Cucurbitacin D (BioDeep_00000000567)

Secondary id: BioDeep_00000404649, BioDeep_00000861747, BioDeep_00001867523

human metabolite PANOMIX_OTCML-2023 Endogenous

代谢物信息卡片

17-[(E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione

化学式: C30H44O7 (516.3086874)
中文名称: 葫芦素 D, 葫芦素D, 葫芦素 D
谱图信息: 最多检出来源 Macaca mulatta(otcml) 0.2%

分子结构信息

SMILES: CC(C)(O)C=CC(=O)C(C)(O)C1C(O)CC2(C)C3CC=C4C(CC(O)C(=O)C4(C)C)C3(C)C(=O)CC12C
InChI: 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

描述信息

Cucurbitacin D is a cucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at positions 5 and 23. It is a cucurbitacin, a secondary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It derives from a hydride of a lanostane.
Cucurbitacin D is a natural product found in Elaeocarpus chinensis, Elaeocarpus hainanensis, and other organisms with data available.
Cucurbitacin D is found in calabash. Cucurbitacin D is isolated from plants of the Cucurbitacea
Cucurbitacin D is an active component in Trichosanthes kirilowii, disrupts interactions between Hsp90 and two co-chaperones, Cdc37 and p23. Cucurbitacin D prevents Hsp90 client (Her2, Raf, Cdk6, pAkt) maturation without induction of the heat shock response. Anti-cancer activity[1].
Cucurbitacin D is an active component in Trichosanthes kirilowii, disrupts interactions between Hsp90 and two co-chaperones, Cdc37 and p23. Cucurbitacin D prevents Hsp90 client (Her2, Raf, Cdk6, pAkt) maturation without induction of the heat shock response. Anti-cancer activity[1].

同义名列表

22 个代谢物同义名

17-[(E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione; 14-[(4E)-2,6-dihydroxy-6-methyl-3-oxohept-4-en-2-yl]-4,13-dihydroxy-1,6,6,11,15-pentamethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-ene-5,17-dione; (2S,4R,23E)-2,16,20,25-tetrahydroxy-9beta,10,14-trimethyl-4,9-cyclo-9,10-seco-16alpha-cholesta-5,23-diene-1,11,22-trione; 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)-; 19-Norlanosta-5,23-diene-3,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2beta,9beta,10alpha,16alpha,23E)-; 19-Norlanosta-5,11,22-trione, 2,16,20,25-tetrahydroxy-9-methyl-, (2.beta.,9.beta.,10.alpha.,16.alpha.,23E)-; 19-Nor-9-beta,10-alpha-lanosta-5,23-diene-3,11,22-trione, 9-methyl-2-beta,16-alpha,20,25-tetrahydroxy-; (23E)-2beta,16alpha,20,25- tetrahydroxy-9beta-methyl-19-nor-10alpha-lanosta-5,23-diene-3,11,22-trione; 19-Norlanosta-5,23-diene-3,11,22-trione,2,16,20,25-tetrahydroxy-9-methyl-, (2b,9b,10a,16a,23E)-; 19-nor-9.beta.,23-diene-3,11,22-trione, 9-methyl-2.beta.,16.alpha.,20,25-tetrahydroxy-; (23E)-2beta,16alpha,20,25-tetrahydroxy-10alpha-cucurbita-5,23-diene-3,11,22-trione; Cucurbitacin D (Elatericin A); 23,24-dihydro-cucurbitacin D; Cucurbitacine (D); UNII-5I62H4ORC7; CUCURBITACINE D; Cucurbitacin D; Elatericine A; Neuro_000157; elatericin A; ST 30:5;O7; 5I62H4ORC7

数据库引用编号

22 个数据库交叉引用编号

ChEBI: CHEBI:3943
KEGG: C08796
PubChem: 5281318
PubChem: 5353546
PubChem: 2886
HMDB: HMDB0034695
Metlin: METLIN41669
ChEMBL: CHEMBL493646
Wikipedia: Cucurbitacin_D
Wikipedia: Cucurbitacin D
LipidMAPS: LMST01010106
MeSH: cucurbitacin D
ChemIDplus: 0003877869
KNApSAcK: C00003685
foodb: FDB013225
chemspider: 4510125
CAS: 3877-86-9
medchemexpress: HY-N1986
PMhub: MS000020201
PubChem: 10989
3DMET: B02417
NIKKAJI: J8.271F

