Di-2-propenyl sulfide (BioDeep_00000003857)
Secondary id: BioDeep_00000866610, BioDeep_00001867734
human metabolite
代谢物信息卡片
3-(prop-2-en-1-ylsulfanyl)prop-1-ene
化学式: C6H10S (114.050318)
中文名称: 二烯丙基硫醚
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: C=CCSCC=C
InChI: InChI=1S/C6H10S/c1-3-5-7-6-4-2/h3-4H,1-2,5-6H2
描述信息
Di-2-propenyl sulfide, also known as allyl sulfide or 3-allylsulfanyl-propene, is a member of the class of compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS. Di-2-propenyl sulfide is a garlic, horseradish, and metallic tasting compound and can be found in a number of food items such as onion-family vegetables, garden cress, horseradish, and brassicas, which makes di-2-propenyl sulfide a potential biomarker for the consumption of these food products. Di-2-propenyl sulfide can be found primarily in urine.
Di-2-propenyl sulfide, also known as allyl sulfide or garlic oil, belongs to the class of organic compounds known as allyl sulfur compounds. Allyl sulfur compounds are compounds containing an allylsulfur group, with the general structure H2C(=CH2)CS. Di-2-propenyl sulfide is possibly neutral. Di-2-propenyl sulfide is a garlic, horseradish, and metallic tasting compound. di-2-propenyl sulfide has been detected, but not quantified, in several different foods, such as wild leeks, herbs and spices, brassicas, radish, and garden onions.
D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors
D020011 - Protective Agents > D016588 - Anticarcinogenic Agents
D020011 - Protective Agents > D000975 - Antioxidants
D000970 - Antineoplastic Agents
同义名列表
21 个代谢物同义名
3-(prop-2-en-1-ylsulfanyl)prop-1-ene; 3-(Allylsulfanyl)-1-propene; 3,3-Thiobis-1-propene, 9ci; Di-2-propenyl sulphide; Di-2-propenyl-sulphane; 4-Thia-1,6-heptadiene; Di-2-propenyl sulfide; Di-2-propenyl-sulfane; Diallyl monosulfide; Dially monosulfide; Diallyl thioether; Allyl monosulfide; Diallyl sulphide; Thioallyl ether; DIALLYL SULFIDE; Allyl sulphide; Diallylsulfide; Allyl Sulfide; Garlic oil; oil garlic; FEMA 2042
数据库引用编号
14 个数据库交叉引用编号
- ChEBI: CHEBI:4489
- KEGG: C08370
- PubChem: 11617
- HMDB: HMDB0036491
- Metlin: METLIN44102
- ChEMBL: CHEMBL170458
- KNApSAcK: C00001244
- foodb: FDB003585
- chemspider: 11128
- CAS: 592-88-1
- PMhub: MS000012771
- PubChem: 10566
- NIKKAJI: J6.765B
- RefMet: Di-2-propenyl sulfide
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
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)
7 个相关的物种来源信息
- 105301 - Allium angulosum: 10.1099/0022-1317-50-7-646
- 130426 - Allium chinense: 10.1186/1756-3305-7-184
- 74896 - Allium neapolitanum: 10.1099/0022-1317-50-7-646
- 105309 - Allium ramosum: 10.1099/0022-1317-50-7-646
- 4682 - Allium sativum:
- 9606 - Homo sapiens: -
- 353996 - Mansoa alliacea: 10.1021/JF00125A014
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
- Sakhawat Shah, Karam Khamis Elgizawy, Meng-Ya Wu, Hucheng Yao, Wen-Han Yan, Yu Li, Xiao-Ping Wang, Gang Wu, Feng-Lian Yang. Diallyl Trisulfide Causes Male Infertility with Oligoasthenoteratospermia in Sitotroga cerealella through the Ubiquitin-Proteasome Pathway.
Cells.
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International journal of biological macromolecules.
2023 Jul; 243(?):125160. doi:
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International journal of molecular sciences.
2023 Jun; 24(11):. doi:
10.3390/ijms24119627. [PMID: 37298578] - Jeanne M Davidsen, Samuel M Cohen, Gerhard Eisenbrand, Shoji Fukushima, Nigel J Gooderham, F Peter Guengerich, Stephen S Hecht, Ivonne M C M Rietjens, Thomas J Rosol, Christie L Harman, Danarubini Ramanan, Sean V Taylor. FEMA GRAS assessment of natural flavor complexes: Asafetida oil, garlic oil and onion oil.
