23,31-32,36-37H,10,13-15H2,1-8H3/b12-11+/t17-,18+,19-,20+,23+,27+,28-,29+,30+/m1/s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27824155

Cucurbitacin D is a plant steroid with anticancer activity. Cucurbitacin D treatment of cervical cancer cells arrested the cell cycle in G1/S phase, inhibited constitutive expression of E6, Cyclin D1, CDK4, pRb, and Rb and induced the protein levels of p21 and p27. Cucurbitacin D also inhibited phosphorylation of STAT3 at Ser727 and Tyr705 residues as well as its downstream target genes c-Myc, and MMP9. In addition, Cucurbitacin D could be used as a useful compound to treat adriamycin-resistant patients with breast carcinoma.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

athymic nude mice: 1 mg/kg body weight injected intra-tumorally 3 days a week
Route of Administration: Other
To determine the effect of Cucurbitacin D on proliferation of cervical cancer cells (CaSki and SiHa), MTS assay was performed. Cucurbitacin D treatment (0.05–1 μM) dose-dependently inhibited viability of cervical cancer cells. IC50 of Cucurbitacin D was 400 nM and 250 nM in CaSki and SiHa cells, respectively, after 72 hrs treatment. 0.5 μM of Cucurbitacin D effectively inhibited invasion of both CaSki and SiHa cells when compared with their respective control groups. Cucurbitacin D also inhibited phosphorylation of STAT3 at Ser727 and Tyr705 residues as well as its downstream target genes c-Myc, and MMP9. Cucurbitacin D enhanced the expression of tumor suppressor microRNAs (miR-145, miRNA-143, and miRNA34a) in cervical cancer cells
Name Type Language
CUCURBITACIN D
Common Name English
19-NORLANOSTA-5,23-DIENE-3,11,22-TRIONE, 2,16,20,25-TETRAHYDROXY-9-METHYL-, (2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.,23E)-
Systematic Name English
NSC-521776
Code English
NSC-308606
Code English
ELATERICINE A
Common Name English
CUCURBITACINE D
Common Name English
ELATERICIN A
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID401032034
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
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NSC
521776
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
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WIKIPEDIA
Cucurbitacin D
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
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CHEBI
3943
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
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FDA UNII
5I62H4ORC7
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
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PUBCHEM
5281318
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
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CAS
3877-86-9
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY
NSC
308606
Created by admin on Sat Dec 16 09:14:32 GMT 2023 , Edited by admin on Sat Dec 16 09:14:32 GMT 2023
PRIMARY