| Record Information |
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| Version | 2.0 |
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| Created at | 2022-05-11 16:53:51 UTC |
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| Updated at | 2022-05-11 16:53:51 UTC |
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| NP-MRD ID | NP0087590 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Lacto-N-fucoheptaose |
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| Description | Lacto-N-fucoheptaose belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. Milk oligosaccharides vary among individuals and over the course of lactation. In human milk, both free and bound oligosaccharides have potential biological activity and are known to inhibit viral infection. Lacto-N-fucoheptaose is a heptasaccharide found in human breast milk. Lacto-N-fucoheptaose was first documented in 1975 (PMID: 1132510). Lacto-N-fucoheptaose is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 10744332). |
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| Structure | CC1OC(OC2(CC(NC(C)=O)C(OC3C(O)C(COC4OC(CO)C(OC5OC(CO)C(O)C(O)C5O)C(O)C4NC(C)=O)OC(OC(C(O)CO)C(O)C(O)C=O)C3O)OC2CO)OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O InChI=1S/C46H78N2O35/c1-12-24(59)30(65)34(69)44(73-12)82-46(83-45-35(70)32(67)27(62)19(8-52)75-45)4-15(47-13(2)55)40(78-22(46)10-54)81-39-28(63)21(77-43(36(39)71)79-37(17(58)6-50)25(60)16(57)5-49)11-72-41-23(48-14(3)56)29(64)38(20(9-53)76-41)80-42-33(68)31(66)26(61)18(7-51)74-42/h5,12,15-45,50-54,57-71H,4,6-11H2,1-3H3,(H,47,55)(H,48,56) |
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| Synonyms | | Value | Source |
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| O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-[O-beta-D-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)]-O-beta-D-galactopyranosyl-(1->4)- D-glucose | HMDB | | O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-[O-beta-delta-galactopyranosyl-(1->4)-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->6)]-O-beta-delta-galactopyranosyl-(1->4)- D-glucose | HMDB | | N-[2-({3,5-dihydroxy-2-[({4-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl}oxy)methyl]-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl}oxy)-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl]ethanimidate | HMDB | | Lacto-N-fucoheptaose | MeSH |
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| Chemical Formula | C46H78N2O35 |
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| Average Mass | 1219.1039 Da |
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| Monoisotopic Mass | 1218.43851 Da |
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| IUPAC Name | N-(2-{[2-({[3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl)acetamide |
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| Traditional Name | N-(2-{[2-({[3-acetamido-4-hydroxy-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}methyl)-3,5-dihydroxy-6-[(1,2,4,5-tetrahydroxy-6-oxohexan-3-yl)oxy]oxan-4-yl]oxy}-6-(hydroxymethyl)-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl)acetamide |
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| CAS Registry Number | Not Available |
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| SMILES | CC1OC(OC2(CC(NC(C)=O)C(OC3C(O)C(COC4OC(CO)C(OC5OC(CO)C(O)C(O)C5O)C(O)C4NC(C)=O)OC(OC(C(O)CO)C(O)C(O)C=O)C3O)OC2CO)OC2OC(CO)C(O)C(O)C2O)C(O)C(O)C1O |
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| InChI Identifier | InChI=1S/C46H78N2O35/c1-12-24(59)30(65)34(69)44(73-12)82-46(83-45-35(70)32(67)27(62)19(8-52)75-45)4-15(47-13(2)55)40(78-22(46)10-54)81-39-28(63)21(77-43(36(39)71)79-37(17(58)6-50)25(60)16(57)5-49)11-72-41-23(48-14(3)56)29(64)38(20(9-53)76-41)80-42-33(68)31(66)26(61)18(7-51)74-42/h5,12,15-45,50-54,57-71H,4,6-11H2,1-3H3,(H,47,55)(H,48,56) |
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| InChI Key | DUUXDOCGEHMZIH-UHFFFAOYSA-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, 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 |
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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 oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. |
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| Kingdom | Organic compounds |
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| Super Class | Organic oxygen compounds |
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| Class | Organooxygen compounds |
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| Sub Class | Carbohydrates and carbohydrate conjugates |
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| Direct Parent | Oligosaccharides |
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| Alternative Parents | |
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| Substituents | - Oligosaccharide
- Fatty acyl glycoside
- N-acyl-alpha-hexosamine
- Alkyl glycoside
- Glycosyl compound
- O-glycosyl compound
- Ketal
- Beta-hydroxy aldehyde
- Oxane
- Fatty acyl
- Alpha-hydroxyaldehyde
- Acetamide
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Organoheterocyclic compound
- Polyol
- Acetal
- Oxacycle
- Carboxylic acid derivative
- Aldehyde
- Organopnictogen compound
- Organic oxide
- Hydrocarbon derivative
- Carbonyl group
- Organonitrogen compound
- Organic nitrogen compound
- Alcohol
- Primary alcohol
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic 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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