8,11-Ethanofuro[2,3-e]naphtho[2,3-c:6,7-c']dipyran-2,6,13(9H)-trione,3,3a,5,8,11,13b-hexahydro-7,8,12,15-tetrahydroxy-5,9-dimethyl-,(3aS,5S,8S,9R,11R,13bS,15R)-

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Names

[ CAS No. ]:
19879-06-2

[ Name ]:
8,11-Ethanofuro[2,3-e]naphtho[2,3-c:6,7-c']dipyran-2,6,13(9H)-trione,3,3a,5,8,11,13b-hexahydro-7,8,12,15-tetrahydroxy-5,9-dimethyl-,(3aS,5S,8S,9R,11R,13bS,15R)-

[Synonym ]:
Antibiotic WR 141
WR-141
(3aS)-7,8,12,15syn-Tetrahydroxy-5c,9c-dimethyl-(3ar,13bc)-3,3a,5,8,11,13b-hexahydro-9H-8t,11t-aethano-furo[3,2-c]isochromeno[7,6-g]isochromen-2,6,13-trion
(3aS)-7,8,12,15syn-tetrahydroxy-5c,9c-dimethyl-(3ar,13bc)-3,3a,5,8,11,13b-hexahydro-9H-8t,11t-ethano-furo[3,2-c]isochromeno[7,6-g]isochromene-2,6,13-trione
Granaticin A
Antibiotic WR-141
Litmomycin
Granatcin-A
Granatomycin C

Chemical & Physical Properties

[ Density]:
1.77g/cm3

[ Boiling Point ]:
748.3ºC at 760mmHg

[ Molecular Formula ]:
C22H20O10

[ Molecular Weight ]:
444.38800

[ Flash Point ]:
266.8ºC

[ Exact Mass ]:
444.10600

[ PSA ]:
159.82000

[ LogP ]:
0.28820

[ Vapour Pressure ]:
1.6E-23mmHg at 25°C

[ Index of Refraction ]:
1.745

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MD9100000
CHEMICAL NAME :
Granaticin
CAS REGISTRY NUMBER :
19879-06-2
LAST UPDATED :
199512
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C22-H20-O10
MOLECULAR WEIGHT :
444.42
WISWESSER LINE NOTATION :
T F5 E6 C6666/RW 2AQ W DV GOV KO NV TOTT&&TTJ BQ L1 PQ RQ S1 WQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
38 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
Mutation test systems - not otherwise specified
TEST SYSTEM :
Bacteria - Bacillus subtilis
DOSE/DURATION :
600 nmol/L
REFERENCE :
ZBPHA6 Zentralblatt fuer Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene, Abteilung I: Medizinisch-Hygienische Bakteriologie, Virusforschung und Parasitologie, Originale. (Stuttgart, Fed. Rep. Ger.) V.31-216, 1902-71. For publisher information, see ZMMPAO. Volume(issue)/page/year: 212,259,1969

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

  • (3aR*,5R*,8R*,9S*,11S*,13bR*,15S*)-8,9-dihydroxy-6,7,12,13-tetramethoxy-5,15-dimethyl-3,3a,5,8,9,10,11,13b-octahydro-11,8-(epoxymethano)-2H-furo[3,2-b]anthra[2,3-d]pyran-2-one

DownStream

Related Compounds

  • 1-(4-fluorophenyl)-5-[(4-methoxyphenoxy)methyl]-1H-tetrazole
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-(Isoquinolin-7-yl)ethanamine
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine