alpha-eudesmol (BioDeep_00000007528)

Secondary id: BioDeep_00000227156, BioDeep_00000863391

PANOMIX_OTCML-2023

代谢物信息卡片

2-(4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl)propan-2-ol

化学式: C15H26O (222.1984)
中文名称: α-桉叶醇
谱图信息: 最多检出来源 Viridiplantae(plant) 8.53%

分子结构信息

SMILES: C1C=C([C@@H]2[C@](C1)(CC[C@H](C2)C(C)(C)O)C)C
InChI: InChI=1S/C15H26O/c1-11-6-5-8-15(4)9-7-12(10-13(11)15)14(2,3)16/h6,12-13,16H,5,7-10H2,1-4H3

描述信息

A eudesmane sesquiterpenoid in which the eudesmane skeleton carries a hydroxy substituent at C-11 and has a double bond between C-3 and C-4.

同义名列表

4 个代谢物同义名

alpha-eudesmol; 2-(4a,8-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-2-yl)propan-2-ol; alpha-Eudesmol; alpha-Eudesmol

数据库引用编号

16 个数据库交叉引用编号

ChEBI: CHEBI:10278
ChEBI: CHEBI:157730
KEGG: C09663
PubChem: 92762
PubChem: 521216
Metlin: METLIN67871
ChEMBL: CHEMBL3120654
MetaCyc: CPD-11430
KNApSAcK: C00000163
CAS: 473-16-5
PMhub: MS000020915
MetaboLights: MTBLC10278
PubChem: 11853
3DMET: B03176
NIKKAJI: J12.132K
KNApSAcK: 10278

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)

