Chrysophanic acid (BioDeep_00000398597)

PANOMIX_OTCML-2023 Volatile Flavor Compounds

代谢物信息卡片

Chrysophanic acid

化学式: C15H10O4 (254.057906)
中文名称: 大黄酚
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=CC(=C2C(=C1)C(=O)C3=C(C2=O)C(=CC=C3)O)O
InChI: InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3

描述信息

relative retention time with respect to 9-anthracene Carboxylic Acid is 1.321
D009676 - Noxae > D009153 - Mutagens
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.322
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.318
relative retention time with respect to 9-anthracene Carboxylic Acid is 1.324
Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K.
Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K.

同义名列表

3 个代谢物同义名

Chrysophanic acid; Chrysophanol; Chrysophanol

数据库引用编号

17 个数据库交叉引用编号

ChEBI: CHEBI:3687
PubChem: 10208
ChEMBL: CHEMBL41092
CAS: 481-74-3
MoNA: BML80948
MoNA: BML80947
MoNA: BML80946
MoNA: BML80945
MoNA: BML01181
MoNA: BML01172
MoNA: BML01163
MoNA: BML01132
MoNA: BML01120
medchemexpress: HY-13595
KEGG: C10315
PubChem: 12501
KNApSAcK: 3687

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)

205 个相关的物种来源信息

2182550 - Abrus melanospermus: 10.1055/S-2007-971214
102750 - Ageratina altissima: 10.1515/ZNB-2005-0916
25641 - Aloe: 10.1002/JPS.2600580211
1389490 - Aloe aculeata: 10.1016/S0031-9422(00)94771-X
45385 - Aloe arborescens:
48875 - Aloe bakeri:
1331516 - Aloe broomii: 10.1016/S0176-1617(11)81144-2
1813110 - Aloe calidophila: 10.1016/S0031-9422(00)94771-X
1593063 - Aloe camperi: 10.1016/S0031-9422(00)94771-X
1389495 - Aloe castellorum: 10.1080/14786410802242851
1188283 - Aloe chabaudii: 10.1016/S0031-9422(00)94771-X
1593069 - Aloe debrana:
1813113 - Aloe elgonica: 10.1016/S0176-1617(11)81144-2
1389501 - Aloe ellenbeckii: 10.1016/S0031-9422(00)94771-X
117798 - Aloe ferox: 10.1016/S0176-1617(11)81144-2
1128790 - Aloe globuligemma:
1128792 - Aloe greatheadii: 10.1016/S0031-9422(00)94771-X
1389509 - Aloe harlana: 10.1016/S0031-9422(00)94771-X
247124 - Aloe humilis: 10.1016/S0176-1617(11)81144-2
1593082 - Aloe khamiesensis: 10.1016/0305-1978(94)90102-3
1389513 - Aloe kilifiensis: 10.1016/S0031-9422(00)94771-X
1593086 - Aloe lateritia: 10.1016/S0031-9422(00)94771-X
212387 - Aloe macra: 10.1016/0305-1978(95)00063-1
1593091 - Aloe macrocarpa: 10.1016/S0031-9422(00)94771-X
1155789 - Aloe maculata:
1389516 - Aloe megalacantha: 10.1016/S0031-9422(00)94771-X
117806 - Aloe nyeriensis: 10.1016/S0176-1617(11)81144-2
210981 - Aloe occidentalis: 10.1016/0305-1978(95)00063-1
49726 - Aloe purpurea: 10.1016/0305-1978(95)00063-1
1811902 - Aloe rivae:
1593106 - Aloe schelpei: 10.1016/S0031-9422(00)94771-X
1593107 - Aloe secundiflora: 10.1016/S0031-9422(00)94771-X
1593109 - Aloe sinana: 10.1016/S0031-9422(00)94771-X
1128810 - Aloe succotrina:
1389527 - Aloe trichosantha: 10.1016/S0031-9422(00)94771-X
1331519 - Aloe vaombe: 10.1016/0305-1978(94)90102-3
34199 - Aloe vera:
1593115 - Aloe volkensii: 10.1016/S0176-1617(11)81144-2
888276 - Aloidendron dichotomum: 10.1016/S0176-1617(11)81144-2
2686335 - Alvaradoa haitiensis:
2686329 - Alvaradoa jamaicensis:
714442 - Ampelopsis Japonica: -
184783 - Areca Catechu L.: -
35608 - Artemisia annua: 10.1016/S0278-6915(99)00027-7
180472 - Asahinea chrysantha: 10.1007/BF00638766
1133552 - Asphodeline damascena: 10.1016/0031-9422(85)80028-5
49696 - Asphodeline lutea: 10.1007/S10600-010-9604-7
2269067 - Asphodeline taurica: 10.1016/0031-9422(89)80076-7
49698 - Asphodelus aestivus: 10.1016/S0031-9422(00)90193-6
207931 - Asphodelus albus: 10.1055/S-0028-1097723