分类词条

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

77 个相关的物种来源信息

115911 Achatinella: 10.1016/J.PHYTOCHEM.2006.03.005
3652 Bryonia dioica: 10.1016/S0031-9422(00)88975-X
3661 Cucurbita maxima: 10.1016/S0304-3835(02)00497-4
3677 Trichosanthes kirilowii: 10.1016/J.INTIMP.2009.01.006
181998 Leucopaxillus gentianeus: 10.1021/NP060213N
9606 Homo sapiens: 10.1007/S11306-021-01798-Z
190244 Helicteres angustifolia: 10.1016/J.PHYTOCHEM.2006.03.005
1526293 Elaeocarpus mastersii: 10.1016/S0031-9422(02)00232-7
34297 Datisca glomerata: 10.1039/P19830001333
133202 Physocarpus opulifolius: 10.1016/S0031-9422(98)00653-0
3677 Trichosanthes kirilowii:
200009 Begonia heracleifolia: 10.1055/S-2006-957460
1144447 Trichosanthes multiloba: 10.1248/YAKUSHI1947.109.9_677
1144443 Trichosanthes miyagii: 10.1248/YAKUSHI1947.109.9_677
654837 Trichosanthes tricuspidata: 10.1248/YAKUSHI1947.109.4_265
627488 Gurania subumbellata: 10.1021/NP50072A037
703182 Wilbrandia ebracteata: 10.1055/S-2006-959668
181998 Leucopaxillus gentianeus: 10.1021/NP060213N
388295 Luffa operculata:
184136 Cucurbita foetidissima: 10.1016/0031-9422(88)84112-8
2306772 Gonystylus keithii: 10.1021/NP50112A015
463186 Bryonia verrucosa: 10.1080/10575639908048799
61884 Bryonia cretica:
3652 Bryonia dioica: 10.1016/0040-4020(76)85214-3
386153 Cogniauxia podolaena: 10.1055/S-2008-1081341
869827 Cucumis sativus var. sativus: 10.1021/JF00103A051
226049 Iberis umbellata:
3679 Ecballium elaterium:
1421037 Begonia parviflora: 10.1351/PAC199971061089
387122 Acanthosicyos horridus: 10.1016/S0031-9422(00)81235-2
3661 Cucurbita maxima: 10.1007/BF00987375
3663 Cucurbita pepo:
2569957 Conobea scoparioides: 10.1021/NP50113A004
1082500 Elaeocarpus hainanensis: 10.1055/S-2008-1081356
388300 Neoalsomitra clavigera: 10.1016/0031-9422(94)00608-V
447128 Neoalsomitra integrifoliola: 10.1016/0031-9422(94)00608-V
1008905 Elaeocarpus chinensis: 10.1055/S-0032-1320924
115911 Achatinella: 10.1016/J.PHYTOCHEM.2006.03.005
3652 Bryonia dioica: 10.1016/S0031-9422(00)88975-X
3661 Cucurbita maxima: 10.1016/S0304-3835(02)00497-4
3677 Trichosanthes kirilowii: 10.1016/J.INTIMP.2009.01.006
181998 Leucopaxillus gentianeus: 10.1021/NP060213N
9606 Homo sapiens: 10.1007/S11306-021-01798-Z
190244 Helicteres angustifolia: 10.1016/J.PHYTOCHEM.2006.03.005
1526293 Elaeocarpus mastersii: 10.1016/S0031-9422(02)00232-7
34297 Datisca glomerata: 10.1039/P19830001333
133202 Physocarpus opulifolius: 10.1016/S0031-9422(98)00653-0
3677 Trichosanthes kirilowii:
200009 Begonia heracleifolia: 10.1055/S-2006-957460
1144447 Trichosanthes multiloba: 10.1248/YAKUSHI1947.109.9_677
1144443 Trichosanthes miyagii: 10.1248/YAKUSHI1947.109.9_677
654837 Trichosanthes tricuspidata: 10.1248/YAKUSHI1947.109.4_265
627488 Gurania subumbellata: 10.1021/NP50072A037
703182 Wilbrandia ebracteata: 10.1055/S-2006-959668
181998 Leucopaxillus gentianeus: 10.1021/NP060213N
388295 Luffa operculata:
184136 Cucurbita foetidissima: 10.1016/0031-9422(88)84112-8
2306772 Gonystylus keithii: 10.1021/NP50112A015
463186 Bryonia verrucosa: 10.1080/10575639908048799
61884 Bryonia cretica:
3652 Bryonia dioica: 10.1016/0040-4020(76)85214-3
386153 Cogniauxia podolaena: 10.1055/S-2008-1081341
869827 Cucumis sativus var. sativus: 10.1021/JF00103A051
226049 Iberis umbellata:
3679 Ecballium elaterium:
1421037 Begonia parviflora: 10.1351/PAC199971061089
387122 Acanthosicyos horridus: 10.1016/S0031-9422(00)81235-2
3661 Cucurbita maxima: 10.1007/BF00987375
3663 Cucurbita pepo:
2569957 Conobea scoparioides: 10.1021/NP50113A004
1082500 Elaeocarpus hainanensis: 10.1055/S-2008-1081356
388300 Neoalsomitra clavigera: 10.1016/0031-9422(94)00608-V
447128 Neoalsomitra integrifoliola: 10.1016/0031-9422(94)00608-V
1008905 Elaeocarpus chinensis: 10.1055/S-0032-1320924
9606 Homo sapiens: -
210372 Aquilaria sinensis: -
33090 Plants: -