124 个相关的物种来源信息

78260 - Abies firma: 10.1016/S0031-9422(00)80837-7
97169 - Abies sibirica: 10.1007/BF00600860
299923 - Alpinia flabellata: 10.1002/FFJ.1105
1465234 - Amyris elemifera: 10.1080/10412905.2000.9712037
301862 - Annona reticulata: 10.1016/S0031-9422(98)80072-1
16727 - Aristolochiaceae: 10.1590/S0103-50531999000200009
2707368 - Baccharis aliena: 10.1016/0031-9422(95)00559-5
230209 - Balsamorhiza sagittata: 10.1016/S0031-9422(00)83116-7
198841 - Bupleurum gibraltaricum: 10.1021/NP960732Y
204211 - Callicarpa americana: 10.1021/JF991026G
214225 - Callitris columellaris: 10.1016/S0031-9422(98)00158-7
214224 - Callitris intratropica: 10.1016/S0031-9422(98)00158-7
32201 - Carya illinoinensis: 10.3987/R-1987-02-0447
187461 - Chamaecyparis formosensis:
58030 - Chamaecyparis lawsoniana: 10.1016/0305-1978(85)90081-X
191224 - Cistus creticus: 10.1080/10412905.1994.9698322
2708762 - Cleistopholis patens: 10.1055/S-2006-962450
181186 - Cordia trichotoma: 10.1016/S0031-9422(00)83991-6
87660 - Corymbia maculata: 10.1023/B:JOEC.0000042400.14451.08
87660 - Corymbia maculata: 10.1248/CPB.30.1952
3369 - Cryptomeria japonica:
3369 - Cryptomeria japonica: 10.1111/ICS.12069
79841 - Cymbopogon schoenanthus: 10.1016/J.APJTM.2016.06.009
2807217 - Diplolophium africanum: 10.1163/1574-9347_DNP_E832720
462409 - Dolichorrhiza persica: 10.1016/0031-9422(91)83641-W
2651909 - Eremophila dalyana: 10.1071/CH9870405
1711136 - Eucalyptus amplifolia: 10.1071/CH9661541
1711142 - Eucalyptus angulosa: 10.1002/FFJ.2730090305
1711149 - Eucalyptus approximans: 10.1016/0031-9422(82)85188-1
1711173 - Eucalyptus behriana: 10.1002/FFJ.2730100605
183814 - Eucalyptus brassiana: 10.1080/10412905.1991.9697906
1711189 - Eucalyptus burgessiana: 10.1016/0031-9422(82)85188-1
1711216 - Eucalyptus ceratocorys: 10.1002/FFJ.2730090305
1711242 - Eucalyptus cuprea: 10.1002/FFJ.2730100605
87669 - Eucalyptus delegatensis: 10.1016/S0031-9422(00)84946-8
1711273 - Eucalyptus dolichorhyncha: 10.1002/FFJ.2730090305
1226037 - Eucalyptus fasciculosa: 10.1002/FFJ.2730100605
1711306 - Eucalyptus forrestiana: 10.1002/FFJ.2730090305
582364 - Eucalyptus fraxinoides: 10.1016/0031-9422(82)85188-1
34317 - Eucalyptus globulus: 10.1023/B:JOEC.0000042400.14451.08
34317 - Eucalyptus globulus: 10.1080/10412905.1994.9698428
1711342 - Eucalyptus incrassata: 10.1002/FFJ.2730090305
1226038 - Eucalyptus intertexta: 10.1002/FFJ.2730100605
87673 - Eucalyptus lansdowneana: 10.1002/FFJ.2730100605
34318 - Eucalyptus leucoxylon: 10.1002/FFJ.2730100605
929595 - Eucalyptus macarthurii:
1234623 - Eucalyptus melanophloia: 10.1002/FFJ.2730100605
1711432 - Eucalyptus nova-anglica: 10.1080/10412905.1992.9698006
608815 - Eucalyptus oblonga: 10.1071/CH9630515
1711436 - Eucalyptus ochrophloia: 10.1002/FFJ.2730100605
2660570 - Eucalyptus odorata: 10.1002/FFJ.2730100605
424436 - Eucalyptus paliformis: 10.1016/0031-9422(82)85188-1
183848 - Eucalyptus populnea: 10.1002/FFJ.2730100605
795992 - Eucalyptus porosa: 10.1002/FFJ.2730100605
881203 - Eucalyptus pulverulenta: 10.1055/S-2007-969442
1711536 - Eucalyptus sparsa: 10.1002/FFJ.2730100605
582379 - Eucalyptus stenostoma: 10.1016/0031-9422(82)85188-1
87686 - Eucalyptus stoatei: 10.1002/FFJ.2730090305
1711566 - Eucalyptus tetraptera: 10.1002/FFJ.2730090305
424439 - Eucalyptus triflora: 10.1016/0031-9422(82)85188-1
1711585 - Eucalyptus viridis: 10.1002/FFJ.2730100605
2604028 - Flourensia cernua: 10.1016/S0031-9422(00)86634-0
402569 - Guatteria friesiana:
