(3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14,16,18-heptaen-13-one

• ChemBase ID: 129620
• Molecular Formular: C18H12O6
• Molecular Mass: 324.28428
• Monoisotopic Mass: 324.0633881
• SMILES: COc1c2c(c3[C@@H]4C=CO[C@@H]4Oc3c1)oc1c(c2=O)c(ccc1)O
• Canonical SMILES: COc1cc2O[C@@H]3[C@H](c2c2c1c(=O)c1c(o2)cccc1O)C=CO3
• InChI: InChI=1S/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3/t8-,18+/m0/s1
• InChIKey: UTSVPXMQSFGQTM-DCXZOGHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,7R)-15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0^2,^9.0^3,^7.0^1^4,^1^9]icosa-1,4,9,11,14,16,18-heptaen-13-one
• IUPAC Traditional name: sterigmatocystin
• Synonyms: Sterigmatocystin; Sterigmatocystin; (3aR,12cS)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one; 3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one; (3aR-cis)-3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one; NSC 201423; NSC 204985; Sterigmatocystine

Database IDs

• CAS Number: 10048-13-2
• PubChem SID: 162223910
• PubChem CID: 5280389
• CHEMBL: 524291
• Chemspider ID: 4447522
• KEGG ID: C00961
• Wikipedia Title: Sterigmatocystin

CALCULATED PROPERTIES

• Acid pKa: 9.582689
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.098556
• LogD (pH = 7.4): 3.095771
• Log P: 3.0985918
• Molar Refractivity: 83.7026 cm^3
• Polarizability: 32.183052 Å^3
• Polar Surface Area: 74.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Safety Statements: R

DETAILS

Toronto Research Chemicals - S686710

Sterigmatocystin is a carcinogenic mycotoxin that is struturally related to Aflatoxin. Sterigmatocystin has been shown to inhibit RNA synthesis in rat liver nuclei.

REFERENCES

• Nel, W. et al.: Biochem. Pharmacol., 19, 957 (1970)
• Purchase, I.F.H. et al.: Food Cosm. Toxicol., 8, 289 (1970)