MedKoo Cat#: 462888 | Name: Ambiguine

Description:

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

Ambiguine is an antimicrobial alkaloid.

Chemical Structure

Ambiguine
Ambiguine
CAS#68388-52-3

Theoretical Analysis

MedKoo Cat#: 462888

Name: Ambiguine

CAS#: 68388-52-3

Chemical Formula: C28H45NO8

Exact Mass: 523.3145

Molecular Weight: 523.67

Elemental Analysis: C, 64.22; H, 8.66; N, 2.67; O, 24.44

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
Ambiguine;
IUPAC/Chemical Name
1-ethyl-6,12-dihydroxy-10,11a,13-trimethoxy-3-(2-methoxyethyl)tetradecahydro-2H-3,6a,12-(epiethane[1,1,2]triyl)-7,9-methanonaphtho[2,3-b]azocin-8-yl acetate
InChi Key
PZQUJIBUDVFDII-UHFFFAOYSA-N
InChi Code
InChI=1S/C28H45NO8/c1-7-29-14-25(10-11-33-3)9-8-19(31)27-17-12-16-18(34-4)13-26(36-6,20(17)21(16)37-15(2)30)28(32,24(27)29)23(35-5)22(25)27/h16-24,31-32H,7-14H2,1-6H3
SMILES Code
CCN1CC2(CCC(C34C5CC6C(OC)CC(C5C6OC(C)=O)(C(C(C23)OC)(C14)O)OC)O)CCOC
Appearance
Solid powder
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
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 523.67 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: Hu J, Lyu T, Cai J, Gao X, Zhang LF, Jing NH, Peng TF, Shi JY, Hao SH. [C_(19)-diterpenoid alkaloids from Aconitum austroyunnanense]. Zhongguo Zhong Yao Za Zhi. 2019 Feb;44(4):717-722. Chinese. doi: 10.19540/j.cnki.cjcmm.20180808.001. PMID: 30989884. 2: Xu J, Rawal VH. Total Synthesis of (-)-Ambiguine P. J Am Chem Soc. 2019 Mar 27;141(12):4820-4823. doi: 10.1021/jacs.9b01739. Epub 2019 Mar 13. PMID: 30855140. 3: Johnson RE, Ree H, Hartmann M, Lang L, Sawano S, Sarpong R. Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations. J Am Chem Soc. 2019 Feb 13;141(6):2233-2237. doi: 10.1021/jacs.8b13388. Epub 2019 Feb 4. PMID: 30702879; PMCID: PMC6742481. 4: Sahu S, Das B, Maji MS. Stereodivergent Total Synthesis of Hapalindoles, Fischerindoles, Hapalonamide H, and Ambiguine H Alkaloids by Developing a Biomimetic, Redox-Neutral, Cascade Prins-Type Cyclization. Org Lett. 2018 Oct 19;20(20):6485-6489. doi: 10.1021/acs.orglett.8b02804. Epub 2018 Oct 11. PMID: 30336678. 5: Zhu Q, Liu X. Discovery of a Calcium-Dependent Enzymatic Cascade for the Selective Assembly of Hapalindole-Type Alkaloids: On the Biosynthetic Origin of Hapalindole U. Angew Chem Int Ed Engl. 2017 Jul 24;56(31):9062-9066. doi: 10.1002/anie.201703932. Epub 2017 Jun 29. PMID: 28626997. 6: Swain SS, Paidesetty SK, Padhy RN. Antibacterial, antifungal and antimycobacterial compounds from cyanobacteria. Biomed Pharmacother. 2017 Jun;90:760-776. doi: 10.1016/j.biopha.2017.04.030. Epub 2017 Apr 15. PMID: 28419973. 7: Walton K, Berry JP. Indole Alkaloids of the Stigonematales (Cyanophyta): Chemical Diversity, Biosynthesis and Biological Activity. Mar Drugs. 2016 Apr 6;14(4):73. doi: 10.3390/md14040073. PMID: 27058546; PMCID: PMC4849077. 8: Hillwig ML, Zhu Q, Ittiamornkul K, Liu X. Discovery of a Promiscuous Non-Heme Iron Halogenase in Ambiguine Alkaloid Biogenesis: Implication for an Evolvable Enzyme Family for Late-Stage Halogenation of Aliphatic Carbons in Small Molecules. Angew Chem Int Ed Engl. 2016 May 4;55(19):5780-4. doi: 10.1002/anie.201601447. Epub 2016 Mar 30. PMID: 27027281. 