4397 - Hamamelis virginiana: 10.1055/S-2006-957420
74947 - Hedycarya angustifolia: 10.3987/R-1987-02-0447
489330 - Hexalobus crispiflorus: 10.1016/J.PHYTOCHEM.2003.08.004
3486 - Humulus lupulus: 10.1021/JF00118A056
1202800 - Illicium simonsii: 10.1248/CPB.42.112
211591 - Iphiona scabra:
884033 - Juniperus comitana: 10.1021/NP50040A040
633661 - Juniperus monticola: 10.1021/NP50009A015
2290789 - Juniperus standleyi: 10.1021/NP50040A040
884047 - Juniperus taxifolia: 10.1016/0305-1978(85)90081-X
313966 - Laggera: 10.1016/S0031-9422(98)80077-0
85223 - Laurus nobilis: 10.1016/S0024-3205(00)00542-7
268881 - Lepechinia chamaedryoides: 10.1055/S-2006-961452
1671999 - Leplaea cedrata: 10.1080/10412905.1995.9698502
295139 - Leptospermum scoparium: 10.1016/J.PHYTOCHEM.2004.03.019
289720 - Lithraea molleoides: 10.1021/JF00116A075
349509 - Magnolia obovata: 10.1248/CPB.49.716
190902 - Mentha aquatica: 10.1271/NOGEIKAGAKU1924.67.1417
489341 - Monocyclanthus vignei: 10.1016/0031-9422(92)80456-O
199268 - Olearia phlogopappa: 10.1080/10412905.1993.9698243
39352 - Origanum vulgare: 10.1055/S-2006-957640
178131 - Osbornia octodonta: 10.1080/10412905.1993.9698162
196012 - Pegolettia oxyodonta: 10.1016/S0031-9422(00)97892-0
253082 - Pelargonium quercifolium: 10.1080/10412905.1991.9697953
487997 - Persicaria hydropiperoides: 10.3390/MOLECULES191119220
488003 - Persicaria minor: 10.3390/MOLECULES191119220
1155347 - Persicaria mitis: 10.3390/MOLECULES191119220
460663 - Porella perrottetiana: 10.1016/S0031-9422(99)00299-X
1225816 - Psiadia altissima: 10.1080/10412905.1994.9699347
120290 - Psidium guajava: 10.1002/FFJ.2730060314
2602891 - Psidium salutare: 10.1021/JF0116303
1071199 - Pterocarpus santalinus: 10.1016/S0031-9422(00)91365-7
1044948 - Rhododendron calostrotum: 10.1016/S0031-9422(00)81225-X
2291153 - Rhododendron concinnum: 10.1016/S0031-9422(00)81225-X
1701186 - Rhododendron cuneatum: 10.1016/S0031-9422(00)81225-X
2946426 - Rhododendron dasypetalum: 10.1016/S0031-9422(00)81225-X
880079 - Rhododendron dauricum: 10.1016/S0031-9422(00)81225-X
49162 - Rhododendron edgeworthii: 10.1016/S0031-9422(00)81225-X
2946434 - Rhododendron glaucophyllum: 10.1016/S0031-9422(00)81225-X
4347 - Rhododendron hippophaeoides: 10.1016/S0031-9422(00)81225-X
308417 - Rhododendron impeditum: 10.1016/S0031-9422(00)81225-X
1701203 - Rhododendron intricatum: 10.1016/S0031-9422(00)81225-X
118362 - Rhododendron keiskei: 10.1016/S0031-9422(00)81225-X
1044962 - Rhododendron lepidotum: 10.1016/S0031-9422(00)81225-X
313331 - Rhododendron lutescens: 10.1016/S0031-9422(00)81225-X
118363 - Rhododendron micranthum: 10.1016/S0031-9422(00)81225-X
313337 - Rhododendron moupinense: 10.1016/S0031-9422(00)81225-X
105903 - Rhododendron mucronulatum: 10.1007/BF01386197
2878222 - Rhododendron polycladum: 10.1016/S0031-9422(00)81225-X
1701232 - Rhododendron rupicola var. chryseum: 10.1016/S0031-9422(00)81225-X
191006 - Rhododendron virgatum: 10.1016/S0031-9422(00)81225-X
1701247 - Rhododendron xanthocodon: 10.1016/S0031-9422(00)81225-X
1933698 - Salvia absconditiflora: 10.1080/10412905.1995.9698479
1933710 - Salvia caespitosa: 10.1080/10412905.1995.9698508
933125 - Salvia cinnabarina: 10.1002/(SICI)1099-1573(1998)12:1+3.0.CO;2-2
38869 - Salvia sclarea:
43851 - Schinus molle: 10.1021/JF00116A075
4111 - Solanum melongena: 10.1139/V86-001
3317 - Thuja occidentalis:
89194 - Thuja standishii: 10.1016/0305-1978(85)90081-X
2878271 - Thymus camphoratus: 10.1016/S0031-9422(97)00117-9

