totarol (BioDeep_00000403588)
natural product
代谢物信息卡片
化学式: C20H30O (286.229653)
中文名称: (4bS)-反式-8,8-三甲基-4b,5,6,7,8,8a,9,10-八氢-1-异丙基菲蒽-2-醇
谱图信息:
最多检出来源 Homo sapiens(natural_products) 50%
分子结构信息
SMILES: CC(C)C1=C(C=CC2=C1CCC3C2(CCCC3(C)C)C)O
InChI: InChI=1S/C20H30O/c1-13(2)18-14-7-10-17-19(3,4)11-6-12-20(17,5)15(14)8-9-16(18)21/h8-9,13,17,21H,6-7,10-12H2,1-5H3/t17-,20+/m0/s1
描述信息
A natural product found in Biota orientalis.
同义名列表
10 个代谢物同义名
totarol; 4bS-trans-8,8-Trimethyl-4b,5,6,7,8,8a,9,10-octahydro-1-isopropyl-phenanthren-2-ol; (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol; 4b,5,6,7,8,8a,9,10-Octahydro-4b,8,8-trimethyl-1-(1-methylethyl)-2-phenanthrenol; (4bS,8aS)-1-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol; 14-Isopropylpodocarpa-8,11,13-trien-13-ol; BCBcMAP01_000081; 532657_ALDRICH; SMP1_000215; NCGC00385162-01_C20H30O_14-Isopropylpodocarpa-8,11,13-trien-13-ol
数据库引用编号
15 个数据库交叉引用编号
- ChEBI: CHEBI:69241
- PubChem: 92783
- Metlin: METLIN43695
- ChEMBL: CHEMBL487602
- CAS: 511-15-9
- MoNA: MoNA041629
- MoNA: VF-NPL-LTQ006046
- MoNA: VF-NPL-LTQ006045
- MoNA: VF-NPL-QEHF002658
- MoNA: VF-NPL-QEHF002657
- MoNA: VF-NPL-QEHF002656
- MoNA: CCMSLIB00000851410
- MetaboLights: MTBLC69241
- LOTUS: LTS0175490
- LOTUS: LTS0097200
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)
157 个相关的物种来源信息
- 120582 - Afrocarpus: LTS0097200
- 120582 - Afrocarpus: LTS0175490
- 56897 - Afrocarpus falcatus: 10.1016/S0031-9422(00)80328-3
- 56897 - Afrocarpus falcatus: LTS0097200
- 165205 - Afrocarpus gracilior: 10.1016/S0031-9422(00)80328-3
- 165205 - Afrocarpus gracilior: LTS0097200
- 165205 - Afrocarpus gracilior: LTS0175490
- 7458 - Apidae: LTS0097200
- 7459 - Apis: LTS0097200
- 7460 - Apis mellifera: 10.1016/J.PHYTOCHEM.2009.07.025
- 7460 - Apis mellifera: 10.3390/IJMS15022327
- 7460 - Apis mellifera: LTS0097200
- 6656 - Arthropoda: LTS0097200
- 329095 - Callitropsis: LTS0097200
- 329095 - Callitropsis: LTS0175490
- 85954 - Callitropsis nootkatensis: 10.1016/S0367-326X(01)00272-6
- 85954 - Callitropsis nootkatensis: LTS0097200
- 85954 - Callitropsis nootkatensis: LTS0175490
- 13414 - Chamaecyparis: LTS0097200
- 13414 - Chamaecyparis: LTS0175490
- 187461 - Chamaecyparis formosensis: 10.1016/S0031-9422(99)00074-6
- 187461 - Chamaecyparis formosensis: LTS0097200
- 187461 - Chamaecyparis formosensis: LTS0175490
- 13415 - Chamaecyparis obtusa: 10.1271/BBB1961.48.2523
- 13415 - Chamaecyparis obtusa: LTS0097200
- 99808 - Chamaecyparis pisifera: 10.1271/BBB1961.48.2523
- 99808 - Chamaecyparis pisifera: LTS0097200
- 1097172 - Conchidium: LTS0097200
- 1097172 - Conchidium: LTS0175490
- 3368 - Cryptomeria: LTS0097200
- 3368 - Cryptomeria: LTS0175490
- 3369 - Cryptomeria japonica: 10.1016/S0031-9422(00)89538-2
- 3369 - Cryptomeria japonica: 10.1016/S0031-9422(00)94837-4
- 3369 - Cryptomeria japonica: LTS0097200
- 3369 - Cryptomeria japonica: LTS0175490
- 3367 - Cupressaceae: LTS0097200
- 3367 - Cupressaceae: LTS0175490
