4-[(1S,2S,5S,7S,10R,11R,14R,15S,16R)-5,11,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one

• ChemBase ID: 3327
• Molecular Formular: C23H34O5
• Molecular Mass: 390.51306
• Monoisotopic Mass: 390.24062419
• SMILES: C[C@]12CC[C@H](O)C[C@@H]1CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2(C)[C@H](CC[C@@]12O)C1=CC(=O)OC1
• Canonical SMILES: O[C@H]1CC[C@]2([C@H](C1)CC[C@@H]1[C@@H]2C[C@@H](O)[C@]2([C@@]1(O)CC[C@@H]2C1=CC(=O)OC1)C)C
• InChI: InChI=1S/C23H34O5/c1-21-7-5-15(24)10-14(21)3-4-17-18(21)11-19(25)22(2)16(6-8-23(17,22)27)13-9-20(26)28-12-13/h9,14-19,24-25,27H,3-8,10-12H2,1-2H3/t14-,15-,16+,17+,18-,19+,21-,22-,23+/m0/s1
• InChIKey: SHIBSTMRCDJXLN-VXSBHOQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(1S,2S,5S,7S,10R,11R,14R,15S,16R)-5,11,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-2,5-dihydrofuran-2-one
• IUPAC Traditional name: 4-[(1S,2S,5S,7S,10R,11R,14R,15S,16R)-5,11,16-trihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadecan-14-yl]-5H-furan-2-one
• Synonyms: 4-(3,12,14-Trihydroxy-10,13-Dimethyl-Hexadecahydro-Cyclopenta[a]Phenanthren-17-Yl)-5h-Furan-2-One

Database IDs

• PubChem SID: 160966768; 46509019
• PubChem CID: 46936752

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.1511164
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.8269637
• LogD (pH = 7.4): 1.3943652
• Log P: 1.8365436
• Molar Refractivity: 105.1561 cm^3
• Polarizability: 41.84968 Å^3
• Polar Surface Area: 86.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.6
• LOG S: -3.79
• Solubility (Water): 6.32e-02 g/l

DETAILS

DrugBank - DB03671

• Drug Groups: experimental
• Description: 3 beta,12 beta,14-Trihydroxy-5 beta-card-20(22)-enolide. A cardenolide which is the aglycon of digoxin. Can be obtained by hydrolysis of digoxin or from Digitalis orientalis L. and Digitalis lanata Ehrh. [PubChem]