Jervine (BioDeep_00000230186)

Main id: BioDeep_00000002009

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(2R,3S,3R,3aS,6S,6aS,6bS,7aR,11aS,1 1bR)-2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11a,11b-hexad ecahydro-3-hydroxy-3,6,10,11b-tetramethyl-Spiro[9H -benzo[a]fluorene-9,2(3H)-furo[3,2-b]pyridin]-11(1 H)-one

化学式: C27H39NO3 (425.293)
中文名称: 蒜黎芦碱, 介芬胺, 蒜藜芦碱
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CC1=C2C(=O)C3C(CC=C4CC(O)CCC43C)C2CCC12OC1CC(C)CNC1C2C
InChI: InChI=1S/C27H39NO3/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-/m0/s1

描述信息

Jervine is a member of piperidines.
Jervine is a natural product found in Veratrum stamineum, Veratrum grandiflorum, and other organisms with data available.
Jervine is a steroidal alkaloid with molecular formula C27H39NO3 which is derived from the Veratrum plant genus. Similar to cyclopamine, which also occurs in the Veratrum genus, it is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation.
D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents > D014704 - Veratrum Alkaloids
Jervine (11-Ketocyclopamine) is a potent Hedgehog (Hh) inhibitor with an IC50 of 500-700 nM[1]. Jervine is a natural teratogenic sterodial alkaloid from rhizomes of Veratrum nigrum. Jervine has anti-inflammatory and antioxidant properties[2].
Jervine (11-Ketocyclopamine) is a potent Hedgehog (Hh) inhibitor with an IC50 of 500-700 nM[1]. Jervine is a natural teratogenic sterodial alkaloid from rhizomes of Veratrum nigrum. Jervine has anti-inflammatory and antioxidant properties[2].

同义名列表

35 个代谢物同义名

(2R,3S,3R,3aS,6S,6aS,6bS,7aR,11aS,1 1bR)-2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11a,11b-hexad ecahydro-3-hydroxy-3,6,10,11b-tetramethyl-Spiro[9H -benzo[a]fluorene-9,2(3H)-furo[3,2-b]pyridin]-11(1 H)-one; SPIRO(9H-BENZO(A)FLUORENE-9,2(3H)-FURO(3,2-B)PYRIDIN)-11(1H)-ONE, 2,3,3A,4,4,5,6,6,6A,6B,7,7,7A,8,11A,11B-HEXADECAHYDRO-3-HYDROXY-3,6,10,11B-TETRAMETHYL-, (2R,3S,3R,3AS,6S,6AS,6BS,7AR,11AS,11BR)-; (2R,3S,3R,3aS,6S,6aS,6bS,7aR,11aS,11bR)-2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11a,11b-hexadecahydro-3-hydroxy-3,6,10,11b-tetramethyl-Spiro[9H-benzo[a]fluorene-9,2(3H)-furo[3,2-b]pyridin]-11(1H)-one; (3S,3R,3aS,6S,6aS,6bS,7aR,9R,11aS,11bR)-3-hydroxy-3,6,10,11b-tetramethyl-spiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one; (3S,3R,3aS,6S,6aS,6bS,7aR,9R,11aS,11bR)-3-hydroxy-3,6,10,11b-tetramethylspiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-11-one; 5-hydroxy-2,3,6,15-tetramethyl-(1S,2R,2R,3R,3aS,5S,6S,7aR,10S,11S)-spiro[perhydrofuro[3,2-b]pyridine-2,14-tetracyclo[8.7.0.02,7.011,16]heptadeca-7,15-diene]-17-one; Spiro(9H-benzo(a)fluorene-9,2(3H)-furo(3,2-b)-pyridin)-11(1H)-one, 2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11a,11b-hexadecahydro-3-hydroxy-3,6,10, 11B-tetramethyl-; Spiro(9H-benzo(a)fluorene-9,2(3H)-furo(3,2-b)-pyridin)-11(1H)-one, 2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11a,11b-hexadecahydro-3-hydroxy- 3,6,10,11b-tetramethyl-; (3S,3R,3AS,6S,6aS,6bS,7aR,9R,11aS,11bR)-3-Hydroxy-3,6,10,11b-tetramethyl-spiro[1,2,3,4,6,6a,6b,7,8,11a-decahydrobenzo[a]fluorene-9,2-3a,4,5,6,7,7a-hexah; Spiro[9H-benzo[a]fluorene-9,2-b]-pyridin]-11(1H)-one,2,3,3a,4,4,5,6,6,6a,6b,7,7,7a,8,11a,11b-hexadecahydro-3-hydroxy-3,6,10,11b-tetramethyl-; Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3.beta.,23.beta.)-; WLN: L D6 B566 CV FX DU LUTJ A1 E1 OQ F-& CT56 BOX FMTJ D1 H1; Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3-beta,23-beta)-; Veratraman-11-one, 17,23-epoxy-3-hydroxy-, (3beta,23beta)-; Veratraman-11-one,23-epoxy-3-hydroxy-, (3.beta.,23.beta.)-; (3beta,23beta)-17,23-Epoxy-3-hydroxyveratraman-11-one; 17,23beta-Epoxy-3beta-hydroxyveratraman-11-one; 4-27-00-03590 (Beilstein Handbook Reference); jervine, acetate, (3beta,23beta)-isomer; 17,23-Epoxy-3-hydroxyveratraman-11-one; Jervine, >=98\\% (HPLC), powder; CLEXYFLHGFJONT-DNMILWOZSA-N; 11-Ketocyclopamine; Jerwiny [Polish]; UNII-19V3ECX465; JERVINE [HSDB]; Jervin-11-one; JERVINE [MI]; 19V3ECX465; C27H39NO3; Jervine; Jerwiny; Iervin; jervin; Jervine