1497607 - Asphodelus fistulosus:
1423376 - Asphodelus tenuifolius: 10.1016/S0031-9422(00)90193-6
314325 - Aster sedifolius: 10.1016/S0031-9422(98)00354-9
588669 - Aster tataricus: 10.1016/S0031-9422(98)00354-9
1226760 - Berchemia floribunda: 10.1248/CPB.56.1248
749552 - Boeremia foveata: 10.1042/BJ0980112
2511937 - Bulbine abyssinica: 10.1016/J.TET.2005.01.040
53852 - Cassia fistula:
162709 - Cassia grandis:
508996 - Cassia javanica:
1231245 - Cassia renigera:
948717 - Cassia roxburghii:
38033 - Chaetomium globosum: 10.1055/S-2002-34415
948715 - Chamaecrista mimosoides: 10.1055/S-2007-969598
1526916 - Chamaecrista pumila: 10.1016/S0367-326X(99)00041-6
103745 - Chromolaena odorata: 10.1515/ZNB-2005-0916
13427 - Cichorium intybus: 10.1016/S0278-6915(99)00027-7
392618 - Cunila: 10.1007/S00299-018-2303-8
117953 - Dendrobium fimbriatum: 10.5530/PJ.2014.3.6
117978 - Dendrobium thyrsiflorum: 10.1016/J.PHYTOCHEM.2005.04.001
52152 - Elymus repens: 10.1016/S0278-6915(99)00027-7
142771 - Entodon luridus: 10.4268/CJCMM20161809
928054 - Eremurus chinensis: 10.1021/NP9904915
526195 - Euphorbia hylonoma: 10.1016/J.FITOTE.2006.09.019
3617 - Fagopyrum esculentum: 10.1016/S0278-6915(99)00027-7
76025 - Fallopia multiflora: 10.1002/PTR.2358
198768 - Harungana madagascariensis:
34190 - Hemerocallis fulva: 10.3109/13880209009082803
106683 - Karwinskia humboldtiana: 10.1016/S0031-9422(00)88492-7
555898 - Kniphofia caulescens: 10.1016/0305-1978(88)90089-0
555937 - Kniphofia ensifolia: 10.1016/J.BMC.2013.11.032
214838 - Kniphofia foliosa:
214840 - Kniphofia insignis: 10.1016/0031-9422(86)80014-0
214841 - Kniphofia isoetifolia: 10.1016/0031-9422(86)80014-0
555912 - Kniphofia linearifolia: 10.1016/0305-1978(88)90089-0
214842 - Kniphofia pumila: 10.1016/0031-9422(86)80014-0
214843 - Kniphofia schimperi: 10.1016/0031-9422(86)80014-0
4236 - Lactuca sativa: 10.1016/S0278-6915(99)00027-7
2689076 - Ligusticum chuanxiong: 10.4268/CJCMM20111013
2689076 - Ligusticum chuanxiong Hort.: -
1508160 - Ligusticum striatum: 10.4268/CJCMM20111013
106689 - Maesopsis eminii: 10.1055/S-2007-969586
38448 - Monilinia fructicola:
71662 - Monodictys: 10.1248/CPB.55.1097
424903 - Osmanthus armatus: 10.1080/14786410802689713
217990 - Phormium cookianum: 10.1021/NP50052A039
51475 - Phormium tenax: 10.1021/NP50052A039
1129486 - Picramnia antidesma:
2686326 - Picramnia hirsuta:
681474 - Picramnia latifolia:
2686319 - Picramnia sellowii: 10.1021/NP070560C
3888 - Pisum sativum: 10.1016/S0278-6915(99)00027-7
101996 - Plantago coronopus: 10.1016/S0278-6915(99)00027-7
39414 - Plantago lanceolata: 10.1016/S0278-6915(99)00027-7
33090 - Plants: -
158314 - Polyporus umbellatus: 10.1007/S10600-009-9229-X
999591 - Psorospermum febrifugum: 10.1016/0031-9422(83)83041-6
139234 - Pyrenophora catenaria: 10.1016/S0031-9422(00)91370-0
438378 - Ramularia uredinicola: 10.1021/NP800138Y
3610 - Rhamnus cathartica:
105902 - Rhamnus davurica: 10.1021/NP010030V
1813053 - Rhamnus formosana: 10.1016/0031-9422(90)85356-K
1813059 - Rhamnus kurdica: 10.3109/13880209209053982
1813207 - Rhamnus nakaharae: 10.1021/NP50085A021
1813065 - Rhamnus pallasii: 10.1007/BF00574350
280022 - Rhamnus prinoides: 10.1002/(SICI)1099-1565(199903/04)10:2<69::AID-PCA447>3.0.CO;2-4
1778787 - Rhamnus punctata: 10.3109/13880209209053982
1819798 - Rhamnus wightii: 10.1016/0031-9422(91)83502-C
3620 - Rheum: 10.1002/(SICI)1099-0801(199807/08)12:4<193::AID-BMC729>3.0.CO;2-7
694412 - Rheum acuminatum: 10.1016/0378-8741(84)90016-3
284362 - Rheum alexandrae: 10.1016/0378-8741(84)90016-3