9: Acuña UM, Zi J, Orjala J, Carcache de Blanco EJ. Ambiguine I Isonitrile from Fischerella ambigua Induces Caspase-Independent Cell Death in MCF-7 Hormone Dependent Breast Cancer Cells. Int J Cancer Res (Tortola). 2015 Mar;49(1):1655-1662. PMID: 26753095; PMCID: PMC4703120. 10: Liu X, Hillwig ML, Koharudin LM, Gronenborn AM. Unified biogenesis of ambiguine, fischerindole, hapalindole and welwitindolinone: identification of a monogeranylated indolenine as a cryptic common biosynthetic intermediate by an unusual magnesium-dependent aromatic prenyltransferase. Chem Commun (Camb). 2016 Jan 28;52(8):1737-40. doi: 10.1039/c5cc10060g. Epub 2016 Jan 7. PMID: 26740122; PMCID: PMC4720564. 11: Li S, Lowell AN, Yu F, Raveh A, Newmister SA, Bair N, Schaub JM, Williams RM, Sherman DH. Hapalindole/Ambiguine Biogenesis Is Mediated by a Cope Rearrangement, C-C Bond-Forming Cascade. J Am Chem Soc. 2015 Dec 16;137(49):15366-9. doi: 10.1021/jacs.5b10136. Epub 2015 Dec 2. PMID: 26629885; PMCID: PMC4681624. 12: Maimone TJ, Ishihara Y, Baran PS. Scalable Total Syntheses of (-)-Hapalindole U and (+)-Ambiguine H. Tetrahedron. 2015 May 2;71(22):3652-3665. doi: 10.1016/j.tet.2014.11.010. PMID: 25983347; PMCID: PMC4430130. 13: Walton K, Gantar M, Gibbs PD, Schmale MC, Berry JP. Indole alkaloids from Fischerella inhibit vertebrate development in the zebrafish (Danio rerio) embryo model. Toxins (Basel). 2014 Dec 22;6(12):3568-81. doi: 10.3390/toxins6123568. PMID: 25533520; PMCID: PMC4280548. 14: Micallef ML, Sharma D, Bunn BM, Gerwick L, Viswanathan R, Moffitt MC. Comparative analysis of hapalindole, ambiguine and welwitindolinone gene clusters and reconstitution of indole-isonitrile biosynthesis from cyanobacteria. BMC Microbiol. 2014 Aug 1;14:213. doi: 10.1186/s12866-014-0213-7. PMID: 25198896; PMCID: PMC4236562. 15: Hillwig ML, Fuhrman HA, Ittiamornkul K, Sevco TJ, Kwak DH, Liu X. Identification and characterization of a welwitindolinone alkaloid biosynthetic gene cluster in the stigonematalean Cyanobacterium Hapalosiphon welwitschii. Chembiochem. 2014 Mar 21;15(5):665-9. doi: 10.1002/cbic.201300794. PMID: 24677572; PMCID: PMC4382313. 16: Bhat V, Dave A, MacKay JA, Rawal VH. The Chemistry of Hapalindoles, Fischerindoles, Ambiguines, and Welwitindolinones. Alkaloids Chem Biol. 2014;73:65-160. doi: 10.1016/B978-0-12-411565-1.00002-0. Epub 2013 Dec 25. PMID: 26521649. 17: Hillwig ML, Zhu Q, Liu X. Biosynthesis of ambiguine indole alkaloids in cyanobacterium Fischerella ambigua. ACS Chem Biol. 2014 Feb 21;9(2):372-7. doi: 10.1021/cb400681n. Epub 2013 Nov 20. PMID: 24180436. 18: Rafferty RJ, Williams RM. FORMAL SYNTHESIS OF HAPALINDOLE O AND SYNTHETIC EFFORTS TOWARDS HAPALINDOLE K AND AMBIGUINE A. Heterocycles. 2012 May 1;86(1):219-231. doi: 10.3987/COM-12-S(N)3. PMID: 24808627; PMCID: PMC4010148. 19: Rafferty RJ, Williams RM. Synthetic Studies on the Ambiguine Family of Alkaloids: Construction of the ABCD Ring System. Tetrahedron Lett. 2011 Apr 27;52(17):2037-2040. doi: 10.1016/j.tetlet.2010.09.086. PMID: 21516192; PMCID: PMC3079252. 20: Mo S, Krunic A, Santarsiero BD, Franzblau SG, Orjala J. Hapalindole-related alkaloids from the cultured cyanobacterium Fischerella ambigua. Phytochemistry. 2010 Dec;71(17-18):2116-23. doi: 10.1016/j.phytochem.2010.09.004. Epub 2010 Oct 19. PMID: 20965528; PMCID: PMC2981615.