数据库引用编号

15 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)

72 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, BCL2, CASP3, CD34, GLI1, LPIN1, LPO, MTOR, PIK3CA, PPARG, PRKAA2, SIRT1, SMO
Peripheral membrane protein 2 ANXA5, MTOR
Endoplasmic reticulum membrane 3 BCL2, LPIN1, MTOR
Nucleus 10 BCL2, CASP3, CEBPA, GLI1, LPIN1, MTOR, PPARG, PRKAA2, SIRT1, SMO
cytosol 11 ANXA5, BCL2, CASP3, GLI1, LPIN1, MTOR, PIK3CA, PPARG, PRKAA2, SIRT1, SMO
dendrite 3 MTOR, PRKAA2, SMO
phagocytic vesicle 1 MTOR
nucleoplasm 9 CASP3, CEBPA, GLI1, LPIN1, MTOR, PPARG, PRKAA2, SIRT1, SMO
RNA polymerase II transcription regulator complex 2 CEBPA, PPARG
Cell membrane 4 ABCB1, PTCH1, SMO, TNF
Cytoplasmic side 1 MTOR
lamellipodium 1 PIK3CA
Multi-pass membrane protein 3 ABCB1, PTCH1, SMO
Golgi apparatus membrane 1 MTOR
cell surface 3 ABCB1, ADIPOQ, TNF
glutamatergic synapse 1 CASP3
Golgi apparatus 2 PRKAA2, SMO
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
neuronal cell body 3 CASP3, PRKAA2, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 1 LPIN1
Lysosome 2 CD34, MTOR
plasma membrane 6 ABCB1, CD34, PIK3CA, PTCH1, SMO, TNF
Membrane 7 ABCB1, ANXA5, BCL2, CD34, MTOR, PRKAA2, PTCH1
apical plasma membrane 2 ABCB1, CD34
axon 2 CCK, PRKAA2
basolateral plasma membrane 1 LPO
caveola 1 PTCH1
extracellular exosome 5 ABCB1, ANXA5, LPO, RETN, SMO
Lysosome membrane 1 MTOR
endoplasmic reticulum 4 ADIPOQ, BCL2, LPIN1, SMO
extracellular space 5 ADIPOQ, CCK, LPO, RETN, TNF
perinuclear region of cytoplasm 4 CD34, PIK3CA, PPARG, PTCH1
intercalated disc 1 PIK3CA
mitochondrion 2 BCL2, SIRT1
protein-containing complex 1 BCL2
intracellular membrane-bounded organelle 4 CEBPA, PPARG, PTCH1, SMO
Microsome membrane 1 MTOR
postsynaptic density 1 CASP3
chromatin silencing complex 1 SIRT1
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 CD34
Secreted 4 ADIPOQ, CCK, LPO, RETN
extracellular region 7 ADIPOQ, ANXA5, CCK, CD34, LPO, RETN, TNF
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 3 BCL2, LPIN1, MTOR
transcription regulator complex 1 CEBPA
Cell projection, cilium 1 SMO
ciliary membrane 2 PTCH1, SMO
Nucleus membrane 2 BCL2, LPIN1
Bcl-2 family protein complex 1 BCL2
nuclear membrane 3 BCL2, LPIN1, SMO
external side of plasma membrane 3 ANXA5, CD34, TNF
nucleolus 2 CEBPA, SIRT1
midbody 1 PTCH1
apical part of cell 1 PTCH1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 PTCH1
Apical cell membrane 1 ABCB1
heterochromatin 1 SIRT1
Membrane raft 1 TNF
pore complex 1 BCL2
focal adhesion 1 ANXA5
collagen trimer 1 ADIPOQ
Nucleus, PML body 2 MTOR, SIRT1
PML body 2 MTOR, SIRT1
collagen-containing extracellular matrix 2 ADIPOQ, ANXA5
axoneme 1 GLI1
ciliary tip 2 GLI1, SMO
nuclear speck 1 PRKAA2
nuclear inner membrane 1 SIRT1
Late endosome 1 SMO
receptor complex 1 PPARG
Zymogen granule membrane 1 ANXA5
ciliary base 1 GLI1
cilium 1 SMO
chromatin 3 CEBPA, PPARG, SIRT1
axonal growth cone 1 PTCH1
phagocytic cup 1 TNF
centriole 1 SMO
intercellular bridge 1 CD34
fibrillar center 1 SIRT1
nuclear envelope 3 LPIN1, MTOR, SIRT1
Endomembrane system 1 MTOR
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 SIRT1
dendritic growth cone 1 PTCH1
myelin sheath 1 BCL2
basal plasma membrane 1 CD34
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
specific granule lumen 1 RETN
endocytic vesicle membrane 2 PTCH1, SMO
azurophil granule lumen 1 RETN
[Isoform 2]: Cytoplasm 1 GLI1
9+0 non-motile cilium 1 SMO
vesicle membrane 1 ANXA5
endoplasmic reticulum-Golgi intermediate compartment 1 SMO
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
nucleotide-activated protein kinase complex 1 PRKAA2
Cytoplasmic vesicle, phagosome 1 MTOR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
GLI-SUFU complex 1 GLI1
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
C/EBP complex 1 CEBPA
CHOP-C/EBP complex 1 CEBPA
glomerular endothelium fenestra 1 CD34
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Isoform 4]: Nucleus, nucleolus 1 CEBPA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1


