[(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydro(9,9,10,10-2H4)phenanthren-1-yl]methanamine

• ChemBase ID: 165593
• Molecular Formular: C20H31N
• Molecular Mass: 285.46684
• Monoisotopic Mass: 285.24565
• SMILES: C1C[C@]([C@H]2[C@](C1)(c1c(CC2)cc(cc1)C(C)C)C)(CN)C
• Canonical SMILES: NC[C@]1(C)CCC[C@]2([C@H]1CCc1c2ccc(c1)C(C)C)C
• InChI: InChI=1S/C20H31N/c1-14(2)15-6-8-17-16(12-15)7-9-18-19(3,13-21)10-5-11-20(17,18)4/h6,8,12,14,18H,5,7,9-11,13,21H2,1-4H3/t18-,19-,20+/m0/s1
• InChIKey: JVVXZOOGOGPDRZ-SLFFLAALSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydro(9,9,10,10-^2H₄)phenanthren-1-yl]methanamine
• IUPAC Traditional name: [(1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-2,3,4,10a-tetrahydro(9,9,10,10-^2H₄)phenanthren-1-yl]methanamine
• Synonyms: (1R,4aS,10aR)-1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl-1-phenanthrenemethanamine)-d4 Hydrochloride; 13-Isopropyl-podocarpa- 8,11,13-trien-15-amine-d4 Hydrochloride; (+)-Dehydroabiethylamine-d4 Hydrochloride; NSC 2955-d4 Hydrochloride; Dehydroabiethylamine-d4 Hydrochloride

Database IDs

• PubChem SID: 162259726
• PubChem CID: 71315291

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 2.154397
• LogD (pH = 7.4): 2.7766933
• Log P: 5.1694193
• Molar Refractivity: 91.159 cm^3
• Polarizability: 36.10561 Å^3
• Polar Surface Area: 26.02 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D229082

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)