Tryptophol (BioDeep_00000001223)

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019

代谢物信息卡片

3-(2-Hydroxyethyl)-1H-indole

化学式: C10H11NO (161.0840596)
中文名称: 色醇, 3-(2-羟乙基)吲哚
谱图信息: 最多检出来源 Homo sapiens(blood) 0.09%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Tryptophol. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/tryptophol (retrieved 2024-11-10) (BioDeep RN: BioDeep_00000001223). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CN2)CCO
InChI: InChI=1S/C10H11NO/c12-6-5-8-7-11-10-4-2-1-3-9(8)10/h1-4,7,11-12H,5-6H2

描述信息

Tryptophol, also known as indole-3-ethanol, is an indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. It has a role as a Saccharomyces cerevisiae metabolite, an auxin and a plant metabolite. Tryptophol is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine (PMID:30120222). Tryptophol production was negatively associated with interferon-gamma production (IFNγ) which suggests that tryptophol has anti-inflammatory properties (PMID:27814509). Tryptophol has also been identified as the hypnotic agent in trypanosomal sleeping sickness, and because it is formed in vivo after ethanol or disulfiram treatment, it is also associated with the study of alcoholism (PMID:7241135).
Indole-3-ethanol is a dietary indole present in cruciferous vegetables that has been shown to influence estradiol metabolism in humans and may provide a new chemopreventive approach to estrogen-dependent diseases. (PMID 2342128)

Tryptophol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=526-55-6 (retrieved 2024-06-29) (CAS RN: 526-55-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Tryptophol (Indole-3-ethanol) is an endogenous metabolite.
Tryptophol (Indole-3-ethanol) is an endogenous metabolite.

同义名列表

27 个代谢物同义名

3-(2-Hydroxyethyl)-1H-indole; 3-(beta-Hydroxyethyl)indole; 2-(1H-indol-3-yl)ethan-1-ol; 3-(2-Hydroxyethyl)indole; 3-(b-Hydroxyethyl)indole; 3-(β-Hydroxyethyl)indole; 2-(1H-indol-3-yl)Ethanol; beta-indol-3-Ylethanol; beta-(3-Indole)ethanol; 2-(indol-3-yl)Ethanol; 2-(3-Indolyl)ethanol; 1H-Indolyl-3-ethanol; 1H-Indole-3-ethanol; b-(3-Indole)ethanol; 2-(3-Indolylethanol; β-(3-Indole)ethanol; Indole-3-ethanol; 3-Indolylethanol; 3-Indole ethanol; 3-Indoleethanol; DL-Tryptophanol; Indole ethanol; Indoleethanol; Tryptophanol; Tryptophol; IEA; Tryptophanol

数据库引用编号

24 个数据库交叉引用编号

ChEBI: CHEBI:17890
KEGG: C00955
PubChem: 10685
HMDB: HMDB0003447
Metlin: METLIN6932
ChEMBL: CHEMBL226545
Wikipedia: Tryptophol
MetaCyc: CPD-341
KNApSAcK: C00000114
foodb: FDB010973
chemspider: 10235
CAS: 526-55-6
MoNA: KO001201
MoNA: KO001205
MoNA: KO001204
MoNA: KO001203
MoNA: KO001202
PMhub: MS000000161
PDB-CCD: ZCW
3DMET: B00207
NIKKAJI: J6.661C
RefMet: Tryptophanol
medchemexpress: HY-W010155
BioNovoGene_Lab2019: BioNovoGene_Lab2019-418