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Xinke Zhang, Guoshuai Zhang, Qi Yan, Bashir Ahmad, Jin Pei, Linfang Huang. Quality variation and salt-alkali-tolerance mechanism of Cynomorium songaricum: Interacting from microbiome-transcriptome-metabolome. The Science of the total environment. 2024 Apr; 919(?):170801. doi: 10.1016/j.scitotenv.2024.170801. [PMID: 38340858]
Muhammed Mehdi Üremiş, Yusuf Türköz, Nuray Üremiş. Investigation of apoptotic effects of Cucurbitacin D, I, and E mediated by Bax/Bcl-xL, caspase-3/9, and oxidative stress modulators in HepG2 cell line. Drug development research. 2024 Apr; 85(2):e22174. doi: 10.1002/ddr.22174. [PMID: 38494997]
Muhammed Mehdi Üremiş, Nuray Üremiş, Emir Tosun, Merve Durhan, Yılmaz Çiğremiş, Ahmet Baysar, Yusuf Türköz. Cucurbitacin D Inhibits the Proliferation of HepG2 Cells and Induces Apoptosis by Modulating JAK/STAT3, PI3K/Akt/mTOR and MAPK Signaling Pathways. Current cancer drug targets. 2022; 22(11):931-944. doi: 10.2174/1568009622666220623141158. [PMID: 35786188]
Duo Wang, Mengyue Shen, Noriaki Kitamura, Yusuke Sennari, Kentaro Morita, Junichi Tsukada, Tamotsu Kanazawa, Yasuhiro Yoshida. Mitogen-activated protein kinases are involved in cucurbitacin D-induced antitumor effects on adult T-cell leukemia cells. Investigational new drugs. 2021 02; 39(1):122-130. doi: 10.1007/s10637-020-00997-0. [PMID: 32914311]
Jin Mo Ku, Se Hyang Hong, Hyo In Kim, Min Jeong Kim, Su-Kyoung Kim, Minkyu Kim, Seok Young Choi, Jeongkoo Park, Hyun Koo Kim, Ji Hye Kim, Hye Sook Seo, Yong Cheol Shin, Seong-Gyu Ko. Synergistic anticancer effect of combined use of Trichosanthes kirilowii with cisplatin and pemetrexed enhances apoptosis of H1299 non-small-cell lung cancer cells via modulation of ErbB3. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Jan; 66(?):153109. doi: 10.1016/j.phymed.2019.153109. [PMID: 31790894]
Catherine Jacquot, Benedicte Rousseau, Delphine Carbonnelle, Ioanna Chinou, Marine Malleter, Christophe Tomasoni, Christos Roussakis. Cucurbitacin-D-induced CDK1 mRNA up-regulation causes proliferation arrest of a non-small cell lung carcinoma cell line (NSCLC-N6). Anticancer research. 2014 Sep; 34(9):4797-806. doi: . [PMID: 25202060]
Samuel A Spear, Sarah S Burns, Janet L Oblinger, Yulin Ren, Li Pan, A Douglas Kinghorn, D Bradley Welling, Long-Sheng Chang. Natural compounds as potential treatments of NF2-deficient schwannoma and meningioma: cucurbitacin D and goyazensolide. Otology & neurotology : official publication of the American Otological Society, American Neurotology Society [and] European Academy of Otology and Neurotology. 2013 Oct; 34(8):1519-27. doi: 10.1097/mao.0b013e3182956169. [PMID: 23928514]
Li Pan, Yeonjoong Yong, Ye Deng, Daniel D Lantvit, Tran Ngoc Ninh, Heebyung Chai, Esperanza J Carcache de Blanco, Djaja D Soejarto, Steven M Swanson, A Douglas Kinghorn. Isolation, structure elucidation, and biological evaluation of 16,23-epoxycucurbitacin constituents from Eleaocarpus chinensis. Journal of natural products. 2012 Mar; 75(3):444-52. doi: 10.1021/np200879p. [PMID: 22239601]
Yingrou Wei, Guocai Wang, Xiaoqi Zhang, Ying Wang, Wencai Ye. [Studies on chemical constituents in roots of Helicteres angustifolia]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2011 May; 36(9):1193-7. doi: . [PMID: 21842648]