- 13468 - Cupressus: LTS0097200
- 13468 - Cupressus: LTS0175490
- 13469 - Cupressus sempervirens: 10.1016/S0040-4039(00)90571-9
- 13469 - Cupressus sempervirens: LTS0097200
- 50180 - Dacrycarpus: LTS0097200
- 120585 - Dacrycarpus vieillardii: 10.1016/S0031-9422(00)80328-3
- 120585 - Dacrycarpus vieillardii: LTS0097200
- 2759 - Eukaryota: LTS0097200
- 2759 - Eukaryota: LTS0175490
- 50557 - Insecta: LTS0097200
- 186771 - Jungermanniopsida: LTS0097200
- 13100 - Juniperus: LTS0097200
- 13100 - Juniperus: LTS0175490
- 50182 - Juniperus chinensis: 10.1016/0031-9422(93)85043-Q
- 50182 - Juniperus chinensis: 10.1016/0031-9422(95)00795-4
- 50182 - Juniperus chinensis: 10.1016/S0031-9422(00)90849-5
- 50182 - Juniperus chinensis: 10.1248/CPB.42.1774
- 50182 - Juniperus chinensis: LTS0097200
- 50182 - Juniperus chinensis: LTS0175490
- 58039 - Juniperus communis: 10.1016/J.JEP.2009.09.007
- 58039 - Juniperus communis: LTS0097200
- 453927 - Juniperus formosana: 10.1248/CPB.38.3195
- 453927 - Juniperus formosana: LTS0097200
- 61308 - Juniperus phoenicea: 10.1080/14786419.2010.523827
- 61308 - Juniperus phoenicea: LTS0097200
- 99809 - Juniperus rigida: LTS0097200
- 99809 - Juniperus rigida: LTS0175490
- 13102 - Juniperus rigida var. conferta: 10.1016/S0031-9422(00)88478-2
- 13102 - Juniperus rigida var. conferta: LTS0097200
- 13102 - Juniperus rigida var. conferta: LTS0175490
- 4447 - Liliopsida: LTS0097200
- 4447 - Liliopsida: LTS0175490
- 3398 - Magnoliopsida: LTS0097200
- 3398 - Magnoliopsida: LTS0175490
- 3195 - Marchantiophyta: LTS0097200
- 33208 - Metazoa: LTS0097200
- 36011 - Nageia: LTS0097200
- 36011 - Nageia: LTS0175490
- 36012 - Nageia nagi: 10.1007/BF01969731
- 36012 - Nageia nagi: 10.1016/0031-9422(91)85049-6
- 36012 - Nageia nagi: 10.1021/NP50088A008
- 36012 - Nageia nagi: 10.1055/S-2006-957655
- 36012 - Nageia nagi: LTS0097200
- 36012 - Nageia nagi: LTS0175490
- 147280 - Nageia wallichiana: 10.1021/NP50033A041
- 147280 - Nageia wallichiana: LTS0097200
- 4747 - Orchidaceae: LTS0097200
- 4747 - Orchidaceae: LTS0175490
- 58019 - Pinopsida: LTS0097200
- 58019 - Pinopsida: LTS0175490
- 13637 - Platycladus: LTS0097200
- 13637 - Platycladus: LTS0175490
- 58046 - Platycladus orientalis: 10.1021/NP200317P
- 58046 - Platycladus orientalis: 10.1055/S-2006-957995
- 58046 - Platycladus orientalis: 10.1271/BBB1961.48.2523
- 58046 - Platycladus orientalis: LTS0097200
- 58046 - Platycladus orientalis: LTS0175490
- 3362 - Podocarpaceae: LTS0097200
- 3362 - Podocarpaceae: LTS0175490
- 3363 - Podocarpus: LTS0097200
- 3363 - Podocarpus: LTS0175490
- 1030187 - Podocarpus affinis: 10.1016/S0031-9422(00)80328-3
- 1030187 - Podocarpus affinis: LTS0097200
- 1030187 - Podocarpus affinis: LTS0175490
- 61307 - Podocarpus neriifolius: 10.1016/S0031-9422(00)80328-3
- 61307 - Podocarpus neriifolius: LTS0097200
- 61307 - Podocarpus neriifolius: LTS0175490
- 1030204 - Podocarpus rumphii: 10.1016/S0031-9422(00)80328-3
- 1030204 - Podocarpus rumphii: LTS0097200