文献列表

  • Song Wang, Jiali Cui, Gaoqiong Zhao, Hongbin Liu, Jingkun Wang. Pharmacokinetics of Veratramine and Jervine from Alcohol Extracts of Radix Veratri. Computational and mathematical methods in medicine. 2022; 2022(?):8289548. doi: 10.1155/2022/8289548. [PMID: 35785141]
  • Yue Cong, Yantong Wu, Shan Shen, Xiping Liu, Jinggong Guo. A Structure-Activity Relationship between the Veratrum Alkaloids on the Antihypertension and DNA Damage Activity in Mice. Chemistry & biodiversity. 2020 Feb; 17(2):e1900473. doi: 10.1002/cbdv.201900473. [PMID: 31961474]
  • Fadime Atalay Dumlu, Tuba Aydin, Fehmi Odabasoglu, Ozlem Aydin Berktas, Zerrin Kutlu, Huseyin Serkan Erol, Mesut B Halici, Elif Cadirci, Ahmet Cakir. Anti-inflammatory and antioxidant properties of jervine, a sterodial alkaloid from rhizomes of Veratrum album. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Mar; 55(?):191-199. doi: 10.1016/j.phymed.2018.06.035. [PMID: 30668429]
  • Elina Karhu, Janne Isojärvi, Pia Vuorela, Leena Hanski, Adyary Fallarero. Identification of Privileged Antichlamydial Natural Products by a Ligand-Based Strategy. Journal of natural products. 2017 10; 80(10):2602-2608. doi: 10.1021/acs.jnatprod.6b01052. [PMID: 29043803]
  • Kohei Kazuma, Katsuhiro Konno. [Poisoning by accidental ingestion of poisonous plants]. Chudoku kenkyu : Chudoku Kenkyukai jun kikanshi = The Japanese journal of toxicology. 2013 Jun; 26(2):97-101. doi: ". [PMID: 23855239]
  • Lamia Ghezali, David Yannick Leger, Youness Limami, Jeanne Cook-Moreau, Jean-Louis Beneytout, Bertrand Liagre. Cyclopamine and jervine induce COX-2 overexpression in human erythroleukemia cells but only cyclopamine has a pro-apoptotic effect. Experimental cell research. 2013 Apr; 319(7):1043-53. doi: 10.1016/j.yexcr.2013.01.014. [PMID: 23357584]
  • Jana Balbuena, Gisela Pachon, Guillermo Lopez-Torrents, Josep M Aran, Javier S Castresana, Jordi Petriz. ABCG2 is required to control the sonic hedgehog pathway in side population cells with stem-like properties. Cytometry. Part A : the journal of the International Society for Analytical Cytology. 2011 Sep; 79(9):672-83. doi: 10.1002/cyto.a.21103. [PMID: 21774076]
  • Jian-Liang Zhou, Gui-Zhong Xin, Zi-Qi Shi, Mei-Ting Ren, Lian-Wen Qi, Hui-Jun Li, Ping Li. Characterization and identification of steroidal alkaloids in Fritillaria species using liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of chromatography. A. 2010 Nov; 1217(45):7109-22. doi: 10.1016/j.chroma.2010.09.019. [PMID: 20926090]