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2023 02; 12(4):. doi:
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PloS one.
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Ecotoxicology and environmental safety.
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Meat science.
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PloS one.
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Molecules (Basel, Switzerland).
2019 Dec; 24(24):. doi:
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Bioorganic & medicinal chemistry.
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Life sciences.
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TheScientificWorldJournal.
2015; 2015(?):958192. doi:
10.1155/2015/958192. [PMID: 25705718] - Imam Hassouna, Hany Ibrahim, Faten Abdel Gaffar, Ibrahim El-Elaimy, Heba Abdel Latif. Simultaneous administration of hesperidin or garlic oil modulates diazinon-induced hemato- and immunotoxicity in rats.
Immunopharmacology and immunotoxicology.
2015; 37(5):442-9. doi:
10.3109/08923973.2015.1081932. [PMID: 26466643] - S Ansar, M Iqbal, N AlJameil. Diallyl sulphide, a component of garlic, abrogates ferric nitrilotriacetate-induced oxidative stress and renal damage in rats.
Human & experimental toxicology.
2014 Dec; 33(12):1209-16. doi:
10.1177/0960327114524237. [PMID: 24596035] - Michael L McCaskill, Eleanor Rogan, Ronald D Thomas. Diallyl sulfide inhibits diethylstilbestrol induced DNA damage in human breast epithelial cells (MCF-10A).
Steroids.
2014 Dec; 92(?):96-100. doi:
10.1016/j.steroids.2014.09.005. [PMID: 25278253] - Miyoung Yoo, Sunyoung Kim, Sanghee Lee, Dongbin Shin. Validated HPLC method and temperature stabilities for oil-soluble organosulfur compounds in garlic macerated oil.
Journal of chromatographic science.
2014 Nov; 52(10):1165-72. doi:
10.1093/chromsci/bmt166. [PMID: 24243685] - Su-Chen Ho, Min-Sheng Su. Evaluating the anti-neuroinflammatory capacity of raw and steamed garlic as well as five organosulfur compounds.
Molecules (Basel, Switzerland).
2014 Oct; 19(11):17697-714. doi:
10.3390/molecules191117697. [PMID: 25365295] - Wen-Ru Li, Qing-Shan Shi, Qing Liang, Xiao-Mo Huang, Yi-Ben Chen. Antifungal effect and mechanism of garlic oil on Penicillium funiculosum.
Applied microbiology and biotechnology.
2014 Oct; 98(19):8337-46. doi:
10.1007/s00253-014-5919-9. [PMID: 25012787] - Ziqian Xu, Hairi Wang, Yafei Chen, Geqi Mao, Yue Hu, Tao Zeng, Keqin Xie. [Preventive effects of garlic oil against the benzene-induced hematotoxicity in mice].
Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases.
2014 May; 32(5):373-5. doi:
". [PMID: 25169096] - Amina Hamed Ahmad Alobaidi. Effect of Nigella sativa and Allium sativum coadminstered with simvastatin in dyslipidemia patients: a prospective, randomized, double-blind trial.
Anti-inflammatory & anti-allergy agents in medicinal chemistry.
2014 Mar; 13(1):68-74. doi:
10.2174/18715230113129990013. [PMID: 23848231] - F Kirkpinar, H B Ünlü, M Serdaroğlu, G Y Turp. Effects of dietary oregano and garlic essential oils on carcass characteristics, meat composition, colour, pH and sensory quality of broiler meat.
British poultry science.
2014; 55(2):157-66. doi:
10.1080/00071668.2013.879980. [PMID: 24404997] - D S Prokof'eva, N V Goncharov. [Effects of biogenic and abiogenic disulphides upon endothelial cells in culture: comparison of three methods of viability assessment].
Tsitologiia.
2014; 56(6):410-8. doi:
. [PMID: 25696977] - Hanem Saad Abdultawab, Nasra N Ayuob. Can garlic oil ameliorate diabetes-induced oxidative stress in a rat liver model? A correlated histological and biochemical study.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2013 Sep; 59(?):650-6. doi:
10.1016/j.fct.2013.07.009. [PMID: 23856496] - Tao Zeng, Yang Li, Cui-Li Zhang, Li-Hua Yu, Zhen-Ping Zhu, Xiu-Lan Zhao, Ke-Qin Xie. Garlic oil suppressed the hematological disorders induced by chemotherapy and radiotherapy in tumor-bearing mice.