Shamim Sahranavard, Farzaneh Naghibi, Karsten Siems, Kristina Jenett-Siems. New cucurbitane-type triterpenoids from Bryonia aspera. Planta medica. 2010 Jul; 76(10):1014-7. doi: 10.1055/s-0029-1240840. [PMID: 20108178]
Rony Abou-Khalil, Alia Jraij, Jacques Magdalou, Naïm Ouaini, Daniel Tome, Hélène Greige-Gerges. Interaction of cucurbitacins with human serum albumin: Thermodynamic characteristics and influence on the binding of site specific ligands. Journal of photochemistry and photobiology. B, Biology. 2009 Jun; 95(3):189-95. doi: 10.1016/j.jphotobiol.2009.03.005. [PMID: 19380237]
Norito Takahashi, Yasuhiro Yoshida, Tsutomu Sugiura, Koji Matsuno, Akihiro Fujino, Uki Yamashita. Cucurbitacin D isolated from Trichosanthes kirilowii induces apoptosis in human hepatocellular carcinoma cells in vitro. International immunopharmacology. 2009 Apr; 9(4):508-13. doi: 10.1016/j.intimp.2009.01.006. [PMID: 19185617]
Jean Théophile Banzouzi, Patrice Njomnang Soh, Bernard Mbatchi, Adrien Cavé, Suzanne Ramos, Pascal Retailleau, Olga Rakotonandrasana, Antoine Berry, Françoise Benoit-Vical. Cogniauxia podolaena: bioassay-guided fractionation of defoliated stems, isolation of active compounds, antiplasmodial activity and cytotoxicity. Planta medica. 2008 Oct; 74(12):1453-6. doi: 10.1055/s-2008-1081341. [PMID: 18704883]
H Greige-Gerges, R Abou Khalil, R Chahine, C Haddad, W Harb, N Ouaini. Effect of cucurbitacins on bilirubin-albumin binding in human plasma. Life sciences. 2007 Jan; 80(6):579-85. doi: 10.1016/j.lfs.2006.10.005. [PMID: 17097690]
Hamta Madari, Robert S Jacobs. An analysis of cytotoxic botanical formulations used in the traditional medicine of ancient Persia as abortifacients. Journal of natural products. 2004 Aug; 67(8):1204-10. doi: 10.1021/np049953r. [PMID: 15332833]
Nelson Rodriguez, Yelkaira Vasquez, Ahmed A Hussein, Phyllis D Coley, Pablo N Solis, Mahabir P Gupta. Cytotoxic cucurbitacin constituents from Sloanea zuliaensis. Journal of natural products. 2003 Nov; 66(11):1515-6. doi: 10.1021/np0303106. [PMID: 14640532]
Hyuncheol Oh, Yeun-Ja Mun, Sook-Jung Im, Seung Yon Lee, Ho Joon Song, Ho-Sub Lee, Won-Hong Woo. Cucurbitacins from Trichosanthes kirilowii as the inhibitory components on tyrosinase activity and melanin synthesis of B16/F10 melanoma cells. Planta medica. 2002 Sep; 68(9):832-3. doi: 10.1055/s-2002-34418. [PMID: 12357397]
Aiko Ito, Hee-Byung Chai, Dongho Lee, Leonardus B S Kardono, Soedarsono Riswan, Norman R Farnsworth, Geoffrey A Cordell, John M Pezzuto, A Douglas Kinghorn. Ellagic acid derivatives and cytotoxic cucurbitacins from Elaeocarpus mastersii. Phytochemistry. 2002 Sep; 61(2):171-4. doi: 10.1016/s0031-9422(02)00232-7. [PMID: 12169311]
L Dinan, P Whiting, J P Girault, R Lafont, T S Dhadialla, D E Cress, B Mugat, C Antoniewski, J A Lepesant. Cucurbitacins are insect steroid hormone antagonists acting at the ecdysteroid receptor. The Biochemical journal. 1997 Nov; 327 ( Pt 3)(?):643-50. doi: 10.1042/bj3270643. [PMID: 9581538]
M E Barbercheck, J Wang. Effect of cucurbitacin D on in vitro growth of Xenorhabdus and Photorhabdus spp., symbiotic bacteria of entomopathogenic nematodes. Journal of invertebrate pathology. 1996 Sep; 68(2):141-5. doi: 10.1006/jipa.1996.0071. [PMID: 8858910]
L L Musza, P Speight, S McElhiney, C J Barrow, A M Gillum, R Cooper, L M Killar. Cucurbitacins, cell adhesion inhibitors from Conobea scoparioides. Journal of natural products. 1994 Nov; 57(11):1498-502. doi: 10.1021/np50113a004. [PMID: 7852999]