(10S,13S)-13-(hydroxymethyl)-9-methyl-2-octyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.04,15]pentadeca-1,4,6,8(15)-tetraen-11-one

• ChemBase ID: 156739
• Molecular Formular: C25H39N3O2
• Molecular Mass: 413.59606
• Monoisotopic Mass: 413.3042275
• SMILES: CCCCCCCCc1c2c3c([nH]1)cccc3N([C@H](C(=O)N[C@@H](C2)CO)C(C)C)C
• Canonical SMILES: CCCCCCCCc1[nH]c2c3c1C[C@@H](CO)NC(=O)[C@@H](N(c3ccc2)C)C(C)C
• InChI: InChI=1S/C25H39N3O2/c1-5-6-7-8-9-10-12-20-19-15-18(16-29)26-25(30)24(17(2)3)28(4)22-14-11-13-21(27-20)23(19)22/h11,13-14,17-18,24,27,29H,5-10,12,15-16H2,1-4H3,(H,26,30)/t18-,24-/m0/s1
• InChIKey: VLJISOQUPIAQHH-UUOWRZLLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,13S)-13-(hydroxymethyl)-9-methyl-2-octyl-10-(propan-2-yl)-3,9,12-triazatricyclo[6.6.1.0^4,^1^5]pentadeca-1,4,6,8(15)-tetraen-11-one
• IUPAC Traditional name: (10S,13S)-13-(hydroxymethyl)-10-isopropyl-9-methyl-2-octyl-3,9,12-triazatricyclo[6.6.1.0^4,^1^5]pentadeca-1,4,6,8(15)-tetraen-11-one
• Synonyms: (-)-7-Octylindolactam V

Database IDs

• CAS Number: 109346-66-9
• MDL Number: MFCD00135799
• Beilstein Number: 4765509
• PubChem SID: 162250876; 24886783
• PubChem CID: 45934410

CALCULATED PROPERTIES

• Acid pKa: 13.134158
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): 5.3300767
• LogD (pH = 7.4): 5.330076
• Log P: 5.330077
• Molar Refractivity: 124.4179 cm^3
• Polarizability: 49.015873 Å^3
• Polar Surface Area: 68.36 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: mouse ... Prkcd(18753)rat ... IGHV3-33(28434)

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C25H39N3O2

DETAILS

Sigma Aldrich - 75077

Analysis Note
NMR-spectrum: 3 impurity peaks
Other Notes
Synthetic analog of teleocidin A1, a tumor promoter in nanomolar conc.1