Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-04-29 00:31:52 UTC |
---|
Updated at | 2022-04-29 00:31:52 UTC |
---|
NP-MRD ID | NP0079511 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | Guanacone |
---|
Description | Guanacone belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. Guanacone is found in Annona aff. spraguei and Annona spraguei. It was first documented in 2005 (PMID: 16050134). Based on a literature review a small amount of articles have been published on guanacone (PMID: 33016836) (PMID: 17482824). |
---|
Structure | CCCCCCCCCC[C@H](O)[C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@H](O)CCCCC(=O)CCCCCCCC1=C[C@H](C)OC1=O InChI=1S/C37H64O7/c1-3-4-5-6-7-8-12-15-21-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)22-17-16-20-30(38)19-14-11-9-10-13-18-29-27-28(2)42-37(29)41/h27-28,31-36,39-40H,3-26H2,1-2H3/t28-,31-,32+,33+,34+,35+,36+/m0/s1 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C37H64O7 |
---|
Average Mass | 620.9120 Da |
---|
Monoisotopic Mass | 620.46520 Da |
---|
IUPAC Name | (5S)-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]-8-oxotridecyl]-5-methyl-2,5-dihydrofuran-2-one |
---|
Traditional Name | (5S)-3-[(13R)-13-hydroxy-13-[(2R,2'R,5R,5'R)-5'-[(1S)-1-hydroxyundecyl]-[2,2'-bioxolane]-5-yl]-8-oxotridecyl]-5-methyl-5H-furan-2-one |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCCCCCCCCC[C@H](O)[C@H]1CC[C@@H](O1)[C@H]1CC[C@@H](O1)[C@H](O)CCCCC(=O)CCCCCCCC1=C[C@H](C)OC1=O |
---|
InChI Identifier | InChI=1S/C37H64O7/c1-3-4-5-6-7-8-12-15-21-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)22-17-16-20-30(38)19-14-11-9-10-13-18-29-27-28(2)42-37(29)41/h27-28,31-36,39-40H,3-26H2,1-2H3/t28-,31-,32+,33+,34+,35+,36+/m0/s1 |
---|
InChI Key | WWBQKABSNQOYBU-YTUOZMILSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
---|
1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
---|
|
| Not Available | Species |
---|
Species of Origin | |
---|
Chemical Taxonomy |
---|
Description | Belongs to the class of organic compounds known as annonaceous acetogenins. These are waxy derivatives of fatty acids (usually C32 or C34), containing a terminal carboxylic acid combined with a 2-propanol unit at the C-2 position to form a methyl- substituted alpha,beta-unsaturated-gamma-lactone. One of their interesting structural features is a single, adjacent, or nonadjacent tetrahydrofuran (THF) or tetrahydropyran (THP) system with one or two flanking hydroxyl group(s) at the center of a long hydrocarbon chain. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Fatty Acyls |
---|
Sub Class | Fatty alcohols |
---|
Direct Parent | Annonaceous acetogenins |
---|
Alternative Parents | |
---|
Substituents | - Annonaceae acetogenin skeleton
- Long chain fatty alcohol
- 2-furanone
- Dihydrofuran
- Oxolane
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- Ketone
- Carboxylic acid ester
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Ether
- Dialkyl ether
- Organooxygen compound
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Organic oxygen compound
- Organic oxide
- Aliphatic heteromonocyclic compound
|
---|
Molecular Framework | Aliphatic heteromonocyclic compounds |
---|
External Descriptors | Not Available |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
General References | - Agu KC, Ayevbuomwan M, Imade RO, Okolie PN, Elekofehinti OO, Falodun A, Eluehike LN, Tasie MC, Ovie JJ, Obiajuru SK, Enakeno OR, Otsupius JA, Kashetu AI, Akeiti FO: Biochemical investigation of the upstream anti-sickling mechanisms of soursop (Annona muricata): 15-acetyl guanacone as an inhibitor of deoxyhaemoglobin polymerisation. J Biomol Struct Dyn. 2022 Mar;40(4):1503-1520. doi: 10.1080/07391102.2020.1828171. Epub 2020 Oct 5. [PubMed:33016836 ]
- Barrachina I, Royo I, Baldoni HA, Chahboune N, Suvire F, DePedro N, Zafra-Polo MC, Bermejo A, El Aouad N, Cabedo N, Saez J, Tormo JR, Enriz RD, Cortes D: New antitumoral acetogenin 'Guanacone type' derivatives: isolation and bioactivity. Molecular dynamics simulation of diacetyl-guanacone. Bioorg Med Chem. 2007 Jul 1;15(13):4369-81. doi: 10.1016/j.bmc.2007.04.039. Epub 2007 Apr 25. [PubMed:17482824 ]
- Tormo JR, DePedro N, Royo I, Barrachina I, Zafra-Polo MC, Cuadrillero C, Hernandez P, Cortes D, Pelaez F: In vitro antitumor structure-activity relationships of threo/trans/threo/trans/erythro bis-tetrahydrofuranic acetogenins: correlations with their inhibition of mitochondrial complex I. Oncol Res. 2005;15(3):129-38. doi: 10.3727/096504005776367915. [PubMed:16050134 ]
|
---|