Withanolide (BioDeep_00000637440)

Main id: BioDeep_00000007004

Secondary id: BioDeep_00000637441

PANOMIX_OTCML-2023


代谢物信息卡片


(1S,2R,6S,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one

化学式: C28H38O6 (470.2668)
中文名称: 醉茄内酯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC5C6(C4(C(=O)C=CC6O)C)O5)C)O)C
InChI: InChI=1S/C28H38O6/c1-14-12-22(33-24(31)15(14)2)27(5,32)19-7-6-17-16-13-23-28(34-23)21(30)9-8-20(29)26(28,4)18(16)10-11-25(17,19)3/h8-9,16-19,21-23,30,32H,6-7,10-13H2,1-5H3/t16-,17-,18-,19-,21-,22+,23+,25-,26-,27+,28+/m0/s1

描述信息

A withanolide that is 5,6:22,26-diepoxyergosta-2,24-diene-1,26-dione substituted by hydroxy groups at positions 4 and 22 (the 4beta,5beta,6beta,22R stereoisomer). Isolated from Tubocapsicum anomalum and Withania somnifera, it exhibits cytotoxic activity.
Withanolides, which are extracted from Withania somnifera, are employed in the treatment of arthritis and are known to be potent inhibitors of angiogenesis, inflammation and oxidative stress. Withanolides can indeed inhibit the activation of NF-κB and NF-κB-regulated gene expression, which could explain their anti-arthritic actions. W. somnifera root powder has suppressive effect on arthritis by reducing amplification and propagation of the inflammatory response, without causing any gastric damage. (PMID: 17475558, 3248848, 17084827) [HMDB]

同义名列表

5 个代谢物同义名

Withanolide D; Withanolide; (1S,2R,6S,9R,11S,12S,15S,16S)-15-[(1R)-1-[(2R)-4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-hydroxyethyl]-6-hydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.0^{2,7}.0^{7,9}.0^{12,16}]octadec-4-en-3-one; ST 28:6;O6; Withanolide D



数据库引用编号

17 个数据库交叉引用编号

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

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。

亚细胞结构定位 关联基因列表
Cytoplasm 14 ABCB1, ANXA5, BDNF, CTNNB1, MAPK14, MAPK8, NTRK2, PIK3CA, RAC1, RAD51, SMPD3, TLR2, TLR4, TP53BP1
Peripheral membrane protein 3 ACHE, ANXA5, CYP1B1
Endosome membrane 2 NTRK2, TLR4
Endoplasmic reticulum membrane 2 CYP1B1, RAC1
Nucleus 8 ACHE, CTNNB1, MAPK14, MAPK8, RAC1, RAD51, TP53BP1, XRCC4
cytosol 9 ANXA5, CTNNB1, MAPK14, MAPK8, NTRK2, PIK3CA, RAC1, RAD51, XRCC4
dendrite 4 BDNF, DRD2, NTRK2, RAC1
nuclear body 1 TP53BP1
trans-Golgi network 1 RAC1
centrosome 2 CTNNB1, RAD51
nucleoplasm 6 CTNNB1, MAPK14, MAPK8, RAD51, TP53BP1, XRCC4
Cell membrane 10 ABCB1, ACHE, CTNNB1, DRD2, NTRK2, RAC1, SMPD2, SMPD3, TLR4, TNF
Lipid-anchor 2 RAC1, SMPD3
Cytoplasmic side 1 RAC1
lamellipodium 3 CTNNB1, PIK3CA, RAC1
ruffle membrane 1 RAC1
Cell projection, axon 1 NTRK2
Early endosome membrane 1 NTRK2
Multi-pass membrane protein 3 ABCB1, DRD2, SMPD2
Golgi apparatus membrane 2 DRD2, SMPD3
Synapse 5 ACHE, CTNNB1, DRD2, MAPK8, RAC1
cell cortex 2 CTNNB1, RAC1
cell junction 1 CTNNB1
cell surface 5 ABCB1, ACHE, TLR2, TLR4, TNF
glutamatergic synapse 4 CTNNB1, DRD2, MAPK14, RAC1
Golgi apparatus 2 ACHE, TLR2
Golgi membrane 2 DRD2, SMPD3
neuromuscular junction 1 ACHE
neuronal cell body 1 TNF
postsynapse 1 RAC1
presynaptic membrane 2 CTNNB1, DRD2
sarcolemma 1 ANXA5
synaptic vesicle 1 BDNF
acrosomal vesicle 1 DRD2
plasma membrane 12 ABCB1, ACHE, CTNNB1, DRD2, NTRK2, PIK3CA, RAC1, SMPD2, SMPD3, TLR2, TLR4, TNF
synaptic vesicle membrane 1 DRD2
terminal bouton 1 NTRK2
Membrane 11 ABCB1, ACHE, ANXA5, BDNF, CTNNB1, CYP1B1, NTRK2, RAC1, SMPD3, TLR2, TLR4
apical plasma membrane 1 ABCB1
axon 4 BDNF, DRD2, MAPK8, NTRK2
basolateral plasma membrane 1 CTNNB1
caveola 1 SMPD2
extracellular exosome 4 ABCB1, ANXA5, CTNNB1, RAC1
endoplasmic reticulum 1 SMPD2
extracellular space 3 ACHE, BDNF, TNF
perinuclear region of cytoplasm 7 ACHE, BDNF, CTNNB1, NTRK2, PIK3CA, RAD51, TLR4
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
intercalated disc 1 PIK3CA
mitochondrion 3 CYP1B1, MAPK14, RAD51
protein-containing complex 2 CTNNB1, RAD51
intracellular membrane-bounded organelle 1 CYP1B1
Microsome membrane 1 CYP1B1
postsynaptic density 1 NTRK2
Single-pass type I membrane protein 3 NTRK2, TLR2, TLR4
Secreted 3 ACHE, BDNF, RAC1
extracellular region 7 ACHE, ANXA5, BDNF, MAPK14, RAC1, SMPD3, TNF
Mitochondrion matrix 1 RAD51
mitochondrial matrix 1 RAD51
Extracellular side 1 ACHE
transcription regulator complex 1 CTNNB1
ciliary membrane 1 DRD2
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 RAD51
external side of plasma membrane 3 ANXA5, TLR4, TNF
dendritic spine 3 DRD2, NTRK2, RAC1
perikaryon 1 DRD2
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
cytoplasmic vesicle 1 RAC1
nucleolus 1 RAD51
Wnt signalosome 1 CTNNB1
Early endosome 2 NTRK2, TLR4
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 2 CTNNB1, DRD2
Apical cell membrane 1 ABCB1
Cell projection, lamellipodium 1 RAC1
Cytoplasm, perinuclear region 1 NTRK2
Membrane raft 2 TLR2, TNF
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 3 ANXA5, CTNNB1, RAC1
GABA-ergic synapse 1 DRD2
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
basement membrane 1 ACHE
PML body 1 RAD51
collagen-containing extracellular matrix 1 ANXA5
fascia adherens 1 CTNNB1
lateral plasma membrane 2 CTNNB1, DRD2
nuclear speck 1 MAPK14
Cell projection, ruffle 1 TLR4
ruffle 1 TLR4
receptor complex 3 NTRK2, TLR2, TLR4
Zymogen granule membrane 1 ANXA5
cilium 1 DRD2
chromatin 1 RAD51
Cytoplasmic vesicle, phagosome membrane 1 TLR2
cell projection 1 TLR2
phagocytic cup 2 TLR4, TNF
phagocytic vesicle membrane 1 TLR2
cell periphery 2 CTNNB1, SMPD2
Chromosome 3 RAD51, TP53BP1, XRCC4
cytoskeleton 1 RAC1
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
cytoplasmic ribonucleoprotein granule 1 RAC1
spindle pole 2 CTNNB1, MAPK14
chromosome, telomeric region 2 RAD51, TP53BP1
nuclear chromosome 1 RAD51
non-motile cilium 1 DRD2
postsynaptic density, intracellular component 1 CTNNB1
Lipid-anchor, GPI-anchor 1 ACHE
microvillus membrane 1 CTNNB1
site of double-strand break 3 RAD51, TP53BP1, XRCC4
sperm flagellum 1 DRD2
Recycling endosome membrane 1 RAC1
Endomembrane system 1 CTNNB1
Chromosome, centromere, kinetochore 1 TP53BP1
lateral element 1 RAD51
Cell projection, dendrite 2 NTRK2, RAC1
Melanosome 1 RAC1
euchromatin 1 CTNNB1
cell body 1 TLR2
side of membrane 1 ACHE
replication fork 1 TP53BP1
lipopolysaccharide receptor complex 1 TLR4
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
secretory granule membrane 2 RAC1, TLR2
endoplasmic reticulum lumen 1 BDNF
