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MedKoo Cat#: 592232 | Name: Heliotrine
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Description:

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

Heliotrine is a pyrrolizidine alkaloid found in plants of the Boraginaceae and Asteraceae families, known for its hepatotoxic and genotoxic effects. It undergoes metabolic activation in the liver via cytochrome P450 enzymes, forming pyrrolic metabolites that cause DNA adduct formation, hepatocellular damage, and veno-occlusive disease.

Chemical Structure

Heliotrine
Heliotrine
CAS# 303-33-3

Theoretical Analysis

MedKoo Cat#: 592232

Name: Heliotrine

CAS#: 303-33-3

Chemical Formula: C16H27NO5

Exact Mass: 313.1889

Molecular Weight: 313.39

Elemental Analysis: C, 61.32; H, 8.68; N, 4.47; O, 25.53

Price and Availability

Size Price Availability Quantity
10mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Heliotrine; 7S-Heliotrine; (+)-Heliotrine; Heliotrine, (+)-
IUPAC/Chemical Name
((1S,7aR)-1-hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl)methyl (2S,3R)-2-hydroxy-2-isopropyl-3-methoxybutanoate
InChi Key
LMFKRLGHEKVMNT-UJDVCPFMSA-N
InChi Code
InChI=1S/C16H27NO5/c1-10(2)16(20,11(3)21-4)15(19)22-9-12-5-7-17-8-6-13(18)14(12)17/h5,10-11,13-14,18,20H,6-9H2,1-4H3/t11-,13+,14-,16+/m1/s1
SMILES Code
CC(C)[C@@]([C@H](OC)C)(O)C(OCC1=CCN2[C@@]1([H])[C@@H](O)CC2)=O
Appearance
Solid powder
Purity
>85% (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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 313.39 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
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Disturbance of gene expression in primary human hepatocytes by hepatotoxic pyrrolizidine alkaloids: A whole genome transcriptome analysis. Toxicol In Vitro. 2015 Oct;29(7):1669-82. doi: 10.1016/j.tiv.2015.06.021. Epub 2015 Jun 20. PubMed PMID: 26100227. 5: Field RA, Stegelmeier BL, Colegate SM, Brown AW, Green BT. An in vitro comparison of the cytotoxic potential of selected dehydropyrrolizidine alkaloids and some N-oxides. Toxicon. 2015 Apr;97:36-45. doi: 10.1016/j.toxicon.2015.02.001. Epub 2015 Feb 7. PubMed PMID: 25666399. 6: Shimshoni JA, Mulder PP, Bouznach A, Edery N, Pasval I, Barel S, Abd-El Khaliq M, Perl S. Heliotropium europaeum poisoning in cattle and analysis of its pyrrolizidine alkaloid profile. J Agric Food Chem. 2015 Feb 11;63(5):1664-72. doi: 10.1021/jf5052199. Epub 2015 Jan 27. PubMed PMID: 25591008. 7: Zhao Y, Wang S, Xia Q, Gamboa da Costa G, Doerge DR, Cai L, Fu PP. Reaction of dehydropyrrolizidine alkaloids with valine and hemoglobin. Chem Res Toxicol. 2014 Oct 20;27(10):1720-31. doi: 10.1021/tx5002139. Epub 2014 Sep 11. PubMed PMID: 25211425. 8: Hessel S, Gottschalk C, Schumann D, These A, Preiss-Weigert A, Lampen A. Structure-activity relationship in the passage of different pyrrolizidine alkaloids through the gastrointestinal barrier: ABCB1 excretes heliotrine and echimidine. Mol Nutr Food Res. 2014 May;58(5):995-1004. doi: 10.1002/mnfr.201300707. Epub 2013 Dec 27. PubMed PMID: 24375927. 9: Oplatowska M, Elliott CT, Huet AC, McCarthy M, Mulder PP, von Holst C, Delahaut P, Van Egmond HP, Campbell K. Development and validation of a rapid multiplex ELISA for pyrrolizidine alkaloids and their N-oxides in honey and feed. Anal Bioanal Chem. 2014 Jan;406(3):757-70. doi: 10.1007/s00216-013-7488-7. Epub 2013 Dec 11. PubMed PMID: 24327075. 10: Xia Q, Zhao Y, Von Tungeln LS, Doerge DR, Lin G, Cai L, Fu PP. Pyrrolizidine alkaloid-derived DNA adducts as a common biological biomarker of pyrrolizidine alkaloid-induced tumorigenicity. Chem Res Toxicol. 2013 Sep 16;26(9):1384-96. doi: 10.1021/tx400241c. Epub 2013 Aug 26. PubMed PMID: 23937665. 11: Tamta H, Pawar RS, Wamer WG, Grundel E, Krynitsky AJ, Rader JI. Comparison of metabolism-mediated effects of pyrrolizidine alkaloids in a HepG2/C3A cell-S9 co-incubation system and quantification of their glutathione conjugates. Xenobiotica. 2012 Oct;42(10):1038-48. doi: 10.3109/00498254.2012.679978. Epub 2012 Apr 23. PubMed PMID: 22519982. 12: Xia Q, Yan J, Chou MW, Fu PP. Formation of DHP-derived DNA adducts from metabolic activation of the prototype heliotridine-type pyrrolizidine alkaloid, heliotrine. Toxicol Lett. 2008 May 5;178(2):77-82. doi: 10.1016/j.toxlet.2008.02.008. Epub 2008 Mar 4. PubMed PMID: 18395999. 13: Cosmetic Ingredient Review Expert Panel. Final report of the safety assessment of niacinamide and niacin. Int J Toxicol. 2005;24 Suppl 5:1-31. Review. PubMed PMID: 16596767. 14: Sanderson BJ, Clark AM. Micronuclei in adult and foetal mice exposed in vivo to heliotrine, urethane, monocrotaline and benzidine. Mutat Res. 1993 Jan;285(1):27-33. PubMed PMID: 7678129. 15: Moore DJ, Batts KP, Zalkow LL, Fortune GT Jr, Powis G. Model systems for detecting the hepatic toxicity of pyrrolizidine alkaloids and pyrrolizidine alkaloid N-oxides. Toxicol Appl Pharmacol. 1989 Nov;101(2):271-84. PubMed PMID: 2815083. 16: Lieber MM, Ames MM, Powis G, Kovach JS. Anticancer drug testing in vitro: use of an activating system with the human tumor stem cell assay. Life Sci. 1981 Jan 19;28(3):287-93. PubMed PMID: 7219049. 17: Peterson JE, Jago MV. Comparison of the toxic effects of dehydroheliotridine and heliotrine in pregnant rats and their embryos. J Pathol. 1980 Aug;131(4):339-55. PubMed PMID: 7431152. 18: Evans JV, Daley SK, McClusky GA, Nielsen CJ. Direct quantitative analysis of indicine-N-oxide in cancer patient samples by gas chromatography using the internal standard heliotrine-N-oxide including a mass spectral comparison of their trimethylsilyl derivatives. Biomed Mass Spectrom. 1980 Feb;7(2):65-73. PubMed PMID: 7407334. 19: Powis G, Ames MM, Kovach JS. Relationship of the reductive metabolism of indicine N-oxide to its antitumor activity. Res Commun Chem Pathol Pharmacol. 1979 Jun;24(3):559-69. PubMed PMID: 451340. 20: Evans JV, Peng A, Nielsen CJ. The gas chromatographic mass spectrometric analysis of the new antitumor drug indicine-N-oxide utilizing a novel reaction accompanying trimethylsilylation. Biomed Mass Spectrom. 1979 Jan;6(1):38-43. PubMed PMID: 427260.