Isocolumbin (BioDeep_00000000363)

 

Secondary id: BioDeep_00000403163, BioDeep_00001870311

human metabolite PANOMIX_OTCML-2023 Endogenous natural product PANOMIX_OTCML-2025


Metabolite Card


1,4-Etheno-3H,7H-benzo[1,2-c:3,4-c]dipyran-3,7-dione, 9-(3-furanyl)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4-hydroxy-4a,10a-dimethyl-, [1R-(1.alpha.,4.beta.,4a.alpha.,6a.beta.,9.beta.,10a.beta.,10b.alpha.)]-

  Formula: C20H22O6 (358.1416)
Chinese Names: 异古伦宾, 古伦宾, 青牛胆苦素, 咖伦宾
  Spectrum Hits: Top Source Viridiplantae(otcml) 34.33%

Reviewed

Last reviewed on 2025-06-03.

Cite this Page

Isocolumbin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/isocolumbin (retrieved 2025-12-05) (BioDeep RN: BioDeep_00000000363). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Molecular Structure

SMILES: CC12CC(c3ccoc3)OC(=O)C1CCC1(C)C2C2C=CC1(O)C(=O)O2
InChI: InChI=1S/C20H22O6/c1-18-9-14(11-5-8-24-10-11)25-16(21)12(18)3-6-19(2)15(18)13-4-7-20(19,23)17(22)26-13/h4-5,7-8,10,12-15,23H,3,6,9H2,1-2H3


Description

Isocolumbin is found in fruits. Isocolumbin is isolated from Dioscoreophyllum cumminsii (serendipity berry).
Isolated from Dioscoreophyllum cumminsii (serendipity berry). Isocolumbin is found in fruits.
Columbin is a natural product found in Tinospora capillipes and Cleidion with data available.
Columbin is an organic heterotricyclic compound and an organooxygen compound.
(2S,4AR,6aR,7R,10R,10aS,10bS)-2-(furan-3-yl)-7-hydroxy-6a,10b-dimethyl-4a,5,6,6a,7,10,10a,10b-octahydro-1H-10,7-(epoxymethano)benzo[f]isochromene-4,12(2H)-dione is a natural product found in Vateria indica, Penianthus zenkeri, and other organisms with data available.
Columbin is an orally active diterpenoid furanolactone from Calumbae radix, has anti-inflammatory and anti-trypanosomal effects. Columbin selectively inhibits COX-2 (EC50=53.1 μM) over COX-1 (EC50=327 μM)[1][2].
Columbin is an orally active diterpenoid furanolactone from Calumbae radix, has anti-inflammatory and anti-trypanosomal effects. Columbin selectively inhibits COX-2 (EC50=53.1 μM) over COX-1 (EC50=327 μM)[1][2].

Synonyms

19 synonym names

1,4-Etheno-3H,7H-benzo[1,2-c:3,4-c]dipyran-3,7-dione, 9-(3-furanyl)-1,4,4a,5,6,6a,9,10,10a,10b-decahydro-4-hydroxy-4a,10a-dimethyl-, [1R-(1.alpha.,4.beta.,4a.alpha.,6a.beta.,9.beta.,10a.beta.,10b.alpha.)]-; 1,4-Etheno-3H,7H-benzo[1,2-c:3,4-c]dipyran-3,7-dione, 9-(3-furanyl)decahydro-4-hydroxy-4a,10a-dimethyl-, [1R-(1.alpha.,4.beta.,4a.alpha.,6a.beta.,9.beta.,10a.beta.,10b.alpha.)]-; 17,18-Dinor-8.beta.H,9.beta.H,10.alpha.-labda-2,13(16),14-triene-19,20-dioic acid, 15,16-epoxy-1.beta.,4,12-trihydroxy-5,9-dimethyl-, 19,1:20,12-dilactone; (1S,2R,3R,5R,8R,11S,12S)-5-(furan-3-yl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.02,11.03,8]hexadec-15-ene-7,13-dione; 5-(furan-3-yl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.02,11.03,8]hexadec-15-ene-7,13-dione; 5-(furan-3-yl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.0²,¹¹.0³,⁸]hexadec-15-ene-7,13-dione; 4-hydroxy-15,16-epoxycleroda-2,13(16),14-trieno-17,12-18,1-biscarbolactone; AALLCALQGXXWNA-UHFFFAOYSA-N; Isocolumbin; Columbin; (2S,4AR,6aR,7R,10R,10aS,10bS)-2-(furan-3-yl)-7-hydroxy-6a,10b-dimethyl-4a,5,6,6a,7,10,10a,10b-octahydro-1H-10,7-(epoxymethano)benzo[f]isochromene-4,12(2H)-dione; 2-(Furan-3-yl)-7-hydroxy-6a,10b-dimethyl-1,2,4a,5,6,6a,7,10,10a,10b-decahydro-4H-10,7-(epoxymethano)naphtho[2,1-c]pyran-4,12-dione; (1R,2S,3S,5S,8R,11R,12R)-5-(Furan-3-yl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.02,11.03,8]hexadec-15-ene-7,13-dione; Columbin, >=95\\% (LC/MS-ELSD); Columbin; Columbin; Columbin (Standard); Columbin, >=95% (LC/MS-ELSD); (1S,2S,3S,5S,8S,11R,12S)-5-(Furan-3-yl)-12-hydroxy-3,11-dimethyl-6,14-dioxatetracyclo[10.2.2.02,11.03,8]hexadec-15-ene-7,13-dione