574896 - Rheum altaicum: 10.1016/0378-8741(84)90016-3
284363 - Rheum australe:
137216 - Rheum compactum: 10.1016/0378-8741(84)90016-3
694413 - Rheum delavayi:
240182 - Rheum franzenbachii:
137217 - Rheum hotaoense: 10.1016/0378-8741(84)90016-3
240183 - Rheum kialense: 10.1016/0378-8741(84)90016-3
137218 - Rheum likiangense: 10.1016/0378-8741(84)90016-3
137219 - Rheum nanum: 10.1055/S-2008-1074562
137697 - Rheum nobile: 10.1016/0378-8741(84)90016-3
137220 - Rheum officinale:
694414 - Rheum palaestinum: 10.1016/S0031-9422(00)00341-1
137221 - Rheum palmatum:
137223 - Rheum pumilum: 10.1016/0378-8741(84)90016-3
2743666 - Rheum racemiferum:
137224 - Rheum reticulatum: 10.1016/0378-8741(84)90016-3
3621 - Rheum rhabarbarum:
46087 - Rheum rhaponticum:
240184 - Rheum spiciforme: 10.1016/0378-8741(84)90016-3
137225 - Rheum sublanceolatum: 10.1055/S-2008-1074562
137226 - Rheum tanguticum:
205071 - Rheum tataricum: 10.1016/0378-8741(84)90016-3
137227 - Rheum undulatum:
137228 - Rheum wittrockii: 10.1016/0378-8741(84)90016-3
267261 - Rosa villosa:
3618 - Rumex: 10.1016/J.BMCL.2013.04.059
273505 - Rumex abyssinicus:
41241 - Rumex acetosa:
1351827 - Rumex alpinus:
1786032 - Rumex chalepensis:
174649 - Rumex crispus:
278676 - Rumex cristatus: 10.1042/BJ0980112
1006352 - Rumex dentatus: 10.1039/P19750000689
174651 - Rumex japonicus:
174652 - Rumex nepalensis:
137229 - Rumex patientia:
1786036 - Rumex pictus: 10.1016/0305-1978(93)90049-W
242528 - Rumex scutatus: 10.1515/ZNC-1997-9-1014
59067 - Ruscus aculeatus: 10.1007/S40278-014-1868-4
268908 - Salvia greggii:
281910 - Sanguisorba alpina: 10.1016/0031-9422(92)80123-V
1353961 - Selaginella delicatula: 10.1007/S10600-011-0013-3
53923 - Senna alata:
72402 - Senna alexandrina:
948713 - Senna auriculata: 10.1111/J.2042-7158.1974.TB09356.X
346959 - Senna corymbosa: 10.1016/0031-9422(92)80483-U
72401 - Senna didymobotrya:
756587 - Senna garrettiana: 10.1111/J.2042-7158.1974.TB09356.X
1842781 - Senna gaudichaudii: 10.1055/S-0028-1097458
346974 - Senna italica:
162908 - Senna lindheimeriana: 10.1016/0031-9422(92)80483-U
2601745 - Senna longiracemosa: 10.1016/S0031-9422(00)95104-5
346975 - Senna macranthera: 10.1111/J.2042-7158.1974.TB09356.X
1288009 - Senna macranthera var. micans:
346985 - Senna obtusifolia:
126820 - Senna occidentalis:
992784 - Senna petersiana: 10.1016/S0367-326X(00)00155-6
346407 - Senna quinquangulata:
346998 - Senna septemtrionalis:
346999 - Senna siamea:
1977557 - Senna singueana:
948718 - Senna sophera:
347003 - Senna spectabilis: 10.1111/J.2042-7158.1974.TB09356.X
948714 - Senna sulfurea: 10.1055/S-0028-1097458
362788 - Senna tora:
347010 - Senna villosa: 10.1016/S0031-9422(00)94783-6
365555 - Shorea worthingtonii: 10.1016/S0031-9422(00)91468-7
66098 - Simethis mattiazzii: 10.3109/13880208509070680
1883 - Streptomyces: 10.1038/JA.2008.63
2382096 - Strossmayeria bakeriana: 10.1016/S0031-9422(00)88708-7
28573 - Talaromyces islandicus: 10.3390/BIOM9020068
5544 - Trichoderma harzianum:
40695 - Trichoderma polysporum: 10.1016/S0031-9422(00)81684-2
5547 - Trichoderma viride: 10.1139/V67-020
263405 - Trirhabda geminata: 10.1515/ZNC-1996-3-417
5691 - Trypanosoma brucei:
1390085 - Ventilago denticulata:
108868 - Ventilago leiocarpa: 10.1021/NP000569D
106720 - Ventilago viminalis: 10.1071/CH9630695
1137045 - Vismia cayennensis: 10.1016/S0031-9422(00)83481-0
999598 - Vismia guianensis:
1348480 - Vismia latifolia: 10.1002/1097-458X(200012)38:12<1027::AID-MRC777>3.0.CO;2-3
29760 - Vitis vinifera: 10.1016/S0278-6915(99)00027-7
72655 - Xanthorrhoea australis: 10.1071/CH9740331