- 455468 - Podocarpus sylvestris: 10.1016/S0031-9422(00)80328-3
- 455468 - Podocarpus sylvestris: LTS0097200
- 455468 - Podocarpus sylvestris: LTS0175490
- 56901 - Podocarpus totara: 10.1071/CH9710217
- 56901 - Podocarpus totara: LTS0097200
- 56901 - Podocarpus totara: LTS0175490
- 58044 - Retrophyllum: LTS0097200
- 58044 - Retrophyllum: LTS0175490
- 120638 - Retrophyllum comptonii: 10.1016/S0031-9422(00)80328-3
- 120638 - Retrophyllum comptonii: 10.1021/NP50033A041
- 120638 - Retrophyllum comptonii: LTS0097200
- 120638 - Retrophyllum comptonii: LTS0175490
- 58045 - Retrophyllum minus: 10.1071/CH9710217
- 58045 - Retrophyllum minus: LTS0097200
- 58045 - Retrophyllum minus: LTS0175490
- 95791 - Schistochila: LTS0097200
- 399161 - Schistochila acuminata: 10.1080/10286020108041397
- 399161 - Schistochila acuminata: LTS0097200
- 95774 - Schistochilaceae: LTS0097200
- 35493 - Streptophyta: LTS0097200
- 35493 - Streptophyta: LTS0175490
- 13716 - Tetraclinis: LTS0097200
- 13716 - Tetraclinis: LTS0175490
- 13717 - Tetraclinis articulata: 10.1021/NP0204949
- 13717 - Tetraclinis articulata: 10.3891/ACTA.CHEM.SCAND.16-1291
- 13717 - Tetraclinis articulata: LTS0097200
- 13717 - Tetraclinis articulata: LTS0175490
- 3315 - Thuja: LTS0097200
- 3315 - Thuja: LTS0175490
- 3317 - Thuja occidentalis: 10.1080/10412905.1993.9698189
- 3317 - Thuja occidentalis: LTS0097200
- 3316 - Thuja plicata: 10.1016/S0305-1978(00)00047-8
- 3316 - Thuja plicata: LTS0097200
- 89194 - Thuja standishii: 10.1016/S0968-0896(01)00099-2
- 89194 - Thuja standishii: 10.1055/S-2002-33787
- 89194 - Thuja standishii: 10.1246/NIKKASHI1948.91.7_664
- 89194 - Thuja standishii: LTS0097200
- 89194 - Thuja standishii: LTS0175490
- 13726 - Thujopsis: LTS0097200
- 13726 - Thujopsis: LTS0175490
- 13727 - Thujopsis dolabrata: 10.1016/0031-9422(82)83156-7
- 13727 - Thujopsis dolabrata: 10.1271/BBB1961.48.2523
- 13727 - Thujopsis dolabrata: LTS0097200
- 13727 - Thujopsis dolabrata: LTS0175490
- 58023 - Tracheophyta: LTS0097200
- 58023 - Tracheophyta: LTS0175490
- 33090 - Viridiplantae: LTS0097200
- 33090 - Viridiplantae: LTS0175490
- 257622 - Xanthocyparis: LTS0097200
- 257622 - Xanthocyparis: LTS0175490
- 33090 - 紫草: -
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
- Samia Belahcene, Widad Kebsa, Tomilola Victor Akingbade, Haruna Isiyaku Umar, Damilola Alex Omoboyowa, Abdulaziz A Alshihri, Adel Abo Mansour, Abdulaziz Hassan Alhasaniah, Mohammed A Oraig, Youssef Bakkour, Essaid Leghouchi. Chemical Composition Antioxidant and Anti-Inflammatory Activities of Myrtus communis L. Leaf Extract: Forecasting ADMET Profiling and Anti-Inflammatory Targets Using Molecular Docking Tools.
Molecules (Basel, Switzerland).
2024 Feb; 29(4):. doi:
10.3390/molecules29040849
. [PMID: 38398601] - Yasemin Yücel Yücel, Hüseyin Servi, Kaan Polatoğlu, Ayşe Nalbantsoy. Anthemis tricolor Containing Unusual Totarol with Cytotoxic and Acetylcholinesterase-Inhibitory Activity.
Chemistry & biodiversity.
2024 Feb; 21(2):e202300913. doi:
10.1002/cbdv.202300913
. [PMID: 38116908] - Tong Xu, Lunhua Huang, Zhiqiang Liu, Dongwen Ma, Guowei Zhang, Xiaofei Ning, Xinyang Lu, Hongsheng Liu, Biao Jiang. Totarol, a natural diterpenoid, induces selective antitumor activity in SGC-7901 human gastric carcinoma cells by triggering apoptosis, cell cycle disruption and suppression of cancer cell migration.
Journal of B.U.ON. : official journal of the Balkan Union of Oncology.
2019 Mar; 24(2):686-692. doi:
. [PMID: 31128024]
- Ce Shi, Xingchen Zhao, Wenli Li, Rizeng Meng, Zonghui Liu, Mingyuan Liu, Na Guo, Lu Yu. Inhibitory effect of totarol on exotoxin proteins hemolysin and enterotoxins secreted by Staphylococcus aureus.
World journal of microbiology & biotechnology.
2015 Oct; 31(10):1565-73. doi:
10.1007/s11274-015-1905-3
. [PMID: 26193949] - Chen-Lung Ho, Kuo-Feng Hua, Kuan-Ping Hsu, Eugene I-chen Wang, Yu-Chang Su. Composition and antipathogenic activities of the twig essential oil of Chamaecyparis formosensis from Taiwan.
Natural product communications.
2012 Jul; 7(7):933-6. doi:
"
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Nature communications.
2012 Feb; 3(?):680. doi:
10.1038/ncomms1680
. [PMID: 22353711] - Mark B Yunker, Cara L Lachmuth, Walter J Cretney, Brian R Fowler, Neil Dangerfield, Linda White, Peter S Ross. Biota: sediment partitioning of aluminium smelter related PAHs and pulp mill related diterpenes by intertidal clams at Kitimat, British Columbia.
Marine environmental research.
2011 Sep; 72(3):105-26. doi:
10.1016/j.marenvres.2011.06.004
. [PMID: 21788067] - Andréa Y Gordien, Alexander I Gray, Scott G Franzblau, Véronique Seidel. Antimycobacterial terpenoids from Juniperus communis L. (Cuppressaceae).
Journal of ethnopharmacology.
2009 Dec; 126(3):500-5. doi:
10.1016/j.jep.2009.09.007
. [PMID: 19755141] - Volodymyr Samoylenko, D Chuck Dunbar, Md Abdul Gafur, Shabana I Khan, Samir A Ross, Jaber S Mossa, Farouk S El-Feraly, Babu L Tekwani, Jan Bosselaers, Ilias Muhammad. Antiparasitic, nematicidal and antifouling constituents from Juniperus berries.
Phytotherapy research : PTR.
2008 Dec; 22(12):1570-6. doi:
10.1002/ptr.2460
. [PMID: 19067375] - Kimihiko Sato, Keito Sugawara, Hirono Takeuchi, Hyun-Sun Park, Toshiyuki Akiyama, Tetsuo Koyama, Yutaka Aoyagi, Koichi Takeya, Takanori Tsugane, Susumu Shimura. Antibacterial novel phenolic diterpenes from Podocarpus macrophyllus D. Don.
Chemical & pharmaceutical bulletin.
2008 Dec; 56(12):1691-7. doi:
10.1248/cpb.56.1691
. [PMID: 19043241] - Mi Kyeong Lee, Hyekyung Yang, Jeong Seon Yoon, Eun Ju Jeong, Do Yoon Kim, Na Ry Ha, Sang Hyun Sung, Young Choong Kim. Antifibrotic activity of diterpenes from Biota orientalis leaves on hepatic stellate cells.
Archives of pharmacal research.
2008 Jul; 31(7):866-71. doi:
10.1007/s12272-001-1239-9
. [PMID: 18704328] - Keiko Yamaji, Shigeta Mori, Masaru Akiyama, Atsushi Kato, Tadakazu Nakashima. The antifungal compound totarol of Thujopsis dolabrata var. hondai seeds selects for fungi on seedling root surfaces.
Journal of chemical ecology.
2007 Dec; 33(12):2254-65. doi:
10.1007/s10886-007-9390-2
. [PMID: 18026796] - Jaber S Mossa, Farouk S El-Feraly, Ilias Muhammad. Antimycobacterial constituents from Juniperus procera, Ferula communis and Plumbago zeylanica and their in vitro synergistic activity with isonicotinic acid hydrazide.
