| Record Information |
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| Version | 2.0 |
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| Created at | 2024-12-06 20:59:19 UTC |
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| Updated at | 2025-10-21 03:41:06 UTC |
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| NP-MRD ID | NP0342304 |
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| Natural Product DOI | https://doi.org/10.57994/4240 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Trichogin A IV |
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| Description | Trichogin A IV belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. Trichogin A IV was first documented in 1994 (PMID: 7773780). Based on a literature review a small amount of articles have been published on Trichogin A IV (PMID: 8924625) (PMID: 7696554) (PMID: 8011270). |
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| Structure | CCCCCCCC(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CO)CC(C)C InChI=1S/C52H95N11O12/c1-16-18-19-20-21-22-38(65)61-50(10,11)47(73)55-28-41(68)59-37(25-33(7)8)45(71)62-51(12,13)48(74)54-26-39(66)53-27-40(67)58-36(24-32(5)6)44(70)63-52(14,15)49(75)56-29-42(69)60-43(34(9)17-2)46(72)57-35(30-64)23-31(3)4/h31-37,43,64H,16-30H2,1-15H3,(H,53,66)(H,54,74)(H,55,73)(H,56,75)(H,57,72)(H,58,67)(H,59,68)(H,60,69)(H,61,65)(H,62,71)(H,63,70)/t34-,35-,36-,37-,43-/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C52H95N11O12 |
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| Average Mass | 1066.3970 Da |
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| Monoisotopic Mass | 1065.71617 Da |
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| IUPAC Name | N-{1-[({[(1S)-1-{[1-({[({[(1S)-1-({1-[({[(1S,2S)-1-{[(2S)-1-hydroxy-4-methylpentan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]-1-methylethyl}carbamoyl)-3-methylbutyl]carbamoyl}methyl)carbamoyl]methyl}carbamoyl)-1-methylethyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-1-methylethyl}octanamide |
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| Traditional Name | N-{1-[({[(1S)-1-{[1-({[({[(1S)-1-({1-[({[(1S,2S)-1-{[(2S)-1-hydroxy-4-methylpentan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}methyl)carbamoyl]-1-methylethyl}carbamoyl)-3-methylbutyl]carbamoyl}methyl)carbamoyl]methyl}carbamoyl)-1-methylethyl]carbamoyl}-3-methylbutyl]carbamoyl}methyl)carbamoyl]-1-methylethyl}octanamide |
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| CAS Registry Number | Not Available |
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| SMILES | CCCCCCCC(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)NC(C)(C)C(=O)NCC(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](CO)CC(C)C |
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| InChI Identifier | InChI=1S/C52H95N11O12/c1-16-18-19-20-21-22-38(65)61-50(10,11)47(73)55-28-41(68)59-37(25-33(7)8)45(71)62-51(12,13)48(74)54-26-39(66)53-27-40(67)58-36(24-32(5)6)44(70)63-52(14,15)49(75)56-29-42(69)60-43(34(9)17-2)46(72)57-35(30-64)23-31(3)4/h31-37,43,64H,16-30H2,1-15H3,(H,53,66)(H,54,74)(H,55,73)(H,56,75)(H,57,72)(H,58,67)(H,59,68)(H,60,69)(H,61,65)(H,62,71)(H,63,70)/t34-,35-,36-,37-,43-/m0/s1 |
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| InChI Key | LZAAXJCEERCDPT-CKFFZNTQSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| 1D NMR | 13C NMR Spectrum (1D, 151 MHz, C2D6OS, experimental) | Not Available | Not Available | Marcelo | 2025-06-30 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental) | Not Available | Not Available | Marcelo | 2025-06-30 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C2D6OS, experimental) | Not Available | Not Available | Marcelo | 2025-06-30 | View Spectrum |
| | Predicted Spectra |
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| | Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Trichoderma sp. L2-2 | | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues. |
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| Kingdom | Organic compounds |
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| Super Class | Organic Polymers |
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| Class | Polypeptides |
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| Sub Class | Not Available |
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| Direct Parent | Polypeptides |
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| Alternative Parents | |
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| Substituents | - Polypeptide
- Alpha peptide
- Leucine or derivatives
- Isoleucine or derivatives
- N-acyl-alpha amino acid or derivatives
- Alpha-amino acid amide
- N-substituted-alpha-amino acid
- Alpha-amino acid or derivatives
- Fatty acyl
- Fatty amide
- N-acyl-amine
- Carboxamide group
- Secondary carboxylic acid amide
- Carboxylic acid derivative
- Alcohol
- Organonitrogen compound
- Organooxygen compound
- Primary alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Organic oxygen compound
- Organic nitrogen compound
- Aliphatic acyclic compound
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| Molecular Framework | Aliphatic acyclic 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 | - Monaco V, Formaggio F, Crisma M, Toniolo C, Shui X, Eggleston DS: Crystallographic structure of a multiple beta-turn containing, glycine-rich heptapeptide: a synthetic precursor of the lipopeptaibol antibiotic trichodecenin I. Biopolymers. 1996 Jul;39(1):31-42. doi: 10.1002/(SICI)1097-0282(199607)39:1%3C31::AID-BIP4%3E3.0.CO;2-W. [PubMed:8924625 ]
- Gurunath R, Balaram P: A nonhelical, multiple beta-turn conformation in a glycine-rich heptapeptide fragment of trichogin A IV containing a single central alpha-aminoisobutyric acid residue. Biopolymers. 1995 Jan;35(1):21-9. doi: 10.1002/bip.360350104. [PubMed:7696554 ]
- Toniolo C, Peggion C, Crisma M, Formaggio F, Shui X, Eggleston DS: Structure determination of racemic trichogin A IV using centrosymmetric crystals. Nat Struct Biol. 1994 Dec;1(12):908-14. doi: 10.1038/nsb1294-908. [PubMed:7773780 ]
- Crisma M, Valle G, Monaco V, Formaggio F, Toniolo C: N alpha-benzyloxycarbonyl-alpha-aminoisobutyryl-glycyl-L-isoleucyl- L-leucine methyl ester monohydrate. Acta Crystallogr C. 1994 Apr 15;50 ( Pt 4):563-5. doi: 10.1107/s0108270193010595. [PubMed:8011270 ]
- DOI: 10.1021/acsomega.5c05271
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