Andrimid

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

MedKoo CAT#: 535073

CAS#: 108868-95-7

Description: Andrimid, also known as UFC-N 11, is a peptide antibiotic; an anti-Bacillus compound in the marine sponge, Hyatella sp. It was found that the antibacterial compound andrimid from V. coralliilyticus induces transcription of biosynthetic gene clusters and increases production of antibiotic holomycin in P. galatheae.

Chemical Structure

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Andrimid
CAS# 108868-95-7
Instruction

Theoretical Analysis

MedKoo Cat#: 535073
Name: Andrimid
CAS#: 108868-95-7
Chemical Formula: C27H33N3O5
Exact Mass: 479.24
Molecular Weight: 479.577
Elemental Analysis: C, 67.62; H, 6.94; N, 8.76; O, 16.68

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Andrimid; UFC-N 11; UFC-N11; UFC-N-11;

IUPAC/Chemical Name: Benzenepropanamide, N-(2-methyl-1-((4-methyl-2,5-dioxo-3-pyrrolidinyl)carbonyl)propyl)-beta-((1-oxo-2,4,6-octatrienyl)amino)-, (3S-(3alpha(R*(R*(2E,4E,6E))),4beta))-

InChi Key: OHDXGZAYYBMHCY-QSUIEZAASA-N

InChi Code: InChI=1S/C27H33N3O5/c1-5-6-7-8-12-15-21(31)28-20(19-13-10-9-11-14-19)16-22(32)29-24(17(2)3)25(33)23-18(4)26(34)30-27(23)35/h5-15,17-18,20,23-24H,16H2,1-4H3,(H,28,31)(H,29,32)(H,30,34,35)/b6-5+,8-7+,15-12+/t18-,20-,23+,24-/m0/s1

SMILES Code: O=C(N[C@H](C([C@@H]([C@@H]1C)C(NC1=O)=O)=O)C(C)C)C[C@H](NC(/C=C/C=C/C=C/C)=O)C2=CC=CC=C2

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 479.58 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Cheng T, Ge T, Zhao L, Hou Y, Xia J, Zhao L. Improved production of andrimid in Erwinia persicina BST187 strain by fermentation optimization. BMC Microbiol. 2023 Sep 25;23(1):268. doi: 10.1186/s12866-023-02946-2. PMID: 37749510; PMCID: PMC10519088.


2: Zhao L, Ge T, Cheng T, Wang Q, Cui M, Yuan H, Zhao L. Fine-tuning gene expression of regulator AdmX for improved biosynthesis of andrimid in Erwinia persicina BST187. Appl Microbiol Biotechnol. 2023 Nov;107(22):6775-6788. doi: 10.1007/s00253-023-12770-3. Epub 2023 Sep 16. PMID: 37715803.


3: Toor HG, Banerjee DI, Chauhan JB. In Silico Evaluation of Human Cathelicidin LL-37 as a Novel Therapeutic Inhibitor of Panton-Valentine Leukocidin Toxin of Methicillin-Resistant Staphylococcus aureus. Microb Drug Resist. 2021 May;27(5):602-615. doi: 10.1089/mdr.2020.0196. Epub 2020 Oct 13. PMID: 33983855.


4: Buijs Y, Zhang SD, Jørgensen KM, Isbrandt T, Larsen TO, Gram L. Enhancement of antibiotic production by co-cultivation of two antibiotic producing marine Vibrionaceae strains. FEMS Microbiol Ecol. 2021 Mar 31;97(4):fiab041. doi: 10.1093/femsec/fiab041. PMID: 33693627.


5: Messiha HL, Payne KAP, Scrutton NS, Leys D. A Biological Route to Conjugated Alkenes: Microbial Production of Hepta-1,3,5-triene. ACS Synth Biol. 2021 Feb 19;10(2):228-235. doi: 10.1021/acssynbio.0c00464. Epub 2021 Feb 3. PMID: 33535752.


6: Buijs Y, Isbrandt T, Zhang SD, Larsen TO, Gram L. The Antibiotic Andrimid Produced by Vibrio coralliilyticus Increases Expression of Biosynthetic Gene Clusters and Antibiotic Production in Photobacterium galatheae. Front Microbiol. 2020 Dec 22;11:622055. doi: 10.3389/fmicb.2020.622055. PMID: 33424823; PMCID: PMC7793655.


7: Matilla MA, Daddaoua A, Chini A, Morel B, Krell T. An auxin controls bacterial antibiotics production. Nucleic Acids Res. 2018 Nov 30;46(21):11229-11238. doi: 10.1093/nar/gky766. PMID: 30500953; PMCID: PMC6265452.


