Record Information |
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Version | 1.0 |
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Created at | 2022-09-06 18:48:01 UTC |
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Updated at | 2022-09-06 18:48:01 UTC |
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NP-MRD ID | NP0236007 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (s)-amino[(1s,7s,10r,11s,14r,23s,24r,26r,31r,32s,33r,34r,35s)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]acetic acid |
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Description | Pinnatoxin B belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. (s)-amino[(1s,7s,10r,11s,14r,23s,24r,26r,31r,32s,33r,34r,35s)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]acetic acid is found in Pinna muricata. It was first documented in 2006 (PMID: 16836397). Based on a literature review a significant number of articles have been published on Pinnatoxin B (PMID: 36088123) (PMID: 36088122) (PMID: 36088121) (PMID: 36088120) (PMID: 36088119) (PMID: 36088116). |
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Structure | C[C@H]1C[C@]23CC4CCC[C@]5(CC[C@]6(O5)O[C@H](CC[C@]6(C)O)CC(=C)CCCC5=NC[C@@H](C)[C@H](C)C[C@@]55CCC(=C[C@H]5[C@H](O2)[C@H](O3)[C@@H]1O)[C@H](N)C(O)=O)O4 InChI=1S/C42H64N2O9/c1-24-8-6-10-32-39(20-25(2)27(4)23-44-32)15-11-28(33(43)37(46)47)19-31(39)35-36-34(45)26(3)21-41(51-35,52-36)22-30-9-7-13-40(49-30)16-17-42(53-40)38(5,48)14-12-29(18-24)50-42/h19,25-27,29-31,33-36,45,48H,1,6-18,20-23,43H2,2-5H3,(H,46,47)/t25-,26+,27-,29-,30?,31+,33+,34-,35+,36-,38+,39-,40+,41+,42-/m1/s1 |
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Synonyms | Value | Source |
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Pinnatoxin C | MeSH |
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Chemical Formula | C42H64N2O9 |
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Average Mass | 740.9790 Da |
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Monoisotopic Mass | 740.46118 Da |
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IUPAC Name | Not Available |
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Traditional Name | Not Available |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]1C[C@]23CC4CCC[C@]5(CC[C@]6(O5)O[C@H](CC[C@]6(C)O)CC(=C)CCCC5=NC[C@@H](C)[C@H](C)C[C@@]55CCC(=C[C@H]5[C@H](O2)[C@H](O3)[C@@H]1O)[C@H](N)C(O)=O)O4 |
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InChI Identifier | InChI=1S/C42H64N2O9/c1-24-8-6-10-32-39(20-25(2)27(4)23-44-32)15-11-28(33(43)37(46)47)19-31(39)35-36-34(45)26(3)21-41(51-35,52-36)22-30-9-7-13-40(49-30)16-17-42(53-40)38(5,48)14-12-29(18-24)50-42/h19,25-27,29-31,33-36,45,48H,1,6-18,20-23,43H2,2-5H3,(H,46,47)/t25-,26+,27-,29-,30?,31+,33+,34-,35+,36-,38+,39-,40+,41+,42-/m1/s1 |
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InChI Key | HSMXADLEHIWNJP-NVUAXAQASA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | L-alpha-amino acids |
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Alternative Parents | |
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Substituents | - L-alpha-amino acid
- Azepine
- Ketal
- Oxepane
- Oxane
- Meta-dioxolane
- Oxolane
- Tertiary alcohol
- Ketimine
- Amino acid
- Secondary alcohol
- Acetal
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Propargyl-type 1,3-dipolar organic compound
- Organic 1,3-dipolar compound
- Organooxygen compound
- Organonitrogen compound
- Alcohol
- Primary aliphatic amine
- Organopnictogen compound
- Imine
- Organic oxide
- Hydrocarbon derivative
- Primary amine
- Amine
- Organic oxygen compound
- Carbonyl group
- Organic nitrogen compound
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic heteropolycyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Xu X, Rothrock MJ Jr, Reeves J, Kumar GD, Mishra A: Using E. coli population to predict foodborne pathogens in pastured poultry farms. Food Microbiol. 2022 Dec;108:104092. doi: 10.1016/j.fm.2022.104092. Epub 2022 Jul 14. [PubMed:36088123 ]