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	11	CASP3, CNR1, ELANE, ESR1, FPR1, FPR2, NOS2, PGR, PPARG, PTGS2, TYR
Peripheral membrane protein	3	CYP27A1, ESR1, PTGS2
Endoplasmic reticulum membrane	1	PTGS2
Mitochondrion membrane	1	CYP27A1
Nucleus	8	CASP3, ESR1, JUND, NCOA1, NOS2, PGR, PPARA, PPARG
cytosol	8	CASP3, ELANE, ESR1, LIPE, NCOA1, NOS2, PGR, PPARG
phagocytic vesicle	1	ELANE
nucleoplasm	8	CASP3, ESR1, JUND, NCOA1, NOS2, PGR, PPARA, PPARG
RNA polymerase II transcription regulator complex	3	JUND, NCOA1, PPARG
Cell membrane	6	CNR1, ESR1, FPR1, FPR2, LIPE, TNF
Cytoplasmic side	1	ESR1
Cell projection, axon	1	CNR1
Multi-pass membrane protein	3	CNR1, FPR1, FPR2
Synapse	1	TAC1
cell surface	2	ELANE, TNF
glutamatergic synapse	2	CASP3, CNR1
Golgi apparatus	1	ESR1
growth cone	1	CNR1
mitochondrial inner membrane	1	CYP27A1
neuronal cell body	3	CASP3, TAC1, TNF
presynaptic membrane	1	CNR1
Cytoplasm, cytosol	2	LIPE, NOS2
Lysosome	1	TYR
Presynapse	1	CNR1
plasma membrane	8	CNR1, ESR1, FPR1, FPR2, NCOA1, NOS2, PGR, TNF
Membrane	4	ESR1, FPR1, FPR2, LIPE
axon	2	CNR1, TAC1
caveola	2	LIPE, PTGS2
extracellular exosome	1	ELANE
endoplasmic reticulum	1	PTGS2
extracellular space	4	ELANE, IL17A, TAC1, TNF
perinuclear region of cytoplasm	3	NOS2, PPARG, TYR
mitochondrion	1	CYP27A1
protein-containing complex	3	ESR1, NCOA1, PTGS2
intracellular membrane-bounded organelle	2	PPARG, TYR
Microsome membrane	1	PTGS2
postsynaptic density	1	CASP3
Single-pass type I membrane protein	1	TYR
Secreted	1	IL17A
extracellular region	4	ELANE, IL17A, TAC1, TNF
Mitochondrion outer membrane	1	CNR1
mitochondrial outer membrane	2	CNR1, PGR
mitochondrial matrix	1	CYP27A1
transcription regulator complex	3	ESR1, JUND, NCOA1
external side of plasma membrane	2	IL17A, TNF
actin cytoskeleton	1	CNR1
Melanosome membrane	1	TYR
Cytoplasm, P-body	1	NOS2
P-body	1	NOS2
Golgi-associated vesicle	1	TYR
recycling endosome	1	TNF
Single-pass type II membrane protein	1	TNF
Cytoplasm, perinuclear region	1	NOS2
Mitochondrion inner membrane	1	CYP27A1
Membrane raft	2	CNR1, TNF
GABA-ergic synapse	1	CNR1
Peroxisome	1	NOS2
peroxisomal matrix	1	NOS2
collagen-containing extracellular matrix	1	ELANE
secretory granule	1	ELANE
Nucleus inner membrane	1	PTGS2
Nucleus outer membrane	1	PTGS2
nuclear inner membrane	1	PTGS2
nuclear outer membrane	1	PTGS2
receptor complex	1	PPARG
neuron projection	1	PTGS2
chromatin	6	ESR1, JUND, NCOA1, PGR, PPARA, PPARG
phagocytic cup	1	TNF
Lipid droplet	1	LIPE
Membrane, caveola	1	LIPE
specific granule membrane	1	FPR2
tertiary granule membrane	1	FPR2
Melanosome	1	TYR
euchromatin	1	ESR1
secretory granule membrane	1	FPR1
endoplasmic reticulum lumen	1	PTGS2
transcription repressor complex	2	ELANE, JUND
specific granule lumen	1	ELANE
azurophil granule membrane	1	FPR1
azurophil granule lumen	1	ELANE
[Isoform 1]: Nucleus	1	ESR1
ficolin-1-rich granule membrane	2	FPR1, FPR2
death-inducing signaling complex	1	CASP3
Cytoplasmic vesicle, phagosome	1	ELANE
transcription factor AP-1 complex	1	JUND
[Tumor necrosis factor, soluble form]: Secreted	1	TNF
cortical cytoskeleton	1	NOS2
[Isoform 4]: Mitochondrion outer membrane	1	PGR
[C-domain 2]: Secreted	1	TNF
[Tumor necrosis factor, membrane form]: Membrane	1	TNF
[C-domain 1]: Secreted	1	TNF

