Basic information
- CAS
77879-89-1- Standard SMILES
COc1cc2c(oc(=O)c3cc(C)cc(OC)c32)c2c([C@H]3O[C@H](C)[C@H](O)[C@H](O)[C@H]3O)ccc(O)c12- InChIKey
LAFIWGHCXCBAPO-CGVLGGEFSA-N- Molecular formula
- C26H26O9
- Average molar mass
- 482.5 g/mol
- Monoisotopic mass
- 482.1576824
Overview
1-hydroxy-10,12-dimethoxy-8-methyl-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]naphtho[1,2-c]isochromen-6-one has been reported in Streptomyces, Streptomyces griseoflavus, and other organisms with data available.
Names & identifiers
- Preferred name
- 1,5-Anhydro-6-deoxy-1-(1-hydroxy-10,12-dimethoxy-8-methyl-6-oxo-6H-benzo(d)naphtho(1,2-b)pyran-4-yl)hexitol
- IUPAC
- 1-hydroxy-10,12-dimethoxy-8-methyl-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]naphtho[1,2-c]isochromen-6-one
- English name
- 6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 4-(6-deoxy-alpha-galactofuranosy l)-1-hydroxy-10,12-dimethoxy-8-methyl-
- Molecular formula
- C26H26O9
- Molecular weight
- 482.48
Names & synonyms
DTXSID209990681,5-Anhydro-6-deoxy-1-(1-hydroxy-10,12-dimethoxy-8-methyl-6-oxo-6H-benzo(d)naphtho(1,2-b)pyran-4-yl)hexitol1,5-Anhydro-6-deoxy-1-(1-hydroxy-10,12-dimethoxy-8-methyl-6-oxo-6H-benzo[d]naphtho[1,2-b]pyran-4-yl)hexitolRefChem:1053408DTXCID101426044DC-38-MBRN 5675008SCHEMBL298843641-hydroxy-10,12-dimethoxy-8-methyl-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]naphtho[1,2-c]isochromen-6-oneDB-216124(1R)-1,5-Anhydro-6-deoxy-1-(1-hydroxy-10,12-dimethoxy-8-methyl-6-oxo-6H-benzo[d]naphtho[1,2-b]pyran-4-yl)-D-galactitolgilvocarcin M
Show more names
AnandiMycin B, ToroMycin B, 1072A4-(6-Deoxy-α-L-galactofuranosyl)-1-hydroxy-10,12-dimethoxy-8-methyl-6H-benzo[d]naphtho[1,2-b]pyran-6-one6H-Benzo[d]naphtho[1,2-b]pyran-6-one, 4-(6-deoxy-α-D-galactofuranosyl)-1-hydroxy-10,12-dimethoxy-8-methyl-6H-Benzo(d)naphtho(1,2-b)pyran-6-one, 4-(6-deoxy-alpha-galactofuranosy l)-1-hydroxy-10,12-dimethoxy-8-methyl-
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 3
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 778
Physicochemical properties
- Boiling point
- 807.966 · 807.966±65.00 °C(Press: 760.00 Torr)(predicted)
- Density
- 1.453 · 1.453±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
- storage temp.
- -20 °C · Store at -20°C
- solubility
- DMF: soluble; DMSO: soluble
- form
- Yellow solid.
- pka
- 8.595 · 8.595±0.20(predicted)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302+H312+H332
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P321-P330-P362+P364-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302+H312+H332
- Precautionary statements
- P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P321-P330-P362+P364-P501
Chemistry & industry
Applications
DescriptionGilvocarcin M is an antibiotic originally isolated from S. gilvotanareus. It is active against S. aureus when used at a concentration of 32 μg/ml. Gilvocarcin M inhibits growth of KB cells (IC50 = 0.52 μg/ml) but has no effect on survival in a P388 mouse model of leukemia when used at doses ranging from 25 to 400 mg/kg. Gilvocarcin M intercalates into bacteriophage PM2 DNA. It is toxic to rats with an intravenous LD50 value of 450 mg/kg.
UsesGilvocarcin M is the minor analogue of a complex of C-glycoside antitumour actives isolated from a Streptomyces sp.. Gilvocarcin M contains a methyl group in the 8-position, and is less active than the vinyl analogue (gilvocarcin V), which is thought to act as an inhibitor of human topoisomerase II. Gilvocarcin M displays potent antibacterial, antifungal, antiviral and antitumour activity. Recent research suggests that the gilvocarcins act as photoactivated crosslinkers of DNA to histones.
UsesGilvocarcin M is the minor analogue of a complex of C-glycoside antitumor actives isolated from a Streptomyces sp.. Gilvocarcin M contains a methyl group in the 8-position, and is less active than the vinyl analogue (gilvocarcin V), which is thought to act as an inhibitor of human topoisomerase II. Gilvocarcin M displays potent antibacterial, antifungal, antiviral and antitumor activity. Recent research suggests that the gilvocarcins act as photoactivated cross-linkers of DNA to histones.
UsesGilvocarcin M is the minor analogue of Gilvocarcin V with anti-bact, -fungal, -viral and -tumor activity.
Suppliers16 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
孟成科技（上海）有限公司400-820-6829 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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