MedKoo Cat#: 145226 | Name: Andrograpanin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Andrograpanin is a hydrolysate from neoandrographolide. Andrograpanin is a compound of Andrographis paniculata, which has an important role in many inflammatory diseases, but the molecular mechanism of andrograpanin to combat inflammation is unclear. Andrograpanin inhibits the IκBα degradation and p65 phosphorylation in LPS-stimulated bEECs and LPS-induced endometrial injury. Studies show that andrograpanin might have therapeutic effects against endometritis.

Chemical Structure

Andrograpanin
Andrograpanin
CAS#82209-74-3

Theoretical Analysis

MedKoo Cat#: 145226

Name: Andrograpanin

CAS#: 82209-74-3

Chemical Formula: C20H30O3

Exact Mass: 318.2195

Molecular Weight: 318.46

Elemental Analysis: C, 75.43; H, 9.50; O, 15.07

Price and Availability

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1mg USD 450.00 2 Weeks
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Related CAS #
No Data
Synonym
Andrograpanin;
IUPAC/Chemical Name
3-(2-((1R,4aS,5R,8aS)-5-(hydroxymethyl)-5,8a-dimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)furan-2(5H)-one
InChi Key
WKKBRRFSRMDTJB-JYBIWHBTSA-N
InChi Code
1S/C20H30O3/c1-14-5-8-17-19(2,13-21)10-4-11-20(17,3)16(14)7-6-15-9-12-23-18(15)22/h9,16-17,21H,1,4-8,10-13H2,2-3H3/t16-,17-,19+,20+/m1/s1
SMILES Code
[H][C@]12CCC(=C)[C@@H](CCC3=CCOC3=O)[C@]1(C)CCC[C@@]2(C)CO
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 318.46 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Yin B, Umar T, Ma X, Chen Y, Umar Z, Umer S, Deng G. Andrograpanin mitigates lipopolysaccharides induced endometritis via TLR4/NF-κB pathway. Reprod Biol. 2022 Mar;22(1):100606. doi: 10.1016/j.repbio.2022.100606. Epub 2022 Jan 20. PMID: 35066371. 2: Liu J, Wang ZT, Ge BX. Andrograpanin, isolated from Andrographis paniculata, exhibits anti-inflammatory property in lipopolysaccharide-induced macrophage cells through down-regulating the p38 MAPKs signaling pathways. Int Immunopharmacol. 2008 Jul;8(7):951-8. doi: 10.1016/j.intimp.2007.12.014. Epub 2008 Jan 17. PMID: 18486905. 3: Ji LL, Wang Z, Dong F, Zhang WB, Wang ZT. Andrograpanin, a compound isolated from anti-inflammatory traditional Chinese medicine Andrographis paniculata, enhances chemokine SDF-1alpha-induced leukocytes chemotaxis. J Cell Biochem. 2005 Aug 1;95(5):970-8. doi: 10.1002/jcb.20464. PMID: 15937916. 4: Majumdar M, Dubey A, Goswami R, Misra TK, Roy DN. In vitro and in silico studies on the structural and biochemical insight of anti-biofilm activity of andrograpanin from Andrographis paniculata against Pseudomonas aeruginosa. World J Microbiol Biotechnol. 2020 Aug 27;36(10):143. doi: 10.1007/s11274-020-02919-x. PMID: 32851551. 5: Hanh TTH, My NTT, Cham PT, Quang TH, Cuong NX, Huong TT, Nam NH, Minh CV. Diterpenoids and Flavonoids from Andrographis paniculata. Chem Pharm Bull (Tokyo). 2020;68(1):96-99. doi: 10.1248/cpb.c19-00662. PMID: 31902905. 6: Wang KH, Zhang YT, Yang XW, Xu W, Zhang P, Gong Y, Liu NF. [Chemical constituents from Fukeqianjin formula]. Zhongguo Zhong Yao Za Zhi. 2018 Jun;43(11):2300-2312. Chinese. doi: 10.19540/j.cnki.cjcmm.20180408.006. PMID: 29945383. 7: Shivashankar S, Sangeetha MK. The Natural Ligand for Metalloproteinase-A Multifaceted Drug Target. Appl Biochem Biotechnol. 2022 Apr;194(4):1716-1739. doi: 10.1007/s12010-021-03778-4. Epub 2022 Jan 8. PMID: 34997448. 8: Srivastava P, Garg A, Misra RC, Chanotiya CS, Ghosh S. UGT86C11 is a novel plant UDP-glycosyltransferase involved in labdane diterpene biosynthesis. J Biol Chem. 2021 Sep;297(3):101045. doi: 10.1016/j.jbc.2021.101045. Epub 2021 Aug 4. PMID: 34363833; PMCID: PMC8427245. 