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

Huang-Fei Jin, Qian-Xue Shen, Ying Shi, Fang-Ming Liu, Bin Wang, Jun Cao, Li-Hong Ye. Magnetic-stirring-enhanced mechanical amorphous dispersion extraction for the hydrophobic phytochemical constituents using an aqueous solution from a medicinal plant. Journal of pharmaceutical and biomedical analysis. 2024 Aug; 245(?):116191. doi: 10.1016/j.jpba.2024.116191. [PMID: 38728950]
吉 Deji, Jun Lan, Basangyangzong, Dawazhuoma. [Establishment and Optimization of Quality Standards for the Traditional Tibetan Medicine Preparation of Liuwei Nengxiao Pills]. Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition. 2024 Mar; 55(2):425-432. doi: 10.12182/20240360102. [PMID: 38645843]
Razieh Amini, Shadi Moradi, Rezvan Najafi, Mehrdokht Mazdeh, Amir Taherkhani. BACE1 Inhibition Utilizing Organic Compounds Holds Promise as a Potential Treatment for Alzheimer's and Parkinson's Diseases. Oxidative medicine and cellular longevity. 2024; 2024(?):6654606. doi: 10.1155/2024/6654606. [PMID: 38425997]
Fang Zhang, Rui Wu, Yanfang Liu, Shu Dai, Xinyan Xue, Xiaohong Gong, Yunxia Li. Comparative Pharmacokinetic Study of Rhubarb Anthraquinones in Normal and Nonalcoholic Fatty Liver Disease Rats. European journal of drug metabolism and pharmacokinetics. 2024 Jan; 49(1):111-121. doi: 10.1007/s13318-023-00875-z. [PMID: 38112917]
Huijuan Lv, Jingjing Niu, Wenhao Pan, Yudong Wang, Lifang Wang, Meng Wang, Yali Shi, Guifang Zhang, Bandar Al Hamyari, Shaohua Wang, Xuefeng Li, Yanbin Shi. Stool-softening effect and action mechanism of free anthraquinones extracted from Rheum palmatum L. on water deficit-induced constipation in rats. Journal of ethnopharmacology. 2023 Oct; 319(Pt 3):117336. doi: 10.1016/j.jep.2023.117336. [PMID: 37907143]
H Wang, M Li, S Li, J Shi, L Huang, S Cheng, C Zou, H Yan. [Spectrum-effect relationship of total anthraquinone extract of Cassia seeds against fluorouracil-induced liver injury in mice]. Nan fang yi ke da xue xue bao = Journal of Southern Medical University. 2023 May; 43(5):825-831. doi: 10.12122/j.issn.1673-4254.2023.05.19. [PMID: 37313825]
Hanaa M Sayed, Mahmoud A Ramadan, Heba H Salem, Iqrar Ahmad, Harun Patel, Marwa A A Fayed. Phytochemical Investigation, In silico/In vivo Analgesic, and Anti-inflammatory Assessment of the Egyptian Cassia occidentalis L. Steroids. 2023 May; 196(?):109245. doi: 10.1016/j.steroids.2023.109245. [PMID: 37141980]
Su-Kang Kim, Ju-Yeon Ban, Hyungoo Kang, Sang-Il Park. Anti-Apoptotic Effect of Chrysophanol Isolated from Cassia tora Seed Extract on Blue-Light-Induced A2E-Loaded Human Retinal Pigment Epithelial Cells. International journal of molecular sciences. 2023 Apr; 24(7):. doi: 10.3390/ijms24076676. [PMID: 37047648]
