Basic information
- CAS
6377-18-0- Standard SMILES
CO[C@H]1[C@@H](O)[C@@H](C)O[C@H](O[C@H]2[C@H](Oc3cccc4c(O)c5c(=O)oc6ccc(C)c7c(=O)oc(c34)c5c67)O[C@H](C)[C@H](O)[C@@H]2O)[C@@H]1O- InChIKey
PONPPNYZKHNPKZ-RYBWXQSLSA-N- Molecular formula
- C32H32O14
- Average molar mass
- 640.6 g/mol
- Monoisotopic mass
- 640.1792057
Overview
Chartreusin is a glycoside and a benzochromenone.
Names & identifiers
- Preferred name
- Chartreusin
- IUPAC
- 3-[(2S,3R,4S,5R,6R)-3-[(2R,3R,4S,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(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dione
- English name
- CHARTREUSIN
- Molecular formula
- C32H32O14
- Molecular weight
- 640.59
Names & synonyms
Chartreusin6377-18-0Antibiotic X-465AHS0H395E3ODTXSID20930431Benzo(h)(1)benzopyrano(5,4,3-cde)(1)benzopyran-5,12-dione, 10-((6-deoxy-2-O-(6-deoxy-3-O-methyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl)oxy)-6-hydroxy-1-methyl-NSC-51593-[(2S,3R,4S,5R,6R)-3-[(2R,3R,4S,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(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dione3-((2S,3R,4S,5R,6R)-3-((2R,3R,4S,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(19),2(7),3,5,8,12(20),13,15-octaene-10,17-dioneRefChem:125068DTXCID901359158(1R,2R,3aS,8aR)-1-((Z)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl)-1-(hydroxymethyl)-2,5-dimethyl-2,3,4,7,8,8a-hexahydroazulene-3a-carbaldehyde
Show more names
nsc5159antibioticx-465a
Properties
Computed structural properties
- XLogP
- 2.1
- Topological polar surface area
- 200 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 14
- Rotatable bonds
- 5
- Heavy atoms
- 46
- Formal charge
- 0
- Complexity
- 1,150
Experimental & physicochemical properties
DrugsPharmaceuticals -> Antibiotics
LogP1.8
Physicochemical properties
- Melting point
- 185 ℃ · 185℃
- alpha
- 25 · D25 +132.5° (c = 0.2 in pyridine); D25 -33° (c = 0.3 in glacial acetic acid)
- Boiling point
- 592.39 °C · 592.39°C (rough estimate)
- Density
- 1.3027 · 1.3027 (rough estimate)
- refractive index
- 1.613 · 1.6130 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- Chloroform (Slightly, Heated), Methanol (Slightly), Pyridine (Slightly)
- form
- Yellow solid.
- pka
- 6 · 6+-.0.20(Predicted)
- color
- Light Yellow to Yellow
- Water Solubility
- 15 mg/L · 15mg/L(25 ºC)
Safety & regulation
GHS classification
GHS Classification
Warning
H351 (100%): Suspected of causing cancer [Warning Carcinogenicity]
P203, P280, P318, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 66 reports by companies from 2 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesCarc. 2 (100%)
Safety data
- hs_code
- 29419000
- risk_code
- 40
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- hazard_code
- Xn
- safety_code
- 22-36/37/39-45
- Hazard statements
- H351
- Precautionary statements
- P201-P202-P281-P308+P313-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationChemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Applications
UsesChartreusin is an antiproliferative agent that inhibits topoisomerase II.
UsesChartreusin is an antitumour antibiotic that binds to GC-rich tracts in DNA, with a clear preference for B-DNA over Z-DNA. It inhibits RNA synthesis and causes single-strand scission of DNA via the formation of free radicals. Chartreusin is also a potent inhibitor of topoisomerase II.
UsesChartreusin is an antitumor antibiotic that binds to GC-rich tracts in DNA, with a clear preference for B-DNA over Z-DNA. It inhibits RNA synthesis and causes single-strand scission of DNA via the formation of free radicals. Chartreusin is also a potent inhibitor of topoisomerase II.
Suppliers25 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
浙江珲达生物科技有限公司0571-89903022 18679456698 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
武汉凯威斯科技有限公司86-027-67849912 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
Related reactions
2 records
Compound notes
Loading…