CCL: Smiles convention for stereoisomers ?



 Sent to CCL by: Michel Petitjean [petitjean.chiral_+_gmail.com]
 Hi there,
 Does anybody know about the exact convention to specify atoms
 positions from a SMILES having stereocenters in rings ?
 It seems there is a difference in treatment for ring closure and other atoms ?
 For instance for C[C|,||,|H]1C[C|,||,|H](O)CC(=O)O1
 For the second center, not a ring closure, we look from the CC bond,
 and we have H,O,C clockwise.
 For the first one how does one proceed ?
 If one looks from first C to second C, then H, C, O should be
 positioned clockwise, whereas actually it seems it is
 countercloskwise.
 Idem from the example on their site :
 http://www.daylight.com/dayhtml/doc/theory/theory.smiles.html
 C[C|,|H]1CCCCO1
 I could not understand the few sentences on SMILES theory related to
 ring closure digit appearance.
 Thanks by advance
 Michel Petitjean.