Meng Zhang, Zhi-Xian Ding, Wei Huang, Jing Luo, Shu Ye, Sheng-Lin Hu, Peng Zhou, Biao Cai. Chrysophanol exerts a protective effect against Aβ25-35-induced Alzheimer's disease model through regulating the ROS/TXNIP/NLRP3 pathway. Inflammopharmacology. 2023 Mar; ?(?):. doi: 10.1007/s10787-023-01201-4. [PMID: 36976486]
Dongpeng Wang, Jufeng Duan, Xiao-Jing Chen, Kaiqi Liu, Yingying Guo, Run Shi, Sha Li, Ming Liu, Lijun Zhao, Bei Li, Hongtao Liu, Minglun Li, Yibin Feng, Hongliang Li, Xuanbin Wang. Pharmacokinetic characteristics of emodin in polygoni Multiflori Radix Praeparata. Journal of ethnopharmacology. 2023 Mar; 303(?):115945. doi: 10.1016/j.jep.2022.115945. [PMID: 36435407]
Lingling Wang, Guoying Zhou, Shuo Zhao, Yang Yang. Soluble protein content, bioactive compounds and the antioxidant activity in seeds of ten Rheum tanguticum lines from Qinghai-Tibet Plateau. Chemistry & biodiversity. 2023 Feb; ?(?):e202200901. doi: 10.1002/cbdv.202200901. [PMID: 36788177]
Jiajie Lu, Zhimin Miao, Yuhan Jiang, Weiyi Xia, Xian Wang, Yifeng Shi, Libin Ni, Sunlong Li, Jian Xiao, Sunren Sheng, Haiming Jin. Chrysophanol prevents IL-1β-Induced inflammation and ECM degradation in osteoarthritis via the Sirt6/NF-κB and Nrf2/NF-κB axis. Biochemical pharmacology. 2023 02; 208(?):115402. doi: 10.1016/j.bcp.2022.115402. [PMID: 36592706]
Maria Goretti de Vasconcelos Silva, Daniele Rodrigues de Lima, Jackelyne Alves Monteiro, Francisco Ernani Alves Magalhães. Anxiolytic-like effect of chrysophanol from Senna cana stem in adult zebrafish (Danio rerio). Natural product research. 2022 Sep; 36(17):4426-4430. doi: 10.1080/14786419.2021.1980788. [PMID: 34547943]
Aarti Sharma, Sonalika Bhalla, Sidharth Mehan. PI3K/AKT/mTOR signalling inhibitor chrysophanol ameliorates neurobehavioural and neurochemical defects in propionic acid-induced experimental model of autism in adult rats. Metabolic brain disease. 2022 08; 37(6):1909-1929. doi: 10.1007/s11011-022-01026-0. [PMID: 35687217]
Pengchegn Li, Xiaohan Zhu, Mi Xiao, Yanqi Su, Shanshan Yu, Jintian Tang, Hongkun Xue, Xu Cai. Rapid Isolation and Hypoglycemic Activity of Secondary Metabolites of Eurotium cristatum by High-Speed Countercurrent Chromatography. Journal of chromatographic science. 2022 Mar; ?(?):. doi: 10.1093/chromsci/bmac020. [PMID: 35325046]
Xinquan Li, Yaxun Cheng, Yunpeng Qin, Huawu Gao, Guangyun Wang, Hang Song, Yan Wang, Biao Cai. Chrysophanol exerts neuroprotective effects via interfering with endoplasmic reticulum stress apoptotic pathways in cell and animal models of Alzheimer's disease. The Journal of pharmacy and pharmacology. 2022 Jan; 74(1):32-40. doi: 10.1093/jpp/rgab148. [PMID: 34791341]
Xu Zhao, Dongge Qiao, Dongsheng Guan, Kun Wang, Yinglin Cui. Chrysophanol Ameliorates Hemin-Induced Oxidative Stress and Endoplasmic Reticulum Stress by Regulating MicroRNA-320-5p/Wnt3a Pathway in HT22 Cells. Oxidative medicine and cellular longevity. 2022; 2022(?):9399658. doi: 10.1155/2022/9399658. [PMID: 35936221]
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