Reverse engineering chemical structures from molecular descriptors : how many solutions?

Journal Article · Wed Jun 01 04:00:00 EDT 2005 · Proposed for publication in the Journal of Computer Aided Molecular Design.

OSTI ID:970736

Brown, William Michael ^[1]; Martin, Shawn Bryan ^[1]; Faulon, Jean-Loup Michel

---

1. Sandia National Laboratories, Albuquerque, NM

Physical, chemical and biological properties are the ultimate information of interest for chemical compounds. Molecular descriptors that map structural information to activities and properties are obvious candidates for information sharing. In this paper, we consider the feasibility of using molecular descriptors to safely exchange chemical information in such a way that the original chemical structures cannot be reverse engineered. To investigate the safety of sharing such descriptors, we compute the degeneracy (the number of structure matching a descriptor value) of several 2D descriptors, and use various methods to search for and reverse engineer structures. We examine degeneracy in the entire chemical space taking descriptors values from the alkane isomer series and the PubChem database. We further use a stochastic search to retrieve structures matching specific topological index values. Finally, we investigate the safety of exchanging of fragmental descriptors using deterministic enumeration.

• Research Organization: Sandia National Laboratories
• Sponsoring Organization: USDOE
• DOE Contract Number: AC04-94AL85000
• OSTI ID: 970736
• Report Number(s): SAND2005-3367J
• Journal Information: Proposed for publication in the Journal of Computer Aided Molecular Design., Journal Name: Proposed for publication in the Journal of Computer Aided Molecular Design.
• Country of Publication: United States
• Language: English

Related Subjects

74 ATOMIC AND MOLECULAR PHYSICS
99 GENERAL AND MISCELLANEOUS
ALKANES
ENGINEERS
ISOMERS
SAFETY