Phytotherapy research : PTR.
2004 Nov; 18(11):934-7. doi:
10.1002/ptr.1420
. [PMID: 15597311] - Cailean Clarkson, Chitalu C Musonda, Kelly Chibale, William E Campbell, Peter Smith. Synthesis of totarol amino alcohol derivatives and their antiplasmodial activity and cytotoxicity.
Bioorganic & medicinal chemistry.
2003 Oct; 11(20):4417-22. doi:
10.1016/s0968-0896(03)00491-7
. [PMID: 13129578] - Angela Bernabeu, S Shapiro, José Villalaín. A MAS-NMR study of the location of (+)-totarol, a diterpenoid bioactive molecule, in phospholipid model membranes.
Chemistry and physics of lipids.
2002 Oct; 119(1-2):33-9. doi:
10.1016/s0009-3084(02)00050-6
. [PMID: 12270671] - Toshifumi Minami, Manabu Iwamoto, Hironori Ohtsu, Hirofumi Ohishi, Reiko Tanaka, Akira Yoshitake. Aromatase inhibitory activities of standishinal and the diterpenoids from the bark of Thuja standishii.
Planta medica.
2002 Aug; 68(8):742-5. doi:
10.1055/s-2002-33787
. [PMID: 12221600] - M Iwamoto, H Ohtsu, H Tokuda, H Nishino, S Matsunaga, R Tanaka. Anti-tumor promoting diterpenes from the stem bark of Thuja standishii (Cupressaceae).
Bioorganic & medicinal chemistry.
2001 Jul; 9(7):1911-21. doi:
10.1016/s0968-0896(01)00099-2
. [PMID: 11425594] - G H Constantine, J J Karchesy, S G Franzblau, L E LaFleur. (+)-Totarol from Chamaecyparis nootkatensis and activity against Mycobacterium tuberculosis.
Fitoterapia.
2001 Jun; 72(5):572-4. doi:
10.1016/s0367-326x(01)00272-6
. [PMID: 11429259] - V Micol, C R Mateo, S Shapiro, F J Aranda, J Villalaín. Effects of (+)-totarol, a diterpenoid antibacterial agent, on phospholipid model membranes.
Biochimica et biophysica acta.
2001 Apr; 1511(2):281-90. doi:
10.1016/s0005-2736(01)00284-x
. [PMID: 11286971] - C R Mateo, M Prieto, V Micol, S Shapiro, J Villalaín. A fluorescence study of the interaction and location of (+)-totarol, a diterpenoid bioactive molecule, in model membranes.
Biochimica et biophysica acta.
2000 Dec; 1509(1-2):167-75. doi:
10.1016/s0005-2736(00)00291-1
. [PMID: 11118528] - G B Evans, R H Furneaux. The synthesis and antibacterial activity of totarol derivatives. Part 2: Modifications at C-12 and O-13.
Bioorganic & medicinal chemistry.
2000 Jul; 8(7):1653-62. doi:
10.1016/s0968-0896(00)00095-x
. [PMID: 10976513] - G B Evans, R H Furneaux, G J Gainsford, M P Murphy. The synthesis and antibacterial activity of totarol derivatives. Part 3: Modification of ring-B.
Bioorganic & medicinal chemistry.
2000 Jul; 8(7):1663-75. doi:
10.1016/s0968-0896(00)00096-1
. [PMID: 10976514] - H Haraguchi, H Ishikawa, I Kubo. Antioxidative action of diterpenoids from Podocarpus nagi.
Planta medica.
1997 Jun; 63(3):213-5. doi:
10.1055/s-2006-957655
. [PMID: 9225601] - H Haraguchi, H Ishikawa, S Sakai, B P Ying, I Kubo. Inhibition of lipid peroxidation by diterpenoid from Podocarpus nagi.
Experientia.
1996 Jun; 52(6):573-6. doi:
10.1007/bf01969731
. [PMID: 8698092] - H Haraguchi, S Oike, H Muroi, I Kubo. Mode of antibacterial action of totarol, a diterpene from Podocarpus nagi.
Planta medica.
1996 Apr; 62(2):122-5. doi:
10.1055/s-2006-957832
. [PMID: 8657742] - I Kubo, H Muroi, M Himejima. Antibacterial activity of totarol and its potentiation.
Journal of natural products.
1992 Oct; 55(10):1436-40. doi:
10.1021/np50088a008
. [PMID: 1453180]