(1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,14-dione

• ChemBase ID: 1323
• Molecular Formular: C19H26O2
• Molecular Mass: 286.40854
• Monoisotopic Mass: 286.19328007
• SMILES: O=C1[C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)CC3)C)CC2)CC1)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CCC2=O)C)C
• InChI: InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
• InChIKey: AEMFNILZOJDQLW-QAGGRKNESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-ene-5,14-dione; (1S,2R,10R,11S,15S)-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-ene-5,14-dione
• IUPAC Traditional name: androstenedione; 4-androstenedione
• Synonyms: 4-Androstene-3,17-dione; 17-Ketotestosterone; 3,17-Dioxoandrost-4-ene; Fecundin; NSC 9563; SKF 2170; Δ4-Androstene-3,17-dione; (8R,9S,10R,13S,14S)-10,13-dimethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione; 4-ANDROSTENE-3-17-DIONE; 4-Androstenedione; Androstenedione; Androstenedione; 4-Androstene-3,17-dione; 雄烯二酮; 4-雄烯-3,17-二酮

Database IDs

• CAS Number: 1963-5-8; 63-05-8
• EC Number: 200-554-5
• MDL Number: MFCD00003615
• Beilstein Number: 2059239
• PubChem SID: 24869681; 46508011; 160964783
• PubChem CID: 6128
• CHEBI ID: 16422
• CHEMBL: 274826
• Chemspider ID: 5898
• DrugBank ID: DB01536
• IUPHAR ligand ID: 2860
• Unique Ingredient Identifier: 409J2J96VR
• Wikipedia Title: Androstenedione

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.028997
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.928951
• LogD (pH = 7.4): 3.928951
• Log P: 3.928951
• Molar Refractivity: 83.6075 cm^3
• Polarizability: 32.712193 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.93
• LOG S: -4.03
• Solubility (Water): 2.70e-02 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 170-171 °C(lit.); 170-173 °C; 172-174°C
• Optical Rotation: [α]20/D +189±2°, c = 1% in ethanol

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer
• RTECS: BV8150000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Drug Control: USDEA Schedule IIIN; USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

Pharmacology Properties

• Metabolism: Liver
• Legal Status: Schedule III (US)
• Gene Information: human ... HSD17B3(3293)

Product Information

• Purity: ≥98.0% (HPLC); 97%
• Grade: purum; VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C19H26O2

DETAILS

DrugBank - DB07386

Drug information: experimental

DrugBank - DB01536

• Drug Groups: illicit; experimental
• Description: A delta-4 C19 steroid that is produced not only in the testis, but also in the ovary and the adrenal cortex. Depending on the tissue type, androstenedione can serve as a precursor to testosterone as well as estrone and estradiol. [PubChem]

Sigma Aldrich - 10340

Other Notes
Sales restrictions may apply
Biochem/physiol Actions
Testosterone precursor and metabolite with androgenic activity; may increase the risk of prostate or pancreatic cancer.

Sigma Aldrich - 46033

Biochem/physiol Actions
Testosterone precursor and metabolite with androgenic activity; may increase the risk of prostate or pancreatic cancer.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A637550

Testosterone precursor and metabolite with androgenic activity. Controlled substance (anabolic steroid).

REFERENCES

• Walker, V.R., et al.: Anal. Biopchem., 234, 194 (1996)
• King, D.S., et al.: J. Am. Med. Assoc., 281, 2020 (1996)