- Lanzl MI, Zwietering MH, Abee T, den Besten HMW: Combining enrichment with multiplex real-time PCR leads to faster detection and identification of Campylobacter spp. in food compared to ISO 10272-1:2017. Food Microbiol. 2022 Dec;108:104117. doi: 10.1016/j.fm.2022.104117. Epub 2022 Aug 19. [PubMed:36088122 ]
- Cacciatore FA, Maders C, Alexandre B, Barreto Pinilla CM, Brandelli A, da Silva Malheiros P: Carvacrol encapsulation into nanoparticles produced from chia and flaxseed mucilage: Characterization, stability and antimicrobial activity against Salmonella and Listeria monocytogenes. Food Microbiol. 2022 Dec;108:104116. doi: 10.1016/j.fm.2022.104116. Epub 2022 Aug 18. [PubMed:36088121 ]
- Liu X, Li Y, Micallef SA: Developmentally related and drought-induced shifts in the kale metabolome limited Salmonella enterica association, providing novel insights to enhance food safety. Food Microbiol. 2022 Dec;108:104113. doi: 10.1016/j.fm.2022.104113. Epub 2022 Aug 18. [PubMed:36088120 ]
- Dos Santos AMP, Panzenhagen P, Ferrari RG, Conte-Junior CA: Large-scale genomic analysis reveals the pESI-like megaplasmid presence in Salmonella Agona, Muenchen, Schwarzengrund, and Senftenberg. Food Microbiol. 2022 Dec;108:104112. doi: 10.1016/j.fm.2022.104112. Epub 2022 Aug 12. [PubMed:36088119 ]
- Centeno JA, Lorenzo JM, Carballo J: Effects of autochthonous Kluyveromyces lactis and commercial Enterococcus faecium adjunct cultures on the volatile profile and the sensory characteristics of short-ripened acid-curd Cebreiro cheese. Food Microbiol. 2022 Dec;108:104101. doi: 10.1016/j.fm.2022.104101. Epub 2022 Aug 1. [PubMed:36088116 ]
- Liu MK, Liu CY, Tian XH, Feng J, Guo XJ, Liu Y, Zhang XY, Tang YM: Bioremediation of degraded pit mud by indigenous microbes for Baijiu production. Food Microbiol. 2022 Dec;108:104096. doi: 10.1016/j.fm.2022.104096. Epub 2022 Aug 4. [PubMed:36088112 ]
- Chen J, Yang R, Wang Y, Koseki S, Fu L, Wang Y: Inhibitory effect of d-Tryptophan on the spoilage potential of Shewanella baltica and Pseudomonas fluorescens and its potential application in salmon fillet preservation. Food Microbiol. 2022 Dec;108:104104. doi: 10.1016/j.fm.2022.104104. Epub 2022 Aug 9. [PubMed:36088118 ]
- Wicaksono WA, Buko A, Kusstatscher P, Sinkkonen A, Laitinen OH, Virtanen SM, Hyoty H, Cernava T, Berg G: Modulation of the food microbiome by apple fruit processing. Food Microbiol. 2022 Dec;108:104103. doi: 10.1016/j.fm.2022.104103. Epub 2022 Aug 4. [PubMed:36088117 ]
- Jyung S, Kang JW, Kang DH: L. monocytogens exhibited less cell membrane damage, lipid peroxidation, and intracellular reactive oxygen species accumulation after plasma-activated water treatment compared to E. coli O157:H7 and S. Typhimurium. Food Microbiol. 2022 Dec;108:104098. doi: 10.1016/j.fm.2022.104098. Epub 2022 Jul 30. [PubMed:36088114 ]
- Parafati L, Restuccia C, Cirvilleri G: Efficacy and mechanism of action of food isolated yeasts in the control of Aspergillus flavus growth on pistachio nuts. Food Microbiol. 2022 Dec;108:104100. doi: 10.1016/j.fm.2022.104100. Epub 2022 Aug 6. [PubMed:36088115 ]
- Tofalo R, Perpetuini G, Rossetti AP, Gaggiotti S, Piva A, Olivastri L, Cichelli A, Compagnone D, Arfelli G: Impact of Saccharomyces cerevisiae and non-Saccharomyces yeasts to improve traditional sparkling wines production. Food Microbiol. 2022 Dec;108:104097. doi: 10.1016/j.fm.2022.104097. Epub 2022 Jul 20. [PubMed:36088113 ]
- Fu Z, Piumsomboon A, Punnarak P, Uttayarnmanee P, Leaw CP, Lim PT, Wang A, Gu H: Diversity and distribution of harmful microalgae in the Gulf of Thailand assessed by DNA metabarcoding. Harmful Algae. 2021 Jun;106:102063. doi: 10.1016/j.hal.2021.102063. Epub 2021 Jun 11. [PubMed:34154784 ]
- Lu CD, Zakarian A: Studies toward the synthesis of pinnatoxins: the B,C,D-dispiroketal fragment. Org Lett. 2007 Aug 2;9(16):3161-3. doi: 10.1021/ol071266e. Epub 2007 Jul 12. [PubMed:17628070 ]
- Matsuura F, Hao J, Reents R, Kishi Y: Total synthesis and stereochemistry of pinnatoxins B and C. Org Lett. 2006 Jul 20;8(15):3327-30. doi: 10.1021/ol0611548. [PubMed:16836397 ]
- LOTUS database [Link]
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