(1S,2R,10S,11S,15R)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-6,13-dien-5-one

• ChemBase ID: 160608
• Molecular Formular: C19H26O
• Molecular Mass: 270.40914
• Monoisotopic Mass: 270.19836545
• SMILES: C1C(=O)C=C2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C=CC2)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC=C2)C)C
• InChI: InChI=1S/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3/t15-,16-,17-,18-,19-/m0/s1
• InChIKey: HNDHDMOSWUAEAW-VMXHOPILSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,15R)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,13-dien-5-one
• IUPAC Traditional name: androstadienone
• Synonyms: Androsta-4,16-dien-3-one; 4,16-Androstadien-3-one; NSC 93234; Δ4,16-Androstadien-3-one; Androstadienone

Database IDs

• CAS Number: 4075-07-4
• PubChem SID: 162254743
• PubChem CID: 92979

CALCULATED PROPERTIES

• Acid pKa: 19.081135
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.2343125
• LogD (pH = 7.4): 4.2343125
• Log P: 4.2343125
• Molar Refractivity: 84.0309 cm^3
• Polarizability: 32.423042 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A637340

Androstadienone is a prominent androstene present on male human axillary hair and on the male axillary skin surface. Studies suggest that Androstadienone has a strong pheromone-like activities in humans. Androstadienone is a metabolite of Testosterone (T

REFERENCES

• Grosser, B.I. et al.: Psychoneuroendocrinology, 25, 289 (2000)
• Gulyas, B. et al.: Neurochem. Int., 44, 595 (2000)
• Hummer, T.A. et al.: Horm. Behav., 55, 548 (2000)
• Stylianou, M. et al.: J. Biol. Chem., 236, 692 (2000)