Record Information |
---|
Version | 1.0 |
---|
Created at | 2022-09-09 00:35:17 UTC |
---|
Updated at | 2022-09-09 00:35:17 UTC |
---|
NP-MRD ID | NP0276452 |
---|
Secondary Accession Numbers | None |
---|
Natural Product Identification |
---|
Common Name | 3-{10,13-dihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5-methyl-5h-furan-2-one |
---|
Description | Squamocin F 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. Squamocin F is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Squamocin F has been detected, but not quantified in, fruits. 3-{10,13-dihydroxy-13-[5'-(1-hydroxyundecyl)-[2,2'-bioxolan]-5-yl]tridecyl}-5-methyl-5h-furan-2-one is found in Annona squamosa. It was first documented in 2000 (PMID: 11413487). This could make squamocin F a potential biomarker for the consumption of these foods (PMID: 16902246) (PMID: 17374880) (PMID: 20044567). |
---|
Structure | CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCC(O)CCCCCCCCCC1=CC(C)OC1=O InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)22-21-30(38)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3 |
---|
Synonyms | Not Available |
---|
Chemical Formula | C37H66O7 |
---|
Average Mass | 622.9157 Da |
---|
Monoisotopic Mass | 622.48085 Da |
---|
IUPAC Name | 3-(10,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-2,5-dihydrofuran-2-one |
---|
Traditional Name | 3-(10,13-dihydroxy-13-{5-[5-(1-hydroxyundecyl)oxolan-2-yl]oxolan-2-yl}tridecyl)-5-methyl-5H-furan-2-one |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCCCCCCCCCC(O)C1CCC(O1)C1CCC(O1)C(O)CCC(O)CCCCCCCCCC1=CC(C)OC1=O |
---|
InChI Identifier | InChI=1S/C37H66O7/c1-3-4-5-6-7-11-14-17-20-31(39)33-23-25-35(43-33)36-26-24-34(44-36)32(40)22-21-30(38)19-16-13-10-8-9-12-15-18-29-27-28(2)42-37(29)41/h27-28,30-36,38-40H,3-26H2,1-2H3 |
---|
InChI Key | OMAAXGPFIAQGDB-UHFFFAOYSA-N |
---|
Experimental Spectra |
---|
|
| Not Available | Predicted Spectra |
---|
|
| Not Available | 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
- Tetrahydrofuran
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Secondary alcohol
- Lactone
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Ether
- Dialkyl ether
- Carboxylic acid derivative
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Hydrocarbon derivative
- Alcohol
- 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 | |
---|