8: Wu Y, Seyedsayamdost MR. The Polyene Natural Product Thailandamide A Inhibits Fatty Acid Biosynthesis in Gram-Positive and Gram-Negative Bacteria. Biochemistry. 2018 Jul 24;57(29):4247-4251. doi: 10.1021/acs.biochem.8b00678. Epub 2018 Jul 12. PMID: 29975047.


9: Matilla MA, Udaondo Z, Krell T, Salmond GP. Genome Sequence of Serratia marcescens MSU97, a Plant-Associated Bacterium That Makes Multiple Antibiotics. Genome Announc. 2017 Mar 2;5(9):e01752-16. doi: 10.1128/genomeA.01752-16. PMID: 28254993; PMCID: PMC5334600.


10: Giubergia S, Phippen C, Nielsen KF, Gram L. Growth on Chitin Impacts the Transcriptome and Metabolite Profiles of Antibiotic-Producing Vibrio coralliilyticus S2052 and Photobacterium galatheae S2753. mSystems. 2017 Jan 3;2(1):e00141-16. doi: 10.1128/mSystems.00141-16. PMID: 28066819; PMCID: PMC5209532.


11: Ishikawa F, Sugimoto H, Kakeya H. In Vitro Investigation of Crosstalk between Fatty Acid and Polyketide Synthases in the Andrimid Biosynthetic Assembly Line. Chembiochem. 2016 Nov 17;17(22):2137-2142. doi: 10.1002/cbic.201600410. Epub 2016 Oct 11. PMID: 27598417.


12: Mamo G. Anaerobes as Sources of Bioactive Compounds and Health Promoting Tools. Adv Biochem Eng Biotechnol. 2016;156:433-464. doi: 10.1007/10_2016_6. PMID: 27432247.


13: Dutkiewicz J, Mackiewicz B, Lemieszek MK, Golec M, Milanowski J. Pantoea agglomerans: a mysterious bacterium of evil and good. Part IV. Beneficial effects. Ann Agric Environ Med. 2016 Jun 2;23(2):206-22. doi: 10.5604/12321966.1203879. PMID: 27294621.


14: Matilla MA, Drew A, Udaondo Z, Krell T, Salmond GP. Genome Sequence of Serratia plymuthica A153, a Model Rhizobacterium for the Investigation of the Synthesis and Regulation of Haterumalides, Zeamine, and Andrimid. Genome Announc. 2016 May 19;4(3):e00373-16. doi: 10.1128/genomeA.00373-16. PMID: 27198016; PMCID: PMC4888998.


15: Matilla MA, Nogellova V, Morel B, Krell T, Salmond GP. Biosynthesis of the acetyl-CoA carboxylase-inhibiting antibiotic, andrimid in Serratia is regulated by Hfq and the LysR-type transcriptional regulator, AdmX. Environ Microbiol. 2016 Nov;18(11):3635-3650. doi: 10.1111/1462-2920.13241. Epub 2016 May 25. PMID: 26914969; PMCID: PMC5216899.


16: Neu AK, Månsson M, Gram L, Prol-García MJ. Toxicity of bioactive and probiotic marine bacteria and their secondary metabolites in Artemia sp. and Caenorhabditis elegans as eukaryotic model organisms. Appl Environ Microbiol. 2014 Jan;80(1):146-53. doi: 10.1128/AEM.02717-13. Epub 2013 Oct 18. PMID: 24141121; PMCID: PMC3911035.


17: Sánchez LA, Sierra MG, Siñeriz F, Delgado O. Andrimid production at low temperature by a psychrotolerant Serratia proteamaculans strain. World J Microbiol Biotechnol. 2013 Oct;29(10):1773-81. doi: 10.1007/s11274-013-1338-9. Epub 2013 Apr 5. PMID: 23558460.


18: Bryant SK, Waldrop GL, Gilman SD. A capillary electrophoretic assay for acetyl coenzyme A carboxylase. Anal Biochem. 2013 Jun 1;437(1):32-8. doi: 10.1016/j.ab.2013.02.005. Epub 2013 Feb 19. PMID: 23435309; PMCID: PMC3627828.


19: Graff JR, Forschner-Dancause SR, Menden-Deuer S, Long RA, Rowley DC. Vibrio cholerae Exploits Sub-Lethal Concentrations of a Competitor-Produced Antibiotic to Avoid Toxic Interactions. Front Microbiol. 2013 Jan 31;4:8. doi: 10.3389/fmicb.2013.00008. PMID: 23386845; PMCID: PMC3559943.


20: Zhu JL, Li DB, Yu XP. [Cloning and function identification of gene 'admA' and up-stream regulatory sequence related to antagonistic activity of Enterobacter cloacae B8]. Yi Chuan. 2012 Apr;34(4):495-502. Chinese. doi: 10.3724/sp.j.1005.2012.00495. PMID: 22522167.