9: Majumdar M, Singh V, Misra TK, Roy DN. In silico studies on structural inhibition of SARS-CoV-2 main protease Mpro by major secondary metabolites of Andrographis paniculata and Cinchona officinalis. Biologia (Bratisl). 2022;77(5):1373-1389. doi: 10.1007/s11756-022-01012-y. Epub 2022 Feb 28. PMID: 35250036; PMCID: PMC8883239. 10: Deiva Suga SS, Krishna Mohan S, Sreekandan RN, K M, Kamaraj D, Veeraraghavan VP, Jayaraman S, Rajagopal P. Molecular docking analysis of phytocompounds from Andrographis paniculata binding with proteins in the notch-signaling pathway. Bioinformation. 2020 Nov 30;16(11):923-928. doi: 10.6026/97320630016923. PMID: 34803268; PMCID: PMC8573459. 11: Sun W, Leng L, Yin Q, Xu M, Huang M, Xu Z, Zhang Y, Yao H, Wang C, Xiong C, Chen S, Jiang C, Xie N, Zheng X, Wang Y, Song C, Peters RJ, Chen S. The genome of the medicinal plant Andrographis paniculata provides insight into the biosynthesis of the bioactive diterpenoid neoandrographolide. Plant J. 2019 Mar;97(5):841-857. doi: 10.1111/tpj.14162. Epub 2019 Jan 2. Erratum in: Plant J. 2019 Mar;97(5):996. doi: 10.1111/tpj.14307. PMID: 30444296; PMCID: PMC7252214. 12: Li Y, Lin HX, Wang J, Yang J, Lai CJ, Wang X, Ma BW, Tang JF, Li Y, Li XL, Guo J, Gao W, Huang LQ. Glucosyltransferase Capable of Catalyzing the Last Step in Neoandrographolide Biosynthesis. Org Lett. 2018 Oct 5;20(19):5999-6002. doi: 10.1021/acs.orglett.8b02146. Epub 2018 Sep 20. PMID: 30234309. 13: Roy A. Molecular docking analysis of compounds from Andrographis paniculata with EGFR. Bioinformation. 2021 Jan 31;17(1):23-28. doi: 10.6026/97320630017023. PMID: 34393414; PMCID: PMC8340687. 14: Adiguna SP, Panggabean JA, Swasono RT, Rahmawati SI, Izzati F, Bayu A, Putra MY, Formisano C, Giuseppina C. Evaluations of Andrographolide-Rich Fractions of Andrographis paniculata with Enhanced Potential Antioxidant, Anticancer, Antihypertensive, and Anti-Inflammatory Activities. Plants (Basel). 2023 Mar 7;12(6):1220. doi: 10.3390/plants12061220. PMID: 36986909; PMCID: PMC10052505. 15: Reddy VL, Reddy SM, Ravikanth V, Krishnaiah P, Goud TV, Rao TP, Ram TS, Gonnade RG, Bhadbhade M, Venkateswarlu Y. A new bis-andrographolide ether from Andrographis paniculata nees and evaluation of anti-HIV activity. Nat Prod Res. 2005 Apr;19(3):223-30. doi: 10.1080/14786410410001709197. PMID: 15702635. 16: Kumar S, Dhanani T, Shah S. Extraction of three bioactive diterpenoids from Andrographis paniculata: effect of the extraction techniques on extract composition and quantification of three andrographolides using high-performance liquid chromatography. J Chromatogr Sci. 2014 Oct;52(9):1043-50. doi: 10.1093/chromsci/bmt157. Epub 2013 Oct 29. PMID: 24170124. 17: Xu C, Wang ZT. [Chemical constituents from roots of Andrographis paniculata]. Yao Xue Xue Bao. 2011 Mar;46(3):317-21. Chinese. PMID: 21626787. 18: Aishvarya Rukmani P, Shanmugam R, Manigandan P. Anti-Inflammatory Effect of Herbal Mouthwash Prepared Using Andrographis Paniculata and Rosa Formulation. J Pharm Bioallied Sci. 2024 Apr;16(Suppl 2):S1345-S1349. doi: 10.4103/jpbs.jpbs_581_23. Epub 2024 Apr 16. PMID: 38882775; PMCID: PMC11174168. 19: Chao WW, Lin BF. Isolation and identification of bioactive compounds in Andrographis paniculata (Chuanxinlian). Chin Med. 2010 May 13;5:17. doi: 10.1186/1749-8546-5-17. PMID: 20465823; PMCID: PMC2881933. 20: Bhaskar Reddy MV, Kishore PH, Rao CV, Gunasekar D, Caux C, Bodo B. New 2'-oxygenated flavonoids from Andrographis affinis. J Nat Prod. 2003 Feb;66(2):295-7. doi: 10.1021/np020331k. PMID: 12608871.