分类词条

代谢反应

10 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(8)

tryptophan degradation via tryptamine: H₂O + O₂ + tryptamine ⟶ (indol-3-yl)acetaldehyde + ammonium + hydrogen peroxide
superpathway of tryptophan utilization: N-formylkynurenine + H₂O ⟶ H⁺ + L-kynurenine + formate
L-tryptophan degradation V (side chain pathway): NAD(P)⁺ + indole-3-ethanol ⟶ (indol-3-yl)acetaldehyde + H⁺ + NAD(P)H
L-tryptophan degradation X (mammalian, via tryptamine): (indol-3-yl)acetaldehyde + H⁺ + NADPH ⟶ NADP⁺ + indole-3-ethanol
L-tryptophan degradation VIII (to tryptophol): NAD⁺ + indole-3-ethanol ⟶ (indol-3-yl)acetaldehyde + H⁺ + NADH
tryptophan degradation VIII (to tryptophol): 2-oxoglutarate + trp ⟶ (indol-3-yl)pyruvate + glu
tryptophan degradation X (mammalian, via tryptamine): H₂O + O₂ + tryptamine ⟶ H⁺ + ammonia + hydrogen peroxide + indole acetaldehyde
tryptophan degradation: α-ketoglutarate + L-tryptophan ⟶ L-glutamate + indolepyruvate

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(2)

alpha-Linolenic Acid Metabolism: -Linolenic acid + Oxygen ⟶ 13(S)-HPOTE
Tryptophan Metabolism: N'-Formylkynurenine + Water ⟶ Formic acid + Hydrogen Ion + L-Kynurenine

PharmGKB(0)

21 个相关的物种来源信息

7461 - Apis cerana: 10.1371/JOURNAL.PONE.0175573
51584 - Balansia epichloe: 10.1016/S0031-9422(00)81037-7
5476 - Candida albicans: 10.1126/SCIENCE.163.3863.192
318705 - Curvularia nodulosa: 10.1016/S0031-9422(00)81810-5
53862 - Dalbergia: 10.1016/S0031-9422(00)81407-7
196648 - Desmanthus illinoensis: 10.1021/JF00075A020
3039 - Euglena gracilis: 10.3389/FBIOE.2021.662655
226899 - Grosmannia clavigera: 10.1139/V86-149
5161 - Grosmannia crassivaginata: 10.1016/0031-9422(94)00630-C
4232 - Helianthus annuus: 10.1111/J.1399-3054.1967.TB07207.X
9606 - Homo sapiens: -
1336870 - Luffariella geometrica: 10.1021/NP010544U
1302847 - Mucor moelleri: 10.1016/S0953-7562(09)80999-4
1406 - Paenibacillus polymyxa: 10.1111/J.1574-6941.1997.TB00384.X
565426 - Paraphaeosphaeria minitans: 10.1016/S0031-9422(01)00129-7
4837 - Phycomyces blakesleeanus: 10.1111/J.1399-3054.1987.TB01951.X
3329 - Picea abies: 10.1093/TREEPHYS/3.2.185
3349 - Pinus sylvestris:
66869 - Streptomyces atroolivaceus:
67332 - Streptomyces mutabilis:
29760 - Vitis vinifera: 10.3389/FMICB.2017.00457

