CUCURBITACIN D

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 Search

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

Molecular Formula	C30H44O7
Molecular Weight	516.6662
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	8 / 9
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=26009687
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

Condition	Modality	Targets	Highest Phase	Product
Cervical cancer 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27824155	Primary		Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26169986	Primary		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The cucurbitacins E, D and I: investigation of their cytotoxicity toward human chondrosarcoma SW 1353 cell line and their biotransformation in man liver.	2013 Feb 4	23194827

Patents

Sample Use Guides

In Vivo Use Guide

athymic nude mice: 1 mg/kg body weight injected intra-tumorally 3 days a week

Route of Administration: Other

In Vitro Use Guide

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

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:14:32 GMT 2023` Edited by `admin` on `Sat Dec 16 09:14:32 GMT 2023`
Record UNII	5I62H4ORC7
Record Status	`Validated (UNII)`
Record Version

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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