Cross Reference

32 cross reference id

Classification Terms

Related Pathways

Reactome()

BioCyc()

PlantCyc()

Biological Process

related biological process reactions.

Reactome()

BioCyc()

WikiPathways()

Plant Reactome()

INOH()

PlantCyc()

COVID-19 Disease Map()

PathBank()

PharmGKB()

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。

Sub-cellular location Genes
Cytoplasm 8 AKR1B1, CYP3A4, EGFR, FES, MAPK8, NFKB1, PTGS1, PTGS2
Peripheral membrane protein 3 CYP1B1, PTGS1, PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 5 CYP1B1, CYP3A4, EGFR, PTGS1, PTGS2
Nucleus 5 EGFR, LMNA, MAPK8, NFKB1, NR1I2
cytosol 7 AKR1B1, FES, GPT, LMNA, MAPK8, NFKB1, SOCS3
nuclear body 1 NR1I2
nucleoplasm 5 AKR1B1, LMNA, MAPK8, NFKB1, NR1I2
Cell membrane 3 CD8A, EGFR, EPHA2
lamellipodium 1 EPHA2
ruffle membrane 2 EGFR, EPHA2
Early endosome membrane 1 EGFR
Synapse 1 MAPK8
cell junction 1 EGFR
cell surface 3 ADIPOQ, EGFR, EPHA2
glutamatergic synapse 1 EGFR
Golgi apparatus 2 FES, PTGS1
Golgi membrane 1 EGFR
lysosomal membrane 1 GAA
Lysosome 1 GAA
endosome 1 EGFR
plasma membrane 6 CD8A, EGFR, EPHA2, FES, GAA, IFNLR1
Membrane 7 CYP1B1, CYP3A4, EGFR, EPHA2, FES, GAA, IFNLR1
apical plasma membrane 1 EGFR
axon 1 MAPK8
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 6 AKR1B1, AMY2A, CETP, GAA, GPT, PTGS1
Lysosome membrane 1 GAA
endoplasmic reticulum 2 ADIPOQ, PTGS2
extracellular space 5 ADIPOQ, AKR1B1, AMY2A, CETP, EGFR
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 EGFR, LMNA
mitochondrion 3 AKR1B1, CYP1B1, NFKB1
protein-containing complex 2 EGFR, PTGS2
intracellular membrane-bounded organelle 4 CYP1B1, CYP3A4, GAA, PTGS1
Microsome membrane 4 CYP1B1, CYP3A4, PTGS1, PTGS2
Single-pass type I membrane protein 4 CD8A, EGFR, EPHA2, IFNLR1
Secreted 3 ADIPOQ, CETP, GAA
extracellular region 6 ADIPOQ, AMY2A, CD8A, CETP, GAA, NFKB1
cytoplasmic side of plasma membrane 2 FES, SOCS3
Single-pass membrane protein 1 EPHA2
[Isoform 2]: Secreted 1 CD8A
transcription regulator complex 2 NFKB1, NR1I2
photoreceptor outer segment 1 PTGS1
nuclear membrane 2 EGFR, LMNA
external side of plasma membrane 1 CD8A
high-density lipoprotein particle 1 CETP
cytoplasmic vesicle 1 FES
microtubule cytoskeleton 1 FES
vesicle 1 CETP
Cell projection, ruffle membrane 1 EPHA2
Membrane raft 1 EGFR
Cell junction, focal adhesion 1 EPHA2
Cytoplasm, cytoskeleton 1 FES
focal adhesion 3 EGFR, EPHA2, FES
collagen trimer 1 ADIPOQ
intracellular vesicle 1 EGFR
collagen-containing extracellular matrix 1 ADIPOQ
intermediate filament 1 LMNA
nuclear speck 1 LMNA
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 3 CD8A, EGFR, EPHA2
neuron projection 2 PTGS1, PTGS2
chromatin 2 NFKB1, NR1I2
cytoskeleton 1 FES
site of double-strand break 1 LMNA
nuclear envelope 1 LMNA
Nucleus envelope 1 LMNA
Endomembrane system 1 PTGS1
leading edge membrane 1 EPHA2
Nucleus, nucleoplasm 1 LMNA
tertiary granule membrane 1 GAA
intermediate filament cytoskeleton 1 NR1I2
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
plasma membrane raft 1 CD8A
secretory granule lumen 1 NFKB1
endoplasmic reticulum lumen 1 PTGS2
nuclear matrix 1 LMNA
phosphatidylinositol 3-kinase complex 1 SOCS3
specific granule lumen 1 NFKB1
azurophil granule membrane 1 GAA
tight junction 1 EPHA2
Nucleus matrix 1 LMNA
nuclear lamina 1 LMNA
clathrin-coated endocytic vesicle membrane 1 EGFR
ficolin-1-rich granule membrane 1 GAA
basal dendrite 1 MAPK8
[Isoform 1]: Cell membrane 1 CD8A
lamellipodium membrane 1 EPHA2
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
T cell receptor complex 1 CD8A
Nucleus lamina 1 LMNA
[Isoform C]: Nucleus speckle 1 LMNA
lamin filament 1 LMNA
Cell projection, lamellipodium membrane 1 EPHA2
autolysosome lumen 1 GAA
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
interleukin-28 receptor complex 1 IFNLR1


