Dolastatin 10 (BioDeep_00000395706)

Marine Natural Products Antitumor activity

代谢物信息卡片

化学式: C42H68N6O6S (784.4920788)
中文名称: 尾海兔素10, 杜拉司汀10
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.11%

Reviewed

Last reviewed on 2024-10-09.

Cite this Page

Dolastatin 10. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/dolastatin_10 (retrieved 2024-11-26) (BioDeep RN: BioDeep_00000395706). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CCC(C)C(C(CC(=O)N1CCCC1C(C(C)C(=O)NC(CC2=CC=CC=C2)C3=NC=CS3)OC)OC)N(C)C(=O)C(C(C)C)NC(=O)C(C(C)C)N(C)C
InChI: InChI=1S/C42H68N6O6S/c1-13-28(6)37(47(10)42(52)35(26(2)3)45-40(51)36(27(4)5)46(8)9)33(53-11)25-34(49)48-22-17-20-32(48)38(54-12)29(7)39(50)44-31(41-43-21-23-55-41)24-30-18-15-14-16-19-30/h14-16,18-19,21,23,26-29,31-33,35-38H,13,17,20,22,24-25H2,1-12H3,(H,44,50)(H,45,51)/t28-,29+,31-,32-,33+,35-,36-,37-,38+/m0/s1

描述信息

Dolastatin 10 is a tetrapeptide that is isolated from the sea hare Dolabella auricularia. It is a potent anticancer agent which inhibits tubulin polymerization. It has a role as an animal metabolite, a marine metabolite, an antineoplastic agent, an apoptosis inducer and a microtubule-destabilising agent. It is a member of 1,3-thiazoles and a tetrapeptide. It is functionally related to a L-valine.
Dolastatin 10 has been used in trials studying the treatment of Sarcoma, Leukemia, Lymphoma, Liver Cancer, and Kidney Cancer, among others.
Dolastatin 10 is a natural product found in Symploca, Caldora penicillata, and other organisms with data available.
Dolastatin 10 is a pentapeptide originally isolated from the marine mollusk Dolabella auricularia with potential antineoplastic activity. Binding to tubulin, Dolastatin 10 inhibits microtubule assembly, resulting in the formation of tubulin aggregates and inhibition of mitosis. This agent also induces tumor cell apoptosis through a mechanism involving bcl-2, an oncoprotein that is overexpressed in some cancers. (NCI04)
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators
D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
Dolastatin 10 (DLS 10) is a potent antimitotic peptide that inhibits tubulin polymerization.

同义名列表

18 个代谢物同义名

(2S)-2-[[(2S)-2-(dimethylamino)-3-methylbutanoyl]amino]-N-[(3R,4S,5S)-3-methoxy-1-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino]propyl]pyrrolidin-1-yl]-5-methyl-1-oxoheptan-4-yl]-N,3-dimethylbutanamide; (S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N-((3R,4S,5S)-3-methoxy-1-((S)-2-((1R,2R)-1-methoxy-2-methyl-3-oxo-3-(((S)-2-phenyl-1-(thiazol-2-yl)ethyl)amino)propyl)pyrrolidin-1-yl)-5-methyl-1-oxoheptan-4-yl)-N,3-dimethylbutanamide; L-Valinamide, N,N-dimethyl-L-valyl-N-(2-methoxy-4-(2-(1-methoxy-2-methyl-3-oxo-3-((2-phenyl-1-(2-thiazolyl)ethyl)amino)propyl)-1-pyrrolidinyl)-1-(1-methylpropyl)-4-oxobutyl)-N-methyl-, (2S-(1(1R*(R*),2S*),2R*(1S*,2S*,3(R*))))-; N,N-DIMETHYL-VAL-N-(2-METHOXY-4-(2-(1-METHOXY-2-METHYL-3-OXO-3-((2-PHENYL-1-(2-THIAZOLYL)ETHYL)AMINO)PROPYL)-1-PYRROLIDINYL)-1-(1-METHYLPROPYL)-4-OXOBUTYL)-N-METHYL-VALINAMIDE (2S-(1(1R*(R*),2S*),2R*(1S*,2S*,3(R*)))); L-Valinamide, N,N-dimethyl-L-valyl-N-[(1S,2R)-2-methoxy-4-[(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-[[(1S)-2-phenyl-1-(2-thiazolyl)ethyl]amino]propyl]-1-pyrrolidinyl]-1-[(1S)-1-methylpropyl]-4-oxobutyl]-N-methyl-; L-VALINAMIDE, N,N-DIMETHYL-L-VALYL-N-((1S,2R)-2-METHOXY-4-((2S)-2-((1R,2R)-1-METHOXY-2-METHYL-3-OXO-3-(((1S)-2-PHENYL-1-(2-THIAZOLYL)ETHYL)AMINO)PROPYL)-1-PYRROLIDINYL)-1-((1S)-1-METHYLPROPYL)-4-OXOBUTYL)-N-METHYL-; N,N-dimethyl-L-valyl-N-[(3R,4S,5S)-3-methoxy-1-{(2S)-2-[(1R,2R)-1-methoxy-2-methyl-3-oxo-3-{[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]amino}propyl]pyrrolidin-1-yl}-5-methyl-1-oxoheptan-4-yl]-N-methyl-L-valinamide; deo-dolastatin 10; isodolastatin 10; Dolostatin 10; Dolastatin-10; Dolastatin 10; Deo-Dola 10; Dolastin; DLS 10; SR6; NSC 376128; Dolastatin 10