文献列表

Emmanoel V Costa, Leociley R Alencar Menezes, Lívia M Dutra, Maria Lúcia B Pinheiro, Érica M Lavor, Mariana G Silva, Cristiane Dos S C Alves, Jackson R G S Almeida, Felipe Moura A da Silva, Hector H F Koolen, Andersson Barison. A novel eudesmol derivative from the leaf essential oil of Guatteria friesiana (Annonaceae) and evaluation of the antinociceptive activity. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2022 May; ?(?):. doi: 10.1515/znc-2022-0059. [PMID: 35579663]
Yoshinori Asakawa, Agnieszka Ludwiczuk. Chemical Constituents of Bryophytes: Structures and Biological Activity. Journal of natural products. 2018 03; 81(3):641-660. doi: 10.1021/acs.jnatprod.6b01046. [PMID: 29019405]
Fatma Zohra Rahali, Myriam Lamine, Mahmoud Gargouri, Iness Bettaieb Rebey, Majdi Hammami, Ibtissem Hamrouni Sellami. Metabolite profiles of essential oils and molecular markers analysis to explore the biodiversity of Ferula communis: Towards conservation of the endemic giant fennel. Phytochemistry. 2016 Apr; 124(?):58-67. doi: 10.1016/j.phytochem.2016.01.012. [PMID: 26826740]
Danielle Cardoso de Alencar, Maria Lúcia Belém Pinheiro, José Lamak da Silva Pereira, João Ernesto de Carvalho, Francinete Ramos Campos, Alessandra Freitas Serain, Ricardo Brunelli Tirico, Alvaro José Hernández-Tasco, Emmanoel Vilaça Costa, Marcos José Salvador. Chemical composition of the essential oil from the leaves of Anaxagorea brevipes (Annonaceae) and evaluation of its bioactivity. Natural product research. 2016; 30(9):1088-92. doi: 10.1080/14786419.2015.1101103. [PMID: 26586465]
Filippo Maggi, Fabrizio Papa, Stefano Dall'Acqua, Marcello Nicoletti. Chemical analysis of essential oils from different parts of Ferula communis L. growing in central Italy. Natural product research. 2016; 30(7):806-13. doi: 10.1080/14786419.2015.1071365. [PMID: 26299522]
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Dharmendra K Yadav, Vipin Mudgal, Jyoti Agrawal, Anil K Maurya, Dnyaneshwar U Bawankule, Chandan S Chanotiya, Feroz Khan, Sanjog T Thul. Molecular docking and ADME studies of natural compounds of Agarwood oil for topical anti-inflammatory activity. Current computer-aided drug design. 2013 Sep; 9(3):360-70. doi: 10.2174/1573409911309030012. [PMID: 23566359]
Anny C S Britto, Allan C A de Oliveira, Raissa M Henriques, Gabriella M B Cardoso, Diogo S Bomfim, Adriana A Carvalho, Manoel O Moraes, Claudia Pessoa, Maria L B Pinheiro, Emmanoel V Costa, Daniel P Bezerra. In vitro and in vivo antitumor effects of the essential oil from the leaves of Guatteria friesiana. Planta medica. 2012 Mar; 78(5):409-14. doi: 10.1055/s-0031-1298173. [PMID: 22274812]
Mehdi Mohammadi, Maryam Yousefi, Zohreh Habibi, Dara Dastan. Chemical composition and antioxidant activity of the essential oil of aerial parts of Petasites albus from Iran: a good natural source of euparin. Natural product research. 2012; 26(4):291-7. doi: 10.1080/14786410903374819. [PMID: 21416453]
L Y Mou, L Y Zhu, Z Y Lin, X T Liang. Stereoselective total synthesis of chrysanthemol. Journal of Asian natural products research. 2001; 3(2):103-16. doi: 10.1080/10286020108041377. [PMID: 11407809]
K Asakura, T Kanemasa, K Minagawa, K Kagawa, T Yagami, M Nakajima, M Ninomiya. alpha-eudesmol, a P/Q-type Ca(2+) channel blocker, inhibits neurogenic vasodilation and extravasation following electrical stimulation of trigeminal ganglion. Brain research. 2000 Aug; 873(1):94-101. doi: 10.1016/s0006-8993(00)02527-0. [PMID: 10915814]
K Asakura, T Kanemasa, K Minagawa, K Kagawa, M Ninomiya. The nonpeptide alpha-eudexp6l from Juniperus virginiana Linn. (Cupressaceae) inhibits omega-agatoxin IVA-sensitive Ca2+ currents and synaptosomal 45Ca2+ uptake. Brain research. 1999 Mar; 823(1-2):169-76. doi: 10.1016/s0006-8993(99)01165-8. [PMID: 10095023]
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