Literature Reference

  • Yufen Liao, Xin Wang, Guangyun Ran, Shiyu Zhang, Chutian Wu, Rong Tan, Ying Liu, Yan He, Ting Liu, Zhongxiu Wu, Ying Peng, Weiwei Li, Jiang Zheng. DNA damage and up-regulation of PARP-1 induced by columbin in vitro and in vivo. Toxicology letters. 2023 Mar; 379(?):20-34. doi: 10.1016/j.toxlet.2023.03.003. [PMID: 36905973]
  • Murugammal Shanmugam, Subashini Subramanian, Shakila Ramachandran. Method development and validation for quantification of six bioactive compounds (andrographolide, columbin, piperine, gallic, paracoumaric and oleanolic acids) by HPTLC. Journal of complementary & integrative medicine. 2022 Nov; ?(?):. doi: 10.1515/jcim-2022-0135. [PMID: 36384045]
  • Pooja M, Gangavaram Jyothi Reddy, Kanipakam Hema, Sujatha Dodoala, Bharathi Koganti. Unravelling high-affinity binding compounds towards transmembrane protease serine 2 enzyme in treating SARS-CoV-2 infection using molecular modelling and docking studies. European journal of pharmacology. 2021 Jan; 890(?):173688. doi: 10.1016/j.ejphar.2020.173688. [PMID: 33130280]
  • Jiaping Pei, Wen Xiao, Danyan Zhu, Xiaowei Ji, Liping Shi, Xiaozhao Deng. Cytochrome P450 Enzyme-Mediated Bioactivation as an Underlying Mechanism of Columbin-Induced Hepatotoxicity. Chemical research in toxicology. 2020 04; 33(4):940-947. doi: 10.1021/acs.chemrestox.9b00486. [PMID: 32162908]
  • Siddig Ibrahim Abdelwahab, Waleed Syaed Koko, Manal Mohamed Elhassan Taha, Syam Mohan, Mouna Achoui, Mahmood Ameen Abdulla, Mohd Rais Mustafa, Syahida Ahmad, Mohamed Ibrahim Noordin, Chung Lip Yong, Mohd Roslan Sulaiman, Rozana Othman, Asfarina Amir Hassan. In vitro and in vivo anti-inflammatory activities of columbin through the inhibition of cycloxygenase-2 and nitric oxide but not the suppression of NF-κB translocation. European journal of pharmacology. 2012 Mar; 678(1-3):61-70. doi: 10.1016/j.ejphar.2011.12.024. [PMID: 22227329]
  • Qirong Shi, Mingjin Liang, Weidong Zhang, Chuan Zhang, Runhui Liu, Yunheng Shen, Huiliang Li, Xiaolin Wang, Xiangwei Wang, Qiongqun Pan, Chunlin Chen. Quantitative LC/MS/MS method and pharmacokinetic studies of columbin, an anti-inflammation furanoditerpen isolated from Radix Tinosporae. Biomedical chromatography : BMC. 2007 Jun; 21(6):642-8. doi: 10.1002/bmc.802. [PMID: 17345572]
  • K Wada, T Kurihara, M Yagi, R Kobayashi, H Kaminaga, K Toi, M Haga. Columbin isolated from calumbae radix affects the sleeping time of anesthetized mice. Biological & pharmaceutical bulletin. 1995 Apr; 18(4):634-6. doi: 10.1248/bpb.18.634. [PMID: 7655444]