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:67357
KEGG: C11280
PubChem: 9810929
DrugBank: DB12730
ChEMBL: CHEMBL39541
MeSH: dolastatin 10
ChemIDplus: 0110417884
KNApSAcK: C00045865
KNApSAcK: C00044726
CAS: 110417-88-4
medchemexpress: HY-15580
MetaboLights: MTBLC67357
NIKKAJI: J359.711C
PubChem: 13457
KNApSAcK: 67357

分类词条

大环内酯类抗生素

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)

0 个相关的物种来源信息

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

Gang Gao, Yanbing Wang, Huiming Hua, Dahong Li, Chunlan Tang. Marine Antitumor Peptide Dolastatin 10: Biological Activity, Structural Modification and Synthetic Chemistry. Marine drugs. 2021 Jun; 19(7):. doi: 10.3390/md19070363. [PMID: 34202685]
George R Pettit, Noeleen Melody, Jean-Charles Chapuis. Antineoplastic Agents. 606. The Betulastatins. Journal of natural products. 2018 03; 81(3):458-464. doi: 10.1021/acs.jnatprod.7b00536. [PMID: 29303263]
Kirandeep Kaur, Meenakshi Jain, Tarandeep Kaur, Rahul Jain. Antimalarials from nature. Bioorganic & medicinal chemistry. 2009 May; 17(9):3229-56. doi: 10.1016/j.bmc.2009.02.050. [PMID: 19299148]
T Woyke, G R Pettit, G Winkelmann, R K Pettit. In vitro activities and postantifungal effects of the potent dolastatin 10 derivative auristatin PHE. Antimicrobial agents and chemotherapy. 2001 Dec; 45(12):3580-4. doi: 10.1128/aac.45.12.3580-3584.2001. [PMID: 11709343]
K Margolin, J Longmate, T W Synold, D R Gandara, J Weber, R Gonzalez, M J Johansen, R Newman, T Baratta, J H Doroshow. Dolastatin-10 in metastatic melanoma: a phase II and pharmokinetic trial of the California Cancer Consortium. Investigational new drugs. 2001; 19(4):335-40. doi: 10.1023/a:1010626230081. [PMID: 11561695]
T Madden, H T Tran, D Beck, R Huie, R A Newman, L Pusztai, J J Wright, J L Abbruzzese. Novel marine-derived anticancer agents: a phase I clinical, pharmacological, and pharmacodynamic study of dolastatin 10 (NSC 376128) in patients with advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research. 2000 Apr; 6(4):1293-301. doi: NULL. [PMID: 10778954]
W R Huie, S S Wong. Improvement in assay sensitivity for plasma dolastatin-10 using capillary electrophoresis at elevated temperatures. Journal of chromatography. B, Biomedical sciences and applications. 1999 Jun; 729(1-2):1-10. doi: 10.1016/s0378-4347(99)00038-9. [PMID: 10410922]
H C Pitot, E A McElroy, J M Reid, A J Windebank, J A Sloan, C Erlichman, P G Bagniewski, D L Walker, J Rubin, R M Goldberg, A A Adjei, M M Ames. Phase I trial of dolastatin-10 (NSC 376128) in patients with advanced solid tumors. Clinical cancer research : an official journal of the American Association for Cancer Research. 1999 Mar; 5(3):525-31. doi: NULL. [PMID: 10100703]
J C Mirsalis, J Schindler-Horvat, J R Hill, J E Tomaszewski, S J Donohue, C A Tyson. Toxicity of dolastatin 10 in mice, rats and dogs and its clinical relevance. Cancer chemotherapy and pharmacology. 1999; 44(5):395-402. doi: 10.1007/s002800050995. [PMID: 10501913]
R K Pettit, G R Pettit, K C Hazen. Specific activities of dolastatin 10 and peptide derivatives against Cryptococcus neoformans. Antimicrobial agents and chemotherapy. 1998 Nov; 42(11):2961-5. doi: 10.1128/aac.42.11.2961. [PMID: 9797233]
D A Garteiz, T Madden, D E Beck, W R Huie, K T McManus, J L Abbruzzese, W Chen, R A Newman. Quantitation of dolastatin-10 using HPLC/electrospray ionization mass spectrometry: application in a phase I clinical trial. Cancer chemotherapy and pharmacology. 1998; 41(4):299-306. doi: 10.1007/s002800050743. [PMID: 9488599]
W R Huie, R A Newman, T Hutto, T Madden. High-performance capillary electrophoresis measurement of dolastatin-10. Journal of chromatography. B, Biomedical sciences and applications. 1997 Jun; 693(2):451-61. doi: 10.1016/s0378-4347(97)00018-2. [PMID: 9210452]
M J Borgnia, G D Eytan, Y G Assaraf. Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. The Journal of biological chemistry. 1996 Feb; 271(6):3163-71. doi: 10.1074/jbc.271.6.3163. [PMID: 8621716]
G W Aherne, A Hardcastle, M Valenti, A Bryant, P Rogers, G R Pettit, J K Srirangam, L R Kelland. Antitumour evaluation of dolastatins 10 and 15 and their measurement in plasma by radioimmunoassay. Cancer chemotherapy and pharmacology. 1996; 38(3):225-32. doi: 10.1007/s002800050475. [PMID: 8646796]
R A Newman, A Fuentes, J M Covey, J A Benvenuto. Preclinical pharmacology of the natural marine product dolastatin 10 (NSC 376128). Drug metabolism and disposition: the biological fate of chemicals. 1994 May; 22(3):428-32. doi: NULL. [PMID: 8070319]
R Bai, Z A Cichacz, C L Herald, G R Pettit, E Hamel. Spongistatin 1, a highly cytotoxic, sponge-derived, marine natural product that inhibits mitosis, microtubule assembly, and the binding of vinblastine to tubulin. Molecular pharmacology. 1993 Oct; 44(4):757-66. doi: . [PMID: 8232226]