  • L K Bechtel, D T Lawrence, D Haverstick, J S Powers, S A Wyatt, T Croley, C P Holstege. Ingestion of false hellebore plants can cross-react with a digoxin clinical chemistry assay. Clinical toxicology (Philadelphia, Pa.). 2010 Jun; 48(5):435-42. doi: 10.3109/15563651003733666. [PMID: 20586573]
  • Jian Tang, Hui-Liang Li, Yun-Heng Shen, Hui-Zi Jin, Shi-Kai Yan, Xiao-Hua Liu, Hua-Wu Zeng, Run-Hui Liu, Ye-Xiong Tan, Wei-Dong Zhang. Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum. Phytotherapy research : PTR. 2010 Jun; 24(6):821-6. doi: 10.1002/ptr.3022. [PMID: 20013819]
  • T Grobosch, T Binscheck, F Martens, D Lampe. Accidental intoxication with Veratrum album. Journal of analytical toxicology. 2008 Nov; 32(9):768-73. doi: 10.1093/jat/32.9.768. [PMID: 19021933]
  • Jian Tang, Hui-Liang Li, Yun-Heng Shen, Hui-Zi Jin, Shi-Kai Yan, Run-Hui Liu, Wei-Dong Zhang. Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum. Phytotherapy research : PTR. 2008 Aug; 22(8):1093-6. doi: 10.1002/ptr.2463. [PMID: 18570211]
  • Yue Cong, Jin-Hui Wang, Rui Wang, Yi-Mei Zeng, Chang-Da Liu, Xian Li. A study on the chemical constituents of Veratrum nigrum L. processed by rice vinegar. Journal of Asian natural products research. 2008 Jul; 10(7-8):619-24. doi: 10.1080/10286020802133266. [PMID: 18636372]
  • Sheng Zhang, Jianxia Zhou, Qingyao Shou, Ying Peng, Zhengwu Shen. [Determination of jervine and veratramine in Veratrum plants using high performance liquid chromatography coupled with evaporative light scattering detection]. Se pu = Chinese journal of chromatography. 2008 Jan; 26(1):56-9. doi: . [PMID: 18438025]
  • Kap-Rang Lee, Nobuyuki Kozukue, Jae-Sook Han, Joon-Hong Park, Eun-Young Chang, Eun-Jung Baek, Jong-Sun Chang, Mendel Friedman. Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. Journal of agricultural and food chemistry. 2004 May; 52(10):2832-9. doi: 10.1021/jf030526d. [PMID: 15137822]
  • Stephen T Lee, Kip E Panter, William Gaffield, Bryan L Stegelmeier. Development of an enzyme-linked immunosorbent assay for the veratrum plant teratogens: cyclopamine and jervine. Journal of agricultural and food chemistry. 2003 Jan; 51(3):582-6. doi: 10.1021/jf020961s. [PMID: 12537426]
  • R K Mann, P A Beachy. Cholesterol modification of proteins. Biochimica et biophysica acta. 2000 Dec; 1529(1-3):188-202. doi: 10.1016/s1388-1981(00)00148-7. [PMID: 11111088]
  • T Fukushima. [Monoamine oxidase (XXXVI). Characteristics of benzylamine oxidase in the dog serum]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica. 1975 Jul; 71(5):457-62. doi: . [PMID: 280]