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

Kumudini M Meepagala, Caleb M Anderson, Natascha Techen, Stephen O Duke. Pantoea ananatis, a plant growth stimulating bacterium, and its metabolites isolated from Hydrocotyle umbellata (dollarweed). Plant signaling & behavior. 2024 Dec; 19(1):2331894. doi: 10.1080/15592324.2024.2331894. [PMID: 38516998]
Jing Zhou, Huiling Wei, Shu-Ming Li. Colletotriauxins A-D, New Plant Growth Inhibitors from the Phytopathogenic Fungus Colletotrichum gloeosporioides. Journal of agricultural and food chemistry. 2023 Jul; ?(?):. doi: 10.1021/acs.jafc.3c03143. [PMID: 37434536]
Rosiane Dos Santos, Raquel P Morais-Urano, Rosilene M Marçal, Geraldo H Silva, Mário F C Santos. Acetylcholinesterase and butyrylcholinesterase inhibition by nectriapyrone and tryptophol isolated from endophytic fungus Phomopsis sp. Natural product research. 2022 Aug; 36(16):4153-4158. doi: 10.1080/14786419.2021.1960327. [PMID: 34498969]
Yueqin Fan, Kefei Yu, Huabao Zheng, Yinyan Chen, Ruojin Zhao, Yiyi Li, Zhanwang Zheng. A high-yielding strain of indole-3-acetic acid isolated from food waste compost: metabolic pathways, optimization of fermentation conditions, and application. Environmental technology. 2022 Jun; ?(?):1-11. doi: 10.1080/09593330.2022.2082889. [PMID: 35678156]
Jiahui Shao, Yucong Li, Zunfeng Li, Zhihui Xu, Weibing Xun, Nan Zhang, Haichao Feng, Youzhi Miao, Qirong Shen, Ruifu Zhang. Participating mechanism of a major contributing gene ysnE for auxin biosynthesis in Bacillus amyloliquefaciens SQR9. Journal of basic microbiology. 2021 Jun; 61(6):569-575. doi: 10.1002/jobm.202100098. [PMID: 33914927]
Antonio Ruiz-Gonzalez, Adam J Clancy, Kwang-Leong Choy. Rapid detection of free and bound toxins using molecularly imprinted silica/graphene oxide hybrids. Chemical communications (Cambridge, England). 2021 Apr; 57(33):4043-4046. doi: 10.1039/d1cc00572c. [PMID: 33885678]
Hardik Naik Jinal, Krishnan Sakthivel, Natarajan Amaresan. Characterisation of antagonistic Bacillus paralicheniformis (strain EAL) by LC-MS, antimicrobial peptide genes, and ISR determinants. Antonie van Leeuwenhoek. 2020 Aug; 113(8):1167-1177. doi: 10.1007/s10482-020-01423-4. [PMID: 32410087]
Lulu Shao, Ping Wu, Liangxiong Xu, Jinghua Xue, Hanxiang Li, Xiaoyi Wei. Colletotryptins A-F, new dimeric tryptophol derivatives from the endophytic fungus Colletotrichum sp. SC1355. Fitoterapia. 2020 Mar; 141(?):104465. doi: 10.1016/j.fitote.2019.104465. [PMID: 31870947]
Kun Luo, Caro-Lyne DesRoches, Anne Johnston, Linda J Harris, Hui-Yan Zhao, Thérèse Ouellet. Multiple metabolic pathways for metabolism of l-tryptophan in Fusarium graminearum. Canadian journal of microbiology. 2017 Nov; 63(11):921-927. doi: 10.1139/cjm-2017-0383. [PMID: 28926717]
M Soledade C Pedras, Vijay K Sarma-Mamillapalle. Metabolism and metabolites of dithiocarbamates in the plant pathogenic fungus Leptosphaeria maculans. Journal of agricultural and food chemistry. 2012 Aug; 60(32):7792-8. doi: 10.1021/jf302038a. [PMID: 22823278]
Md Mujahid, Ch Sasikala, Ch V Ramana. Aniline-induced tryptophan production and identification of indole derivatives from three purple bacteria. Current microbiology. 2010 Oct; 61(4):285-90. doi: 10.1007/s00284-010-9609-2. [PMID: 20852980]
Laura J Quittenden, Noel W Davies, Jason A Smith, Peter P Molesworth, Nathan D Tivendale, John J Ross. Auxin biosynthesis in pea: characterization of the tryptamine pathway. Plant physiology. 2009 Nov; 151(3):1130-8. doi: 10.1104/pp.109.141507. [PMID: 19710233]
Véronique Chagué, Rudy Maor, Amir Sharon. CgOpt1, a putative oligopeptide transporter from Colletotrichum gloeosporioides that is involved in responses to auxin and pathogenicity. BMC microbiology. 2009 Aug; 9(?):173. doi: 10.1186/1471-2180-9-173. [PMID: 19698103]
