[(1R,4aS,10aR)-1,4a-dimethyl-7-propyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methanamine

• ChemBase ID: 165591
• Molecular Formular: C20H31N
• Molecular Mass: 285.46684
• Monoisotopic Mass: 285.24565
• SMILES: C1C[C@]([C@H]2[C@](C1)(c1c(CC2)cc(cc1)CCC)C)(CN)C
• Canonical SMILES: CCCc1ccc2c(c1)CC[C@@H]1[C@]2(C)CCC[C@@]1(C)CN
• InChI: InChI=1S/C20H31N/c1-4-6-15-7-9-17-16(13-15)8-10-18-19(2,14-21)11-5-12-20(17,18)3/h7,9,13,18H,4-6,8,10-12,14,21H2,1-3H3/t18-,19-,20+/m0/s1
• InChIKey: GWCJWLXMNCMNTG-SLFFLAALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R,4aS,10aR)-1,4a-dimethyl-7-propyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl]methanamine
• IUPAC Traditional name: [(1R,4aS,10aR)-1,4a-dimethyl-7-propyl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine
• Synonyms: (1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl-1-phenanthrenemethanamine); 13-Isopropyl-podocarpa-8,11,13-trien-15-amine; (+)-Dehydroabiethylamine; NSC 2955; Leelamine; Dehydroabiethylamine

Database IDs

• CAS Number: 1446-61-3
• PubChem SID: 162259724
• PubChem CID: 29976790

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.3119466
• LogD (pH = 7.4): 2.934243
• Log P: 5.3269687
• Molar Refractivity: 91.2114 cm^3
• Polarizability: 36.024654 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D229080

Dehydroabiethylamine is a primary amine with high molecular weight; shows a strong antibiotic effect with a broad spectrum of activity against Staphylococcus p.a. (sic), Escherichia coli, Mycobacterium tuberculosis, and Candida albicans.

REFERENCES

• Ohta, M., et al.: Chem. Pharmac. Bull., 4, 273 (1956)