Journal of food science.
2013 Jun; 78(6):H936-42. doi:
10.1111/1750-3841.12137. [PMID: 23772706] - J Robyn, G Rasschaert, D Hermans, F Pasmans, M Heyndrickx. Is allicin able to reduce Campylobacter jejuni colonization in broilers when added to drinking water?.
Poultry science.
2013 May; 92(5):1408-18. doi:
10.3382/ps.2012-02863. [PMID: 23571353] - S M Aboelhadid, A A Kamel, W M Arafa, K A Shokier. Effect of Allium sativum and Allium cepa oils on different stages of Boophilus annulatus.
Parasitology research.
2013 May; 112(5):1883-90. doi:
10.1007/s00436-013-3344-0. [PMID: 23435922] - Sergio Casella, Michele Leonardi, Bernardo Melai, Filippo Fratini, Luisa Pistelli. The role of diallyl sulfides and dipropyl sulfides in the in vitro antimicrobial activity of the essential oil of garlic, Allium sativum L., and leek, Allium porrum L.
Phytotherapy research : PTR.
2013 Mar; 27(3):380-3. doi:
10.1002/ptr.4725. [PMID: 22610968] - Zhi Zhu, Suqin Hang, Honglong Zhu, Sheng Zhong, Shengyong Mao, Weiyun Zhu. Effects of garlic oil on milk fatty acid profile and lipogenesis-related gene expression in mammary gland of dairy goats.
Journal of the science of food and agriculture.
2013 Feb; 93(3):560-7. doi:
10.1002/jsfa.5829. [PMID: 22886566] - Chung-Ren Jan, Horng-Ren Lo, Chung-Yi Chen, Soong-Yu Kuo. Effect of allyl sulfides from garlic essential oil on intracellular ca2+ levels in renal tubular cells.
Journal of natural products.
2012 Dec; 75(12):2101-7. doi:
10.1021/np3005248. [PMID: 23163425] - Sevdan Yılmaz, Sebahattin Ergün. Effects of garlic and ginger oils on hematological and biochemical variables of sea bass Dicentrarchus labrax.
Journal of aquatic animal health.
2012 Dec; 24(4):219-24. doi:
10.1080/08997659.2012.711266. [PMID: 23043295] - Raquel Urtasun, Francisco Javier Cubero, Natalia Nieto. Oxidative stress modulates KLF6Full and its splice variants.
Alcoholism, clinical and experimental research.
2012 Nov; 36(11):1851-62. doi:
10.1111/j.1530-0277.2012.01798.x. [PMID: 22486562] - Andres A Caro, Luke W Adlong, Samuel J Crocker, Michael W Gardner, Emily F Luikart, Liz U Gron. Effect of garlic-derived organosulfur compounds on mitochondrial function and integrity in isolated mouse liver mitochondria.
Toxicology letters.
2012 Oct; 214(2):166-74. doi:
10.1016/j.toxlet.2012.08.017. [PMID: 22960305] - Hsiao-Chi Wang, Jung Pao, Shuw-Yuan Lin, Lee-Yan Sheen. Molecular mechanisms of garlic-derived allyl sulfides in the inhibition of skin cancer progression.
Annals of the New York Academy of Sciences.
2012 Oct; 1271(?):44-52. doi:
10.1111/j.1749-6632.2012.06743.x. [PMID: 23050963] - Heather Hajovsky, Gang Hu, Yakov Koen, Diganta Sarma, Wenqi Cui, David S Moore, Jeff L Staudinger, Robert P Hanzlik. Metabolism and toxicity of thioacetamide and thioacetamide S-oxide in rat hepatocytes.
Chemical research in toxicology.
2012 Sep; 25(9):1955-63. doi:
10.1021/tx3002719. [PMID: 22867114] - Patrick Krumm, Teresa Giraldez, Diego Alvarez de la Rosa, Wolfgang G Clauss, Martin Fronius, Mike Althaus. Thiol-reactive compounds from garlic inhibit the epithelial sodium channel (ENaC).
Bioorganic & medicinal chemistry.
2012 Jul; 20(13):3979-84. doi:
10.1016/j.bmc.2012.05.021. [PMID: 22668601] - Catherine P Haar, Preetha Hebbar, Gerald C Wallace, Arabinda Das, William A Vandergrift, Joshua A Smith, Pierre Giglio, Sunil J Patel, Swapan K Ray, Naren L Banik. Drug resistance in glioblastoma: a mini review.
