| Record Information |
|---|
| Version | 2.0 |
|---|
| Created at | 2022-04-27 22:48:17 UTC |
|---|
| Updated at | 2022-04-27 22:48:17 UTC |
|---|
| NP-MRD ID | NP0051438 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | Chartreusin |
|---|
| Description | 3-{[(2S,3S,4S,5R,6S)-3-{[(2R,3R,4R,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]Icosa-1,3,5,7,9(19),12(20),13,15-octaene-10,17-dione belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. Chartreusin is found in Streptomyces chartreusis. Based on a literature review very few articles have been published on 3-{[(2S,3S,4S,5R,6S)-3-{[(2R,3R,4R,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.0²,⁷.0⁹,¹⁹.0¹⁶,²⁰]Icosa-1,3,5,7,9(19),12(20),13,15-octaene-10,17-dione. |
|---|
| Structure | CO[C@@H]1[C@@H](O)[C@@H](C)O[C@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](C)O[C@H]2OC2=C3C4=C5C(C(=O)OC6=CC=C(C)C(C(=O)O4)=C56)=C(O)C3=CC=C2)[C@@H]1O InChI=1S/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3/t11-,12+,21-,22-,24-,25+,27+,28-,31+,32-/m0/s1 |
|---|
| Synonyms | Not Available |
|---|
| Chemical Formula | C32H32O14 |
|---|
| Average Mass | 640.5940 Da |
|---|
| Monoisotopic Mass | 640.17921 Da |
|---|
| IUPAC Name | 3-{[(2S,3S,4S,5R,6S)-3-{[(2R,3R,4R,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(19),2,4,6,8,12,14,16(20)-octaene-10,17-dione |
|---|
| Traditional Name | 3-{[(2S,3S,4S,5R,6S)-3-{[(2R,3R,4R,5S,6R)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4,5-dihydroxy-6-methyloxan-2-yl]oxy}-8-hydroxy-15-methyl-11,18-dioxapentacyclo[10.6.2.0^{2,7}.0^{9,19}.0^{16,20}]icosa-1(19),2,4,6,8,12,14,16(20)-octaene-10,17-dione |
|---|
| CAS Registry Number | Not Available |
|---|
| SMILES | CO[C@@H]1[C@@H](O)[C@@H](C)O[C@H](O[C@H]2[C@@H](O)[C@@H](O)[C@H](C)O[C@H]2OC2=C3C4=C5C(C(=O)OC6=CC=C(C)C(C(=O)O4)=C56)=C(O)C3=CC=C2)[C@@H]1O |
|---|
| InChI Identifier | InChI=1S/C32H32O14/c1-10-8-9-15-18-16(10)29(38)45-26-17-13(23(35)20(19(18)26)30(39)43-15)6-5-7-14(17)44-32-28(24(36)21(33)11(2)42-32)46-31-25(37)27(40-4)22(34)12(3)41-31/h5-9,11-12,21-22,24-25,27-28,31-37H,1-4H3/t11-,12+,21-,22-,24-,25+,27+,28-,31+,32-/m0/s1 |
|---|
| InChI Key | PONPPNYZKHNPKZ-PGMJDTOWSA-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 naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Organoheterocyclic compounds |
|---|
| Class | Naphthopyrans |
|---|
| Sub Class | Naphthopyranones |
|---|
| Direct Parent | Naphthopyranone glycosides |
|---|
| Alternative Parents | |
|---|
| Substituents | - Naphthopyranone glycoside
- Phenolic glycoside
- O-glycosyl compound
- 1-naphthol
- Isocoumarin
- Glycosyl compound
- Disaccharide
- Coumarin
- 2-benzopyran
- 1-benzopyran
- Naphthalene
- Benzopyran
- Pyranone
- Benzenoid
- Pyran
- Oxane
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Lactone
- Oxacycle
- Ether
- Dialkyl ether
- Acetal
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Alcohol
- Aromatic heteropolycyclic compound
|
|---|
| Molecular Framework | Aromatic heteropolycyclic 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 | |
|---|