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RHIZOXIN

AlkaPlorer ID: AK001593

Synonym: '4,7,12,18-Tetraoxatetracyclo15.3.1.03,5.011,13 heneicos-14-ene-6,19-dione, 10-hydroxy-8-2-methoxy- 1,3,7-trimethyl-8-(2-methyl-4-oxazolyl)-3,5,7- octatrienyl-11,16-dimethyl-, 1S-1R*,3R*,5S*, 8R*(1R*,2S*,3E,5E,7E),10R*,11S*,13S*,14E,16S*,17S*-', 'Rhizoxin', 'WF 1360', 'NSC 332598', 'RHIZOXIN'

IUPAC Name: (1S,3S,5R,8S,10S,11R,13R,14E,16R,17R)-10-hydroxy-8-[(2S,3R,4E,6E,8E)-3-methoxy-4,8-dimethyl-9-(2-methyl-1,3-oxazol-4-yl)nona-4,6,8-trien-2-yl]-11,16-dimethyl-4,7,12,18-tetraoxatetracyclo[15.3.1.03,5.011,13]henicos-14-ene-6,19-dione

Structure

SMILES: CO[C@@H](/C(C)=C/C=C/C(C)=C/C1=COC(C)=N1)[C@@H](C)[C@@H]1C[C@H](O)[C@@]2(C)O[C@@H]2/C=C/[C@@H](C)[C@H]2C[C@H](CC(=O)O2)C[C@@H]2O[C@H]2C(=O)O1

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InChI: InChI=1S/C35H47NO9/c1-19(13-25-18-41-23(5)36-25)9-8-10-21(3)32(40-7)22(4)27-17-29(37)35(6)30(45-35)12-11-20(2)26-14-24(16-31(38)42-26)15-28-33(43-28)34(39)44-27/h8-13,18,20,22,24,26-30,32-33,37H,14-17H2,1-7H3/b9-8+,12-11+,19-13+,21-10+/t20-,22+,24+,26-,27+,28+,29+,30-,32+,33-,35-/m1/s1

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InChIKey: OWPCHSCAPHNHAV-QIPOKPRISA-N

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Source

Species Genus Family Order Class Phylum Kingdom Domain
Rhizopus microsporus Rhizopus Rhizopodaceae Mucorales Mucoromycetes Mucoromycota Fungi Eukaryota

Properties Information

Molecule Weight: 625.7590000000002

TPSA？: 133.15

MolLogP？: 5.0454200000000045

Number of H-Donors: 1

Number of H-Acceptors: 10

RingCount: 5

Activities Information

Organism Target Name Standard Type Standard Value Standard Units doi
Cryptococcus gattii Cryptococcus bacillisporus Activity nan None 10.1128/aac.00153-10
Homo sapiens BJ IC50 50000.0 nM 10.1016/j.bmcl.2010.01.009
Homo sapiens HEK293 IC50 350.0 nM 10.1016/j.bmcl.2010.01.009
Homo sapiens HepG2 IC50 400.0 nM 10.1016/j.bmcl.2010.01.009
Homo sapiens Raji IC50 340.0 nM 10.1016/j.bmcl.2010.01.009
Mus musculus Cyclooxygenase-2 IC50 nan None 10.1016/j.bmcl.2010.01.009
Mus musculus Mus musculus t1/2 nan None 10.1016/j.bmcl.2010.01.009
Ovis aries Cyclooxygenase-1 IC50 nan None 10.1016/j.bmcl.2010.01.009
Sus scrofa Tubulin Inhibition 81.0 % 10.1016/j.bmcl.2006.06.091
Trypanosoma brucei brucei Trypanosoma brucei brucei IC50 150.0 nM 10.1016/j.bmcl.2010.01.009
Trypanosoma brucei brucei Trypanosoma brucei brucei Inhibition nan % 10.1016/j.bmcl.2010.01.009
None ADMET Ratio 100.0 None 10.1016/j.bmcl.2010.01.009
None NON-PROTEIN TARGET Hepatotoxicity (acute) 0.0 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (animal toxicity known) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (benign tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (granulomatous hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (mechanism) nan None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 1.0 None 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (moderate) 7.3 % 10.1016/s0399-8320(04)95062-2
None NON-PROTEIN TARGET Hepatotoxicity (time to onset) nan None 10.1016/s0399-8320(04)95062-2
None No relevant target T1/2 24.0 hr 10.1016/j.bmcl.2010.01.009
None Unchecked Hepatotoxicity (acute) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (association with vascular disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (choleostasis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (chronic liver disease) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cirrhosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (comment) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (cytolytic) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (malignant tumour) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (severe hepatitis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (steatosis) 0.0 None 10.1016/s0399-8320(04)95062-2
None Unchecked Hepatotoxicity (successful reintroduction) nan None 10.1016/s0399-8320(04)95062-2
None Unchecked IC50 150.0 nM 10.1016/j.bmcl.2010.01.009
None Unchecked IC50 6800.0 nM 10.1021/jm3009629
None Unchecked Inhibition 102.0 % 10.1016/j.bmcl.2010.01.009
None Unchecked Ratio 100.0 None 10.1016/j.bmcl.2010.01.009

Metabolism Information