male germ cell nucleus 1 RAD51
axon terminus 2 DRD2, NTRK2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
kinetochore 1 TP53BP1
endocytic vesicle 1 DRD2
beta-catenin-TCF complex 1 CTNNB1
condensed nuclear chromosome 1 RAD51
presynaptic active zone cytoplasmic component 1 CTNNB1
vesicle membrane 1 ANXA5
synaptic cleft 1 ACHE
protein-DNA complex 1 CTNNB1
ficolin-1-rich granule membrane 1 RAC1
external side of apical plasma membrane 1 ABCB1
basal dendrite 1 MAPK8
dopaminergic synapse 1 DRD2
condensed chromosome 1 RAD51
DNA repair complex 1 TP53BP1
Toll-like receptor 1-Toll-like receptor 2 protein complex 1 TLR2
Toll-like receptor 2-Toll-like receptor 6 protein complex 1 TLR2
catenin complex 1 CTNNB1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
NADPH oxidase complex 1 RAC1
presynaptic intermediate filament cytoskeleton 1 RAD51
endothelial microparticle 1 ANXA5
DNA-dependent protein kinase-DNA ligase 4 complex 1 XRCC4
nonhomologous end joining complex 1 XRCC4
G protein-coupled receptor complex 1 DRD2
beta-catenin-TCF7L2 complex 1 CTNNB1
[Isoform H]: Cell membrane 1 ACHE
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
nuclear ubiquitin ligase complex 1 RAD51
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
DNA ligase IV complex 1 XRCC4
Golgi cis cisterna 1 SMPD3
[Protein XRCC4, C-terminus]: Cytoplasm 1 XRCC4
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Md Abdul Hannan, Raju Dash, Md Nazmul Haque, Sung Min Choi, Il Soo Moon. Integrated System Pharmacology and In Silico Analysis Elucidating Neuropharmacological Actions of Withania somnifera in the Treatment of Alzheimer's Disease. CNS & neurological disorders drug targets. 2020; 19(7):541-556. doi: 10.2174/1871527319999200730214807. [PMID: 32748763]
  • Mahendra Kumar Trivedi, Parthasarathi Panda, Kalyan Kumar Sethi, Snehasis Jana. Metabolite Profiling in Withania somnifera Roots Hydroalcoholic Extract Using LC/MS, GC/MS and NMR Spectroscopy. Chemistry & biodiversity. 2017 Mar; 14(3):. doi: 10.1002/cbdv.201600280. [PMID: 27743505]
  • Sayantani Sarkar, Chandan Mandal, Rajender Sangwan, Chitra Mandal. Coupling G2/M arrest to the Wnt/β-catenin pathway restrains pancreatic adenocarcinoma. Endocrine-related cancer. 2014 Feb; 21(1):113-25. doi: 10.1530/erc-13-0315. [PMID: 24402132]
  • Amreen A Siddique, Pallavi Joshi, Laxminarain Misra, Neelam S Sangwan, Mahendra P Darokar. 5,6-de-epoxy-5-en-7-one-17-hydroxy withaferin A, a new cytotoxic steroid from Withania somnifera L. Dunal leaves. Natural product research. 2014; 28(6):392-8. doi: 10.1080/14786419.2013.871545. [PMID: 24422976]
  • Vincent Roumy, Murielle Biabiany, Thierry Hennebelle, El Moukhtar Aliouat, Muriel Pottier, Henry Joseph, Sami Joha, Bruno Quesnel, Racha Alkhatib, Sevser Sahpaz, François Bailleul. Antifungal and cytotoxic activity of withanolides from Acnistus arborescens. Journal of natural products. 2010 Jul; 73(7):1313-7. doi: 10.1021/np100201p. [PMID: 20590148]
  • Claudia P Cordero, Sandra J Morantes, Alexandra Páez, Javier Rincón, Fabio A Aristizábal. Cytotoxicity of withanolides isolated from Acnistus arborescens. Fitoterapia. 2009 Sep; 80(6):364-8. doi: 10.1016/j.fitote.2009.05.011. [PMID: 19460421]
  • Maumita Bandyopadhyay, Sumita Jha, David Tepfer. Changes in morphological phenotypes and withanolide composition of Ri-transformed roots of Withania somnifera. Plant cell reports. 2007 May; 26(5):599-609. doi: 10.1007/s00299-006-0260-0. [PMID: 17103214]
  • Pei-Wen Hsieh, Zih-You Huang, Jyun-Hong Chen, Fang-Rong Chang, Ching-Chung Wu, Yu-Liang Yang, Michael Y Chiang, Ming-Hon Yen, Shu-Li Chen, Hsin-Fu Yen, Tilo Lübken, Wen-Chun Hung, Yang-Chang Wu. Cytotoxic withanolides from Tubocapsicum anomalum. Journal of natural products. 2007 May; 70(5):747-53. doi: 10.1021/np0605541. [PMID: 17417907]
  • Paola Bargagna-Mohan, Padma Priya Ravindranath, Royce Mohan. Small molecule anti-angiogenic probes of the ubiquitin proteasome pathway: potential application to choroidal neovascularization. Investigative ophthalmology & visual science. 2006 Sep; 47(9):4138-45. doi: 10.1167/iovs.05-1452. [PMID: 16936134]
  • Emma Maldonado, Fernando R Torres, Mahinda Martínez, Ana L Pérez-Castorena. 18-Acetoxywithanolides from Physalis chenopodifolia1. Planta medica. 2004 Jan; 70(1):59-64. doi: 10.1055/s-2004-815457. [PMID: 14765295]
  • M Ganzera, M I Choudhary, I A Khan. Quantitative HPLC analysis of withanolides in Withania somnifera. Fitoterapia. 2003 Feb; 74(1-2):68-76. doi: 10.1016/s0367-326x(02)00325-8. [PMID: 12628397]
  • S Ray, S Jha. Production of withaferin A in shoot cultures of Withania somnifera. Planta medica. 2001 Jul; 67(5):432-6. doi: 10.1055/s-2001-15811. [PMID: 11488457]