Neurochemical research.
2012 Jun; 37(6):1192-200. doi:
10.1007/s11064-011-0701-1. [PMID: 22228201] - Kuang-Chi Lai, Chao-Lin Kuo, Heng-Chien Ho, Jai-Sing Yang, Chia-Yu Ma, Hsu-Feng Lu, Hui-Ying Huang, Fu-Shin Chueh, Chien-Chih Yu, Jing-Gung Chung. Diallyl sulfide, diallyl disulfide and diallyl trisulfide affect drug resistant gene expression in colo 205 human colon cancer cells in vitro and in vivo.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2012 May; 19(7):625-30. doi:
10.1016/j.phymed.2012.02.004. [PMID: 22397993] - Kabilan Velliyagounder, Krishnaraj Ganeshnarayan, Senthil Kumar Velusamy, Daniel H Fine. In vitro efficacy of diallyl sulfides against the periodontopathogen Aggregatibacter actinomycetemcomitans.
Antimicrobial agents and chemotherapy.
2012 May; 56(5):2397-407. doi:
10.1128/aac.00020-12. [PMID: 22330917] - Shih-Hua Lee, Yu-Ting Liu, Ke-Ming Chen, Chong-Kuei Lii, Cheng-Tzu Liu. Effect of garlic sulfur compounds on neutrophil infiltration and damage to the intestinal mucosa by endotoxin in rats.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2012 Mar; 50(3-4):567-74. doi:
10.1016/j.fct.2011.11.027. [PMID: 22138247] - Małgorzata B Iciek, Danuta Kowalczyk-Pachel, Inga Kwiecień, Magdalena B Dudek. Effects of different garlic-derived allyl sulfides on peroxidative processes and anaerobic sulfur metabolism in mouse liver.
Phytotherapy research : PTR.
2012 Mar; 26(3):425-31. doi:
10.1002/ptr.3572. [PMID: 21815229] - G Dilip Reddy, A Gopala Reddy, G S Rao, M Vijay Kumar. Pharmacokinetic interaction of garlic and atorvastatin in dyslipidemic rats.
Indian journal of pharmacology.
2012 Mar; 44(2):246-52. doi:
10.4103/0253-7613.93860. [PMID: 22529485] - Chong-Kuei Lii, Chun-Yin Huang, Haw-Wen Chen, Mun-Yew Chow, Yu-Ru Lin, Chin-Shiu Huang, Chia-Wen Tsai. Diallyl trisulfide suppresses the adipogenesis of 3T3-L1 preadipocytes through ERK activation.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2012 Mar; 50(3-4):478-84. doi:
10.1016/j.fct.2011.11.020. [PMID: 22137902] - Cheng-Ying Ho, Yu-Ting Cheng, Chi-Fai Chau, Gow-Chin Yen. Effect of diallyl sulfide on in vitro and in vivo Nrf2-mediated pulmonic antioxidant enzyme expression via activation ERK/p38 signaling pathway.
Journal of agricultural and food chemistry.
2012 Jan; 60(1):100-7. doi:
10.1021/jf203800d. [PMID: 22118872] - Melissa L Sokolosky, Michael J Wargovich. Homeostatic imbalance and colon cancer: the dynamic epigenetic interplay of inflammation, environmental toxins, and chemopreventive plant compounds.
Frontiers in oncology.
2012; 2(?):57. doi:
10.3389/fonc.2012.00057. [PMID: 22675672] - Cui-Li Zhang, Tao Zeng, Xiu-Lan Zhao, Li-Hua Yu, Zhen-Ping Zhu, Ke-Qin Xie. Protective effects of garlic oil on hepatocarcinoma induced by N-nitrosodiethylamine in rats.
International journal of biological sciences.
2012; 8(3):363-74. doi:
10.7150/ijbs.3796. [PMID: 22393308] - Ana L Colín-González, Ricardo A Santana, Carlos A Silva-Islas, Maria E Chánez-Cárdenas, Abel Santamaría, Perla D Maldonado. The antioxidant mechanisms underlying the aged garlic extract- and S-allylcysteine-induced protection.
Oxidative medicine and cellular longevity.
2012; 2012(?):907162. doi:
10.1155/2012/907162. [PMID: 22685624] - Ali Mobasheri, Yves Henrotin, Hans-Konrad Biesalski, Mehdi Shakibaei. Scientific evidence and rationale for the development of curcumin and resveratrol as nutraceutricals for joint health.