Hexon Angel Contreras-Cornejo, Lourdes Macías-Rodríguez, Carlos Cortés-Penagos, José López-Bucio. Trichoderma virens, a plant beneficial fungus, enhances biomass production and promotes lateral root growth through an auxin-dependent mechanism in Arabidopsis. Plant physiology. 2009 Mar; 149(3):1579-92. doi: 10.1104/pp.108.130369. [PMID: 19176721]
Ivan Kosalec, Olivier Puel, Marcel Delaforge, Nevenka Kopjar, Roberto Antolovic, Dubravko Jelic, Biserka Matica, Pierre Galtier, Stjepan Pepeljnjak. Isolation and cytotoxicity of low-molecular-weight metabolites of Candida albicans. Frontiers in bioscience : a journal and virtual library. 2008 May; 13(?):6893-904. doi: 10.2741/3197. [PMID: 18508703]
Mandira Malhotra, Sheela Srivastava. An ipdC gene knock-out of Azospirillum brasilense strain SM and its implications on indole-3-acetic acid biosynthesis and plant growth promotion. Antonie van Leeuwenhoek. 2008 May; 93(4):425-33. doi: 10.1007/s10482-007-9207-x. [PMID: 17952626]
Shyuichiro Inagaki, Shigeru Morimura, Kazunobu Gondo, Yueqin Tang, Hiroshi Akutagawa, Kenji Kida. Isolation of tryptophol as an apoptosis-inducing component of vinegar produced from boiled extract of black soybean in human monoblastic leukemia U937 cells. Bioscience, biotechnology, and biochemistry. 2007 Feb; 71(2):371-9. doi: 10.1271/bbb.60336. [PMID: 17284845]
M Soledade C Pedras, Mukund Jha. Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin. Bioorganic & medicinal chemistry. 2006 Jul; 14(14):4958-79. doi: 10.1016/j.bmc.2006.03.014. [PMID: 16616505]
Matthew A Churchward, R Hussain Butt, John C Lang, Kimberly K Hsu, Jens R Coorssen. Enhanced detergent extraction for analysis of membrane proteomes by two-dimensional gel electrophoresis. Proteome science. 2005 Jun; 3(1):5. doi: 10.1186/1477-5956-3-5. [PMID: 15941475]
Olivier Vandeputte, Sevgi Oden, Adeline Mol, Danny Vereecke, Koen Goethals, Mondher El Jaziri, Els Prinsen. Biosynthesis of auxin by the gram-positive phytopathogen Rhodococcus fascians is controlled by compounds specific to infected plant tissues. Applied and environmental microbiology. 2005 Mar; 71(3):1169-77. doi: 10.1128/aem.71.3.1169-1177.2005. [PMID: 15746315]
Kuang Ren Chung, Turksen Shilts, Umran Ertürk, L W Timmer, Peter P Ueng. Indole derivatives produced by the fungus Colletotrichum acutatum causing lime anthracnose and postbloom fruit drop of citrus. FEMS microbiology letters. 2003 Sep; 226(1):23-30. doi: 10.1016/s0378-1097(03)00605-0. [PMID: 13129603]
Q Yue, C J Miller, J F White, M D Richardson. Isolation and characterization of fungal inhibitors from Epichloë festucae. Journal of agricultural and food chemistry. 2000 Oct; 48(10):4687-92. doi: 10.1021/jf990685q. [PMID: 11052720]
J E Hall, J R Seed. Increased urinary excretion of aromatic amino acid catabolites by Microtus montanus chronically infected with Trypanosoma brucei gambiense. Comparative biochemistry and physiology. B, Comparative biochemistry. 1984; 77(4):755-60. doi: 10.1016/0305-0491(84)90309-2. [PMID: 6375946]
A Moshtaghfard, I Smith. Acyltryptophols reversibly inhibit the uptake of thymidine after phytohaemagglutinin transformation of human lymphocytes. Journal of neural transmission. 1983; 56(1):43-52. doi: 10.1007/bf01243373. [PMID: 6854309]
E M Cornford, P D Crane, L D Braun, W D Bocash, A M Nyerges, W H Oldendorf. Reduction in brain glucose utilization rate after tryptophol (3-indole ethanol) treatment. Journal of neurochemistry. 1981 May; 36(5):1758-65. doi: 10.1111/j.1471-4159.1981.tb00428.x. [PMID: 7241135]
E M Cornford, W D Bocash, L D Braun, P D Crane, W H Oldendorf, A J MacInnis. Rapid distribution of tryptophol (3-indole ethanol) to the brain and other tissues. The Journal of clinical investigation. 1979 Jun; 63(6):1241-8. doi: 10.1172/jci109419. [PMID: 447842]