(2R,3R,4aR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-2H,3H,4H,4aH,6H-benzo[c]chromen-6-one

• ChemBase ID: 131969
• Molecular Formular: C15H16O6
• Molecular Mass: 292.28394
• Monoisotopic Mass: 292.09468823
• SMILES: C[C@@]12C[C@H]([C@@H](C=C1c1cc(cc(c1C(=O)O2)O)OC)O)O
• Canonical SMILES: COc1cc(O)c2c(c1)C1=C[C@@H](O)[C@@H](C[C@]1(OC2=O)C)O
• InChI: InChI=1S/C15H16O6/c1-15-6-12(18)10(16)5-9(15)8-3-7(20-2)4-11(17)13(8)14(19)21-15/h3-5,10,12,16-18H,6H2,1-2H3/t10-,12-,15-/m1/s1
• InChIKey: MMHTXEATDNFMMY-IXPVHAAZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4aR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-2H,3H,4H,4aH,6H-benzo[c]chromen-6-one
• IUPAC Traditional name: (2R,3R,4aR)-2,3,7-trihydroxy-9-methoxy-4a-methyl-2H,3H,4H-benzo[c]chromen-6-one
• Synonyms: Altenuene from Alternaria sp.; (2R,3R,4aR)-2,3,4,4a-Tetrahydro-2,3,7-trihydroxy-9-methoxy-4a-methyl-6H-dibenzo[b,d]pyran-6-one; (-)-Altenuene

Database IDs

• CAS Number: 889101-41-1; 29752-43-0
• MDL Number: MFCD00133067
• PubChem SID: 24890865; 162226246
• PubChem CID: 11645000

CALCULATED PROPERTIES

• Acid pKa: 9.499075
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.0034201
• LogD (pH = 7.4): 1.000049
• Log P: 1.0034633
• Molar Refractivity: 74.2948 cm^3
• Polarizability: 28.615278 Å^3
• Polar Surface Area: 96.22 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: HP8758000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 61-26/27/28
• Safety Statements: 36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H330-H360
• GHS Precautionary statements: P201-P260-P264-P280-P284-P302 + P350
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

DETAILS

Toronto Research Chemicals - A575740

(-)-Altenuene is a toxin isolated from the fungus Alternaria tenuis. (-)-Altenuene is structurally related to Alternariol (A575760).

REFERENCES

• Pero, W.R. et al.: Biochim. Biophys. Acta, 230, 170 (1971)
• Altemoller, M. et al.: J. Nat. Prod., 72, 1288 (1971)