International journal of molecular sciences.
2012; 13(4):4202-4232. doi:
10.3390/ijms13044202. [PMID: 22605974] - Radu Vasile Bagiu, Brigitha Vlaicu, Monica Butnariu. Chemical composition and in vitro antifungal activity screening of the Allium ursinum L. (Liliaceae).
International journal of molecular sciences.
2012; 13(2):1426-1436. doi:
10.3390/ijms13021426. [PMID: 22408399] - Wenbi Guan, Pengjun Xu, Kai Wang, Yue Song, Hongyan Zhang. Determination and study on dissipation of 1-naphthylacetic acid in garlic and soil using high performance liquid chromatography-tandem mass spectrometry.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Nov; 49(11):2869-74. doi:
10.1016/j.fct.2011.08.009. [PMID: 21864633] - Jasmine George, Madhulika Singh, Amit Kumar Srivastava, Kulpreet Bhui, Yogeshwer Shukla. Synergistic growth inhibition of mouse skin tumors by pomegranate fruit extract and diallyl sulfide: evidence for inhibition of activated MAPKs/NF-κB and reduced cell proliferation.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
2011 Jul; 49(7):1511-20. doi:
10.1016/j.fct.2011.03.040. [PMID: 21443920] - Xiaonan Lu, Barbara A Rasco, Dong Hyun Kang, Jamie M F Jabal, D Eric Aston, Michael E Konkel. Infrared and Raman spectroscopic studies of the antimicrobial effects of garlic concentrates and diallyl constituents on foodborne pathogens.
Analytical chemistry.
2011 Jun; 83(11):4137-46. doi:
10.1021/ac2001498. [PMID: 21553849] - N M Abdel-Hamid, M H Nazmy, A I Abdel-Bakey. Polyol profile as an early diagnostic and prognostic marker in natural product chemoprevention of hepatocellular carcinoma in diabetic rats.
Diabetes research and clinical practice.
2011 May; 92(2):228-37. doi:
10.1016/j.diabres.2011.02.003. [PMID: 21388699] - Mireia Olivan, Sílvia Busquets, Maite Figueras, Cibely Fontes de Oliveira, Míriam Toledo, Angelica Sette, Paula Ventura da Silva, Pablo Barberis, Josep M Argilés, Francisco J López-Soriano. Nutraceutical inhibition of muscle proteolysis: a role of diallyl sulphide in the treatment of muscle wasting.
Clinical nutrition (Edinburgh, Scotland).
2011 Feb; 30(1):33-7. doi:
10.1016/j.clnu.2010.06.004. [PMID: 20655130] - Elizabeth A Mazzio, Fran Close, Karam F A Soliman. The biochemical and cellular basis for nutraceutical strategies to attenuate neurodegeneration in Parkinson's disease.
International journal of molecular sciences.
2011 Jan; 12(1):506-69. doi:
10.3390/ijms12010506. [PMID: 21340000] - Tatsuya Sueyoshi, William D Green, Kellie Vinal, Tyler S Woodrum, Rick Moore, Masahiko Negishi. Garlic extract diallyl sulfide (DAS) activates nuclear receptor CAR to induce the Sult1e1 gene in mouse liver.
PloS one.
2011; 6(6):e21229. doi:
10.1371/journal.pone.0021229. [PMID: 21698271] - Claire M Payne, Cheray Crowley-Skillicorn, Carol Bernstein, Hana Holubec, Harris Bernstein. Molecular and cellular pathways associated with chromosome 1p deletions during colon carcinogenesis.
Clinical and experimental gastroenterology.
2011; 4(?):75-119. doi:
10.2147/ceg.s17114. [PMID: 21753893] - Frances M K Williams, Jane Skinner, Tim D Spector, Aedin Cassidy, Ian M Clark, Rose M Davidson, Alex J MacGregor. Dietary garlic and hip osteoarthritis: evidence of a protective effect and putative mechanism of action.
BMC musculoskeletal disorders.
2010 Dec; 11(?):280. doi:
10.1186/1471-2474-11-280. [PMID: 21143861] - Snowber Yousuf, Aijaz Ahmad, Amber Khan, Nikhat Manzoor, Luqman Ahmad Khan. Effect of diallyldisulphide on an antioxidant enzyme system in Candida species.
Canadian journal of microbiology.
2010 Oct; 56(10):816-21. doi:
10.